(1R,4R)-4-Methoxy-3-methylene-1-p-tolyl-pentan-1-ol | 135086-06-5

• 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: (1R,4R)-4-Methoxy-3-methylene-1-p-tolyl-pentan-1-ol
• CAS: 135086-06-5；135086-16-7
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: LWQNJOQNYAOFTI-GXTWGEPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  对甲基苯甲醛 、 Tributyl-(3-methoxy-2-methylene-butyl)-stannane 在 Ti(OiPr)Cl3 作用下， 生成 (1R,4R)-4-Methoxy-3-methylene-1-p-tolyl-pentan-1-ol 、 (1R,4R)-4-Methoxy-3-methylene-1-p-tolyl-pentan-1-ol
  参考文献：
  名称：

  Optically active allylic tin reagent as an enantio-divergent synthon of isoprenoids via remote and divergent asymmetric induction

  摘要：

  (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.

  DOI：

  10.1016/0040-4039(95)00539-o

文献信息

• Divergently stereocontrolled reaction of an allylic silane bearing an asymmetric ethereal carbon toward aldehydes
  作者：Yutaka Nishigaichi、Akio Takuwa、Akifumi Jodai

  DOI：10.1016/s0040-4039(00)79929-1

  日期：1991.5

  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.