[(2S,3S)-3-[(3S)-3-bromo-4-hydroxy-4-methylpentyl]-3-methyloxiran-2-yl]methyl 4-nitrobenzoate | 146204-96-8

• 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: [(2S,3S)-3-[(3S)-3-bromo-4-hydroxy-4-methylpentyl]-3-methyloxiran-2-yl]methyl 4-nitrobenzoate
• CAS: 146204-96-8
• 化学式: C₁₇H₂₂BrNO₆
• 分子量: 416.269
• InChiKey: JGRLRUHLRBSQAD-ZQIUZPCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2S,3S)-3-[(3S)-3-bromo-4-hydroxy-4-methylpentyl]-3-methyloxiran-2-yl]methyl 4-nitrobenzoate 在 sodium hydroxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 {(2S,3S)-3-[2-((R)-3,3-Dimethyl-oxiranyl)-ethyl]-3-methyl-oxiranyl}-methanol
  参考文献：
  名称：

  Synthesis of four stereoisomers of the higher dipteran juvenile hormone III bisepoxide

  摘要：

  The 6S,7S,10R-, 6S,7S,10S-, 6R,7R,10S- and 6R,7R,10R-stereoisomers of the juvenile hormone III bisepoxide from higher Dipteran insects have been synthesised in high stereoisomeric purity. The route involves Sharpless epoxidation of geraniol to enantiomeric epoxyalcohols, which are each elaborated via separable diastereomeric bromohydrins.

  DOI：

  10.1016/s0040-4039(00)74741-1
• 作为产物：
  描述：

  香叶醇 在 titanium(IV) isopropylate 叔丁基过氧化氢 、 N-溴代丁二酰亚胺(NBS) 、 水 、 (+)-Weinsaeure-diethylester 、 三乙胺 作用下， 生成 [(2S,3S)-3-[(3S)-3-bromo-4-hydroxy-4-methylpentyl]-3-methyloxiran-2-yl]methyl 4-nitrobenzoate
  参考文献：
  名称：

  Synthesis of four stereoisomers of the higher dipteran juvenile hormone III bisepoxide

  摘要：

  The 6S,7S,10R-, 6S,7S,10S-, 6R,7R,10S- and 6R,7R,10R-stereoisomers of the juvenile hormone III bisepoxide from higher Dipteran insects have been synthesised in high stereoisomeric purity. The route involves Sharpless epoxidation of geraniol to enantiomeric epoxyalcohols, which are each elaborated via separable diastereomeric bromohydrins.

  DOI：

  10.1016/s0040-4039(00)74741-1

文献信息

• Synthesis of four stereoisomers of the higher dipteran juvenile hormone III bisepoxide
  作者：Rodney W. Rickards、Richard D. Thomas

  DOI：10.1016/s0040-4039(00)74741-1

  日期：1992.12

  The 6S,7S,10R-, 6S,7S,10S-, 6R,7R,10S- and 6R,7R,10R-stereoisomers of the juvenile hormone III bisepoxide from higher Dipteran insects have been synthesised in high stereoisomeric purity. The route involves Sharpless epoxidation of geraniol to enantiomeric epoxyalcohols, which are each elaborated via separable diastereomeric bromohydrins.