(1S,3S)-3-(2,2-Dibromo-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid; compound with 1H-pyrrole | 143123-30-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,3S)-3-(2,2-Dibromo-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid; compound with 1H-pyrrole
• CAS: 143123-30-2
• 化学式: C₄H₅N*2C₈H₁₀Br₂O₂
• 分子量: 663.039
• InChiKey: XVIKUOXRHYGJMS-FINAUTGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  53.09
• 氢给体数：
  2.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  吡咯 、 cis-(1S,3R)-Deltamethrinic acid 以85%的产率得到(1S,3S)-3-(2,2-Dibromo-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid; compound with 1H-pyrrole
  参考文献：
  名称：

  Clathrate formation from 3-(2',2'-dihalovinyl)-2,2-dimethylcyclopropanecarboxylic acid and aromatic compounds: preparation, structure, and application in separation of stereoisomers.

  摘要：

  Clathrate formation was discovered and investigated in a series of stereoisomers of 3-(2',2'-dihalovinyl)-2,2-dimethylcyclopropanecarboxylic acid, 1 (X = Cl, Br). It was found that the equimolar mixture of (1R)-cis and (1S)-cis acids gives rise to crystalline inclusion complexes with simple aromatic compounds such as benzene, fluorobenzene, thiophene, pyrrole, furan, and 2-methylfuran, always in the stoichiometric ratio 1:1:1 with respect to the participating components. No other stereoisomeric mixture of any single enantiomer of the acid 1 forms inclusion complexes. The crystal structure of the inclusion complex obtained from the racemic cis acid 1 (X = Cl) and benzene was determined and compared with that of the neat racemic cis acid. Applicability of the novel inclusion complexes for separation of geometrical (cis vs trans) as well as optical ((1R)-cis or (1S)-cis vs (1RS)-cis) isomers has been demonstrated.

  DOI：

  10.1021/jo00044a016