tert-Butyl-((E)-(R)-2-methyl-hex-4-enyloxy)-diphenyl-silane | 144693-94-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: tert-Butyl-((E)-(R)-2-methyl-hex-4-enyloxy)-diphenyl-silane
• 英文别名: tert-butyl-[(E,2R)-2-methylhex-4-enoxy]-diphenylsilane
• CAS: 144693-94-7
• 化学式: C₂₃H₃₂OSi
• 分子量: 352.592
• InChiKey: VQXJIMFPDABSBR-ROUKRRSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  乙醛酸甲酯 、 tert-Butyl-((E)-(R)-2-methyl-hex-4-enyloxy)-diphenyl-silane 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-(2S,3S,6R)-7-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-3,6-dimethyl-hept-4-enoic acid methyl ester 、 (E)-(2R,3R,6R)-7-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-3,6-dimethyl-hept-4-enoic acid methyl ester
  参考文献：
  名称：

  Remote asymmetric induction based on carbonyl-ene reactions with bishomoallylic silyl ethers: dramatic changeover of regioselectivity by the remarkable siloxy effect

  摘要：

  A new approach to remote asymmetric induction is described for not only a 1,4- but also a 1,5-relationship, which is based on the carbonyl-ene reactions with chiral bishomoallylic silyl ethers. Silyl ethers, rather than alkyl ethers, exhibit beta-regiospecificity. Remarkably high levels of remote asymmetric induction can then be established with chiral bishomoallylic ethers to provide eventually a simple and efficient method for asymmetric induction.

  DOI：

  10.1021/jo00049a011