(2S,5S)-2-Methoxy-3-methylene-dodecan-5-ol | 135086-07-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,5S)-2-Methoxy-3-methylene-dodecan-5-ol
• CAS: 135086-07-6；135086-17-8
• 化学式: C₁₄H₂₈O₂
• 分子量: 228.375
• InChiKey: GFFBSHUZYMCXPR-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  16.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  正辛醛 、 (3-Methoxy-2-methylene-butyl)-trimethyl-silane 在 乙醚 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以94%的产率得到(2S,5S)-2-Methoxy-3-methylene-dodecan-5-ol
  参考文献：
  名称：

  Divergently stereocontrolled reaction of an allylic silane bearing an asymmetric ethereal carbon toward aldehydes

  摘要：

  Lewis acid mediated allylation of aldehydes by an allylsilane bearing an asymmetric ethereal functionality proceeded in divergently stereocontrolled manners, i.e., TiCl4 afforded the syn isomer, whereas BF3.OEt2 afforded the anti isomer predominantly.

  DOI：

  10.1016/s0040-4039(00)79929-1

文献信息

• Optically active allylic tin reagent as an enantio-divergent synthon of isoprenoids via remote and divergent asymmetric induction
  作者：Yutaka Nishigaichi、Hiroki Kuramoto、Akio Takuwa

  DOI：10.1016/0040-4039(95)00539-o

  日期：1995.5

  (S)-2-(1-Hydroxymethyl)allyltin (1a) can be prepared in high enantiomeric purity. When its methylated and acetylated derivatives are allowed to add to aldehydes with the help of i-PrOTiCl3 and SnCl4, syn- and anti-homoallylic alcohols are stereoselectively obtained, respectively, via 1,4-asymmetric induction. These reactions are applied to the synthesis of the both enantiomers of a pheromone constituent, ipsenol, from a single enantiomer of 1a.