(+)-(1R,3R)-2,2-dichloro-3-phenylcyclopropanecarboxylic acid | 646995-57-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+)-(1R,3R)-2,2-dichloro-3-phenylcyclopropanecarboxylic acid
• 英文别名: (1R,3R)-2,2-dichloro-3-phenylcyclopropane-1-carboxylic acid
• CAS: 646995-57-5
• 化学式: C₁₀H₈Cl₂O₂
• 分子量: 231.078
• InChiKey: XWUCXKKIVKFJSF-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-(1R,3R)-2,2-dichloro-3-phenylcyclopropanecarboxylic acid 在 sodium tetrahydroborate 、 potassium phosphate buffer 、 Rhodococcus sp. AJ₂₇₀ cells 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 (-)-(1R,2R)-2-phenylcyclopropanecarboxamide
  参考文献：
  名称：

  Synthesis of high enantiomeric purity gem-dihalocyclopropane derivatives from biotransformations of nitriles and amides

  摘要：

  Enantioselective biotransformations of geminally dihalogenated cyclopropanecarbonitriles and amides are described. Both the reaction rate and enantioselectivity of the nitrile hydratase and amidase involved in Rhodococcus sp. AJ270 microbial cells are strongly governed by the nature of gein-disubstituents on the cyclopropane ring; the amidase generally exhibits steric dependence on the substituents while both the steric and electronic factors of the substituents may affect the action of the nitrile hydratase. The match of steric bulkiness of the substituents at 2- with that at 3-positions on the cyclopropane ring benefits the efficient and highly enantioselective reaction. Coupled with facile chemical transformations, biocatalytic transformations of nitrile and amide supply an effective synthesis of optically active 2,2-disubstitued-3-phenylcyclopropanecarboxylic acid and amide in both enantiomeric forms. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.016
• 作为产物：
  描述：

  (E)-(3,3-二乙氧基-1-丙烯基)苯 在 potassium phosphate buffer 、 Rhodococcus sp. AJ₂₇₀ cells 作用下， 反应 8.0h， 生成 (+)-(1R,3R)-2,2-dichloro-3-phenylcyclopropanecarboxylic acid
  参考文献：
  名称：

  Synthesis of high enantiomeric purity gem-dihalocyclopropane derivatives from biotransformations of nitriles and amides

  摘要：

  Enantioselective biotransformations of geminally dihalogenated cyclopropanecarbonitriles and amides are described. Both the reaction rate and enantioselectivity of the nitrile hydratase and amidase involved in Rhodococcus sp. AJ270 microbial cells are strongly governed by the nature of gein-disubstituents on the cyclopropane ring; the amidase generally exhibits steric dependence on the substituents while both the steric and electronic factors of the substituents may affect the action of the nitrile hydratase. The match of steric bulkiness of the substituents at 2- with that at 3-positions on the cyclopropane ring benefits the efficient and highly enantioselective reaction. Coupled with facile chemical transformations, biocatalytic transformations of nitrile and amide supply an effective synthesis of optically active 2,2-disubstitued-3-phenylcyclopropanecarboxylic acid and amide in both enantiomeric forms. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.016

文献信息

• Nitrile and Amide Biotransformations for Efficient Synthesis of Enantiopure gem-Dihalocyclopropane Derivatives
  作者：Mei-Xiang Wang、Guo-Qiang Feng、Qi-Yu Zheng

  DOI：10.1002/adsc.200303020

  日期：2003.6

  the cells were strongly determined by the nature of the halogen substituent. The synthetic utility of the biocatalytic process was illustrated by an efficient and multi-gram scale biotransformation and synthesis of enantiopure 2,2-dichloro-3-phenylcyclopropanecarboxylic acid and amide in both enantiomeric forms.

  由Rhodococcus sp。催化。在非常温和的条件下，对AJ270微生物细胞，反式-2,2-二卤代-3-苯基环丙烷腈和-酰胺进行对映体选择性水解。细胞中涉及的腈水合酶和酰胺酶的效率和对映选择性都强烈地取决于卤素取代基的性质。生物催化过程的合成效用通过对映体形式的对映纯2，2-二氯-3-苯基环丙烷羧酸和酰胺的高效，数克规模的生物转化和合成得到了说明。
• Synthesis of 2,5-Diaryl-3-halofurans via Regioselective Ring Cleavage of Aryl 3-Aryl-2,2-dihalocyclopropyl Ketones
  作者：Yoo Tanabe、Ken-ichi Wakimura、Yoshinori Nishii、Yukari Muroya

  DOI：10.1055/s-1996-4218

  日期：1996.3

  Several aryl 3-aryl-2,2-dihalocyclopropyl ketones were converted to 2,5-diaryl-3-halofurans in the presence of aluminum chloride via regioselective gem-dihalocyclopropane ring cleavage. Friedel-Crafts acylation of substituted benzenes with 3-aryl-2,2-dihalocyclopropanecarbonyl chlorides followed by this furan formation also proceeded in a one-pot manner. For functionalization, bromine on a furan ring was easily replaced by methyl and carboxyl groups; lithiation using butyllithium followed by the treatment with iodomethane and carbon dioxide, respectively.

  在有氯化铝存在的情况下，通过区域选择性的宝石-二环丙烷环裂解，一些芳基 3-芳基-2,2-二环丙基酮被转化为 2,5-二芳基-3-卤呋喃。用 3-芳基-2,2-二卤代环丙烷羰酰氯对取代苯进行弗里德尔-卡夫酰化，然后形成呋喃，也是以一锅法进行的。在官能化方面，呋喃环上的溴很容易被甲基和羧基取代；使用丁基锂进行锂化，然后分别用碘甲烷和二氧化碳进行处理。
• HASHEM, MD. ABUL;WEYERSTAHL, P.;GREEN, B. S., TETRAHEDRON, 1984, 40, N 1, 203-210
  作者：HASHEM, MD. ABUL、WEYERSTAHL, P.、GREEN, B. S.

  DOI：——

  日期：——
• Synthesis of high enantiomeric purity gem-dihalocyclopropane derivatives from biotransformations of nitriles and amides
  作者：Mei-Xiang Wang、Guo-Qiang Feng、Qi-Yu Zheng

  DOI：10.1016/j.tetasy.2003.11.016

  日期：2004.1

  Enantioselective biotransformations of geminally dihalogenated cyclopropanecarbonitriles and amides are described. Both the reaction rate and enantioselectivity of the nitrile hydratase and amidase involved in Rhodococcus sp. AJ270 microbial cells are strongly governed by the nature of gein-disubstituents on the cyclopropane ring; the amidase generally exhibits steric dependence on the substituents while both the steric and electronic factors of the substituents may affect the action of the nitrile hydratase. The match of steric bulkiness of the substituents at 2- with that at 3-positions on the cyclopropane ring benefits the efficient and highly enantioselective reaction. Coupled with facile chemical transformations, biocatalytic transformations of nitrile and amide supply an effective synthesis of optically active 2,2-disubstitued-3-phenylcyclopropanecarboxylic acid and amide in both enantiomeric forms. (C) 2003 Elsevier Ltd. All rights reserved.