(Z)-(S)-2-(Acetoxymethyl)hept-3-en-1-ol | 138760-89-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-(S)-2-(Acetoxymethyl)hept-3-en-1-ol
• 英文别名: (S)-2-(acetoxymethyl)-3(Z)-hepten-1-ol；[(Z,2S)-2-(hydroxymethyl)hept-3-enyl] acetate
• CAS: 138760-89-1
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: HPMOPQAAAVILCC-OMMCCPJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.51
• 重原子数：
  13.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (Z)-(S)-2-(Acetoxymethyl)hept-3-en-1-ol 在 咪唑 、 叔丁基过氧化氢 、 氢氧化钾 、 bis(acetylacetonate)oxovanadium 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (S)-3-Benzyloxy-2-((2S,3R)-3-propyl-oxiranyl)-propan-1-ol
  参考文献：
  名称：

  Stereoselective epoxidation of asymmetrized 2-alkenyl-1,3-propanediols.

  摘要：

  Asymmetrized 2-alkenyl 1,3-propanediols are stereoselectively epoxidized to the same main diastereoisomer both with 3-chloroperbenzoic acid and the VO(acac)2/t-butyl hydroperoxyde system. Using the latter epoxidating reagent in combination with a protection-deprotection sequence involving the two homoallylic hydroxy groups, all the four cis epoxides were easily achieved in stereoisomeric pure form starting from a single common (Z) precursor.

  DOI：

  10.1016/0040-4039(91)80450-k
• 作为产物：
  描述：

  1,3-二乙酰氧基丙酮 在 palladium, 5% on calcium carbonate, poisoned with lead 2,6-二甲基吡啶 、 正丁基锂 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 7.5h， 生成 (Z)-(S)-2-(Acetoxymethyl)hept-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

• Stereodivergent Synthesis of cis epoxides derived from asymmetrized 2-alkenyl-1,3-propanediols
  作者：Giuseppe Guanti、Luca Banfi、Valeria Merlo、Enrica Narisano、Sergio Thea

  DOI：10.1016/s0040-4020(01)80220-9

  日期：——

  Cis epoxides of any desired absolute stereochemistry have been obtained in a high enantio- and diastereodivergent manner via diastereospecific epoxidation of asymmetrized (Z)-2-alkenyl-1,3-propanediols, in turn obtained through a chemoenzymatic route, and a protection-deprotection ‘trick’ on hydroxy groups.

  通过不对称的（Z）-2-烯基-1,3-丙二醇的非对映特异性环氧化，以高对映异构和非对映异构的方式获得了任何所需的绝对立体化学的顺式环氧化物，进而通过化学酶促途径和保护-脱保护得到了在羟基上“欺骗”。