(R)-(E)-2-<<(Benzyloxy)methoxy>methyl>-5-methylhex-3-en-1-ol | 138513-52-7

• 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: (R)-(E)-2-<<(Benzyloxy)methoxy>methyl>-5-methylhex-3-en-1-ol
• 英文别名: (R)-(E)-2-{[(Benzyloxy)methoxy]methyl}-5-methylhex-3-en-1-ol；(E,2R)-5-methyl-2-(phenylmethoxymethoxymethyl)hex-3-en-1-ol
• CAS: 138513-52-7
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: YWUIIZRZWXXSSK-ROJDOSBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  19.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-(E)-2-<<(Benzyloxy)methoxy>methyl>-5-methylhex-3-en-1-ol 在 咪唑 、 sodium tetrahydroborate 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 2-<<(Benzyloxy)methoxy>methyl>-3-<(tert-butyldimethylsilyl)oxy>-1-propanol
  参考文献：
  名称：

  Chemoenzymic preparation of asymmetrized tris(hydroxymethyl)methane (THYM*) and of asymmetrized bis(hydroxymethyl)acetaldehyde (BHYMA*) as new highly versatile chiral building blocks

  摘要：

  A series of asymmetrized tris(hydroxymethyl)methanes 2 and bis(hydroxymethyl)acetaldehydes 3 have been prepared in both enantiomeric forms through a chemoenzymatic methodology. The key step is the highly enantioselective PPL-catalyzed monohydrolysis of 2(E)-alkenyl-1,3-diacetoxypropanes 25-27. A careful study on the effect of unsaturations adjacent to the prochiral center in a series of 2-substituted 1,3-diacetoxypropanes has confirmed the suggested beneficial effect of a pi-system in that position but has also unveiled an unprecedented dramatic effect of double-bond configuration on enantioselectivity. A new empirical model for the interpretation of these and other results, based both on polarity and steric arguments, is proposed. This study provides a general protocol for the efficient synthesis of asymmetrized 1,3-propanediols bearing in position 2 saturated or unsaturated carbon chains.

  DOI：

  10.1021/jo00031a039
• 作为产物：
  描述：

  (E)-1-Acetoxy-2-(acetoxymethyl)-5-methyl-3-hexene 在 氢氧化钾 、 N,N-二异丙基乙胺 作用下， 以 水 、 异丙醇 为溶剂， 反应 7.5h， 生成 (R)-(E)-2-<<(Benzyloxy)methoxy>methyl>-5-methylhex-3-en-1-ol
  参考文献：
  名称：

  Chemoenzymic preparation of asymmetrized tris(hydroxymethyl)methane (THYM*) and of asymmetrized bis(hydroxymethyl)acetaldehyde (BHYMA*) as new highly versatile chiral building blocks

  摘要：

  A series of asymmetrized tris(hydroxymethyl)methanes 2 and bis(hydroxymethyl)acetaldehydes 3 have been prepared in both enantiomeric forms through a chemoenzymatic methodology. The key step is the highly enantioselective PPL-catalyzed monohydrolysis of 2(E)-alkenyl-1,3-diacetoxypropanes 25-27. A careful study on the effect of unsaturations adjacent to the prochiral center in a series of 2-substituted 1,3-diacetoxypropanes has confirmed the suggested beneficial effect of a pi-system in that position but has also unveiled an unprecedented dramatic effect of double-bond configuration on enantioselectivity. A new empirical model for the interpretation of these and other results, based both on polarity and steric arguments, is proposed. This study provides a general protocol for the efficient synthesis of asymmetrized 1,3-propanediols bearing in position 2 saturated or unsaturated carbon chains.

  DOI：

  10.1021/jo00031a039

文献信息

• Asymmetrized trils (hydroxymethyl)methane as a highly stereodivergent chiral building block: preparation of all four stereoisomers of protected 2-hydroxymethyl-1,3-butanediol
  作者：Giuseppe Guanti、Luca Banfi、Enrica Narisano

  DOI：10.1016/s0040-4039(00)97081-3

  日期：1990.1