(1S,3S)-2,2-dibromo-3-phenylcyclopropanecarboxylic acid | 1205-31-8

• 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: (1S,3S)-2,2-dibromo-3-phenylcyclopropanecarboxylic acid
• 英文别名: 2,2-Dibrom-3t-phenyl-cyclopropan-1r-carbonsaeure；(1S,2S)-2,2-dibromo-3-phenylcyclopropanecarboxylic acid；(1S,3S)-2,2-dibromo-3-phenylcyclopropane-1-carboxylic acid
• CAS: 1205-31-8
• 化学式: C₁₀H₈Br₂O₂
• 分子量: 319.98
• InChiKey: ZRYYLFBAOCSPMW-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：

  (1S,3S)-2,2-dibromo-3-phenylcyclopropanecarboxylic acid 在 silver(II) oxide 、 溴 作用下， 以 二氯甲烷 为溶剂， 反应 25.17h， 生成 (2S,3R)-1,1,2-tribromo-3-phenylcyclopropane 、 (2R,3R)-1,1,2-tribromo-3-phenylcyclopropane
  参考文献：
  名称：

  Stereo- and regiocontrol in ene-dimerisation and trimerisation of 1-trimethylsilyl-3-phenylcyclopropene

  摘要：

  1-Trimethylsilyl-3-phenylcyclopropene and its 2D-analog undergo a highly stereocontrolled ene-reaction to give a single dinner. Further reaction leads to one or more trimers derived through two ene-reactions. The dinner formed easily undergoes cycloaddition with active dienes and nitrile oxides while the trimers do not react under the same conditions. The first enantioselective example of an ene-reaction of cyclopropene derivatives using optically active 1-trimethylsilyl-3S-phenylcyclopropene is also discussed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.077
• 作为产物：
  描述：

  trans-2,2-dibromo-3-phenylcyclopropylcarbaldehyde 在 potassium phosphate buffer 、 Rhodococcus sp. AJ₂₇₀ cells 作用下， 反应 144.0h， 生成 2,2-dibromo-3-phenylcyclopropanecarboxylic acid 、 (1S,3S)-2,2-dibromo-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

• Stereo- and regiocontrol in ene-dimerisation and trimerisation of 1-trimethylsilyl-3-phenylcyclopropene
  作者：Andrey E. Sheshenev、Mark S. Baird、Ivan G. Bolesov、Alexandre S. Shashkov

  DOI：10.1016/j.tet.2009.10.077

  日期：2009.12

  1-Trimethylsilyl-3-phenylcyclopropene and its 2D-analog undergo a highly stereocontrolled ene-reaction to give a single dinner. Further reaction leads to one or more trimers derived through two ene-reactions. The dinner formed easily undergoes cycloaddition with active dienes and nitrile oxides while the trimers do not react under the same conditions. The first enantioselective example of an ene-reaction of cyclopropene derivatives using optically active 1-trimethylsilyl-3S-phenylcyclopropene is also discussed. (C) 2009 Elsevier Ltd. All rights reserved.
• 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.