(4S,5S)-4-Bromo-5-hydroxy-cyclohexane-1,2-dicarboxylic acid dimethyl ester | 77743-51-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5S)-4-Bromo-5-hydroxy-cyclohexane-1,2-dicarboxylic acid dimethyl ester
• CAS: 77743-51-2
• 化学式: C₁₀H₁₅BrO₅
• 分子量: 295.13
• InChiKey: SSKPTOYSKCGYMU-JAFIHTMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.48
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  CIS-4-环己烯-1,2-二甲酸二甲酯 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 为溶剂， 以50%的产率得到dimethyl (1S,2R)-4,5-dibromocyclohexane-1,2-dicarboxylate
  参考文献：
  名称：

  Micellar effects on alkene bromination. 2. The role of alkene hydrophobicity

  摘要：

  Surface polarity of cetyltrimethylammonium bromide (CTAB) aqueous micelles was checked by use of as a probe the bromination reaction of a series of 1-alkenes and a water-soluble alkene, cis-4-cyclohexene-1,2-dicarboxylic acid dimethyl ester (I). There was strong inhibition (10(5)-10(6)-fold) of the second-order reaction rate constants relative to those in water; moreover, both kinetics and the product distributions suggested that alkenes had different locations at the micellar surface. Kinetics in the presence of added NaBr and n-decane supported this location hypothesis.

  DOI：

  10.1021/jo00009a019