(-)-Camphanic acid chloride Basic Product Information

Product Name	(-)-Camphanic acid chloride	CAS	39637-74-6
Synonyms	2-Oxabicyclo[2.2.1]heptane-1-carbonylchloride, 4,7,7-trimethyl-3-oxo-, (1S)-;(-)-(1S)-Camphanoyl chloride;(-)-(1S,4R)-Camphanoyl chloride;(-)-(S)-Camphanyl chloride;(-)-Camphanic acidchloride;(-)-Camphanic chloride;(-)-Camphanylchloride;(1S)-(-)-Camphanic acid chloride;(1S)-(-)-Camphanic chloride;(1S)-(-)-Camphanoyl chloride;(1S)-(-)-Camphanylchloride;(1S)-(-)-w-Camphanic chloride;(1S)-Camphanoyl chloride;(1S,4R)-(-)-Camphanic acidchloride;(1S,4R)-w-Camphanoyl chloride;(S)-Camphanic acid chloride;(S)-Camphanoylchloride;	Molecular Formula	C10H13ClO3
EINECS Number	254-552-4	Molecular Structure
Appearance	Light Yellow Powder
Purity
Supply Ability

(-)-Camphanic acid chloride Quality documents

(-)-Camphanic acid chloride Appearance/Package/Shipping/Storage

package

storage condition

Store in cool & dry place,Keep away from strong light and heat

(-)-Camphanic acid chloride Application

(-)-Camphanic acid chloride literature

188. Bestimmung des Chiralitaetssinns der enantiomeren 2,6-Adamantandiole

Gerlach, Hans

, p. 1815 - 1821 (1985)

The enantiomers of 2,6-adamantanediol (1) are resolved via the diastereoisomeric camphanoates.The (2R,6R)-chirality sense for (-)-1 and (2S,6S) for (+)-1 was determined by chemical correlation with (-)-(1R,5R)-bicyclo<3.3.1>nonan-2,6-dion((1R,5R)-3) of known absolute configuration in the following way: alkylation of the bis(pyrrolidine enamine) of (-)-(1R,5R)-3 with CD2I2 and hydrolysis of the product gives the enantiomer 4 of (4,4-D2)-2,6-adamantanedione.Reduction of 4 with LiAlH4 leads to one enantiomer (Scheme 2) of each of the three diols 5-7 of known absolute configuration.The three diols are themselves configurational isomers due to the presence of the CD2 group, but correspond otherwise entirely to the enantiomeric diols 1.Accordingly, they can also be separated by means of their diastereoisomeric camphanoates to give the diols 5/6 and 7.These samples are easily distinguished and identified by their characteristic 1H-NMR spectra (cf.Fig. 2.).This allows to identify the (2R,6R)- and (2S,6S)-enantiomer of 1 on the basis of their behaviour in the resolution experiment analogous to that of the diols 5/6 and 7, respectively.The diol (-)-1 must have the (2R,6R)-configuration because it forms, like the diols 5/6, with (-)-camphanic acid the diastereoisomeric ester less soluble in benzene.The diol (+)-1 has (2S,6S)-configuration, because it forms, like 7, with (+)-camphanic acid the diastereoisomeric ester less soluble in benzene.The bis(4-methoxybenzoate) of (-)-(2R,6R)-1 shows chiroptical properties which are in accordance with Nakanishi's rule for two chromophores having coupled electric dipol transition moments arranged with a left handed torsion angle.

Chiral bisphosphine ligands based on quinoline oligoamide foldamers: application in asymmetric hydrogenation

Zheng, Lu,Zheng, Dan,Wang, Yanru,Yu, Chengyuan,Zhang, Kun,Jiang, Hua

supporting information, p. 9573 - 9577 (2019/11/20)

A series of chiral bisphosphine ligands were designed and synthesized based on single-handed quinoline oligoamide foldamers. The bisphosphine ligands can coordinate with Rh(cod)₂BF₄ in a 1 : 1 stoichiometry and the resulted chiral Rh(i) catalysts were applied in the asymmetric hydrogenation of α-dehydroamino acid esters, in which excellent conversions and promising levels of enantioselectivity were achieved.

Irreversible Cysteine-Selective Protein Labeling Employing Modular Electrophilic Tetrafluoroethylation Reagents

Václavík, Ji?í,Zschoche, Reinhard,Klimánková, Iveta,Matou?ek, Václav,Beier, Petr,Hilvert, Donald,Togni, Antonio

supporting information, p. 6490 - 6494 (2017/05/15)

Fluoroalkylation reagents based on hypervalent iodine are widely used to transfer fluoroalkyl moieties to various nucleophiles. However, the transferred groups have so far been limited to simple structural motifs. We herein report a reagent featuring a secondary amine that can be converted to amide, sulfonamide, and tertiary amine derivatives in one step. The resulting reagents bear manifold functional groups, many of which would not be compatible with the original synthetic pathway. Exploiting this structural versatility and the known high reactivity toward thiols, the new-generation reagents were used in bioconjugation with an artificial retro-aldolase, containing an exposed cysteine and a reactive catalytic lysine. Whereas commercial reagents based on maleimide and iodoacetamide labeled both sites, the iodanes exclusively modified the cysteine residue. The study thus demonstrates that modular fluoroalkylation reagents can be used as tools for cysteine-selective bioconjugation.

Asymmetric (4+3) cycloadditions of enantiomerically enriched epoxy enolsilanes

Lo, Brian,Lam, Sarah,Wong, Wing-Tak,Chiu, Pauline

supporting information, p. 12120 - 12123 (2013/01/16)

A f(oxy) allyl: The intermolecular (4+3) cycloaddition of enantiomerically enriched epoxy enolsilanes produces cycloadducts with up to 99 % ee, thus implying the reaction does not proceed by the putative achiral oxyallyl cation intermediate, but through a transiently chiral electrophile which retains the stereochemical information of the epoxide (see scheme; TES=triethylsilyl, Tf=trifluoromethanesulfonyl). Copyright

Synthesis and resolution of 2,2-dimethyl-1,3-diphenyl-1,3-propanediol, a new C₂-symmetric and conformationally rigid acyclic diol

Bhowmick,Prasad,Joshi

, p. 851 - 855 (2007/10/03)

Diastereomerically pure (+)- and (-)-2,2-dimethyl-1,3-diphenyl-1,3-propanediols were synthesized starting from diethyl malonate and resolved through diesters of (-)-camphanic acid and also N-carbethoxy-L-proline. The absolute configuration of the (-)-enantiomer was established by X-ray crystallography.

(-)-Camphanic acid chloride Upstream and downstream

39637-74-6 Upstream product

• 67111-66-4

  (-)-camphanic acid 

• 48138-74-5

  1,2,2-trimethyl-cyclopentane-1,3-dicarbonyl chloride 

• 10333-96-7

  1-Bromo-5,8,8-trimethyl-3-oxa-bicyclo[3.2.1]octane-2,4-dione 

• 124-83-4

  (+)-camphoric acid 

• 124-83-4

  D-(+)-camphoric acid 

39637-74-6 Downstream Products

• 119874-36-1

  1-O-(tert-butyldiphenylsilyl)-4-O-camphanyl-2,3:5,6-di-O-isopropylidene-D-myo-inositol 

• 119874-36-1

  3-O-(tert-butyldiphenylsilyl)-6-O-camphanyl-1,2:4,5-di-O-isopropylidene-D-myo-inositol 

• 131147-10-9

  4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (3aR,4R,5S,6R,7R,7aR)-5,6,7-tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester 

• 131147-10-9

  4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (3aS,4S,5R,6S,7S,7aS)-5,6,7-tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester 

• 131146-82-2

  C₅₄H₆₀O₁₂ 

• 131146-82-2

  C₅₄H₆₀O₁₂ 

• 131147-17-6

  C₅₄H₆₀O₁₂ 

• 131147-17-6

  C₅₄H₆₀O₁₂ 

Related Products

• 

  2-Methyl anthraquinone

  CAS NO.：

  84-54-8

  Molecular Formula ：

  C15H10O2

• 

  CAMPESTEROL

  CAS NO.：

  474-62-4

  Molecular Formula ：

  C28H48O

• 

  Macroporous Strong Base Anion Exchange Resin

  CAS NO.：

  Macroporous Strong Base Anion Exchange Resin

  Molecular Formula ：

• 

  Hydroxylapatite

  CAS NO.：

  1306-06-5

  Molecular Formula ：

  Ca5HO13P3

• 

  2-Methyl anthraquinone

  CAS NO.：

  84-54-8

  Molecular Formula ：

  C15H10O2