(4S)-4-hydroxyheptanoic acid | 44911-93-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (4S)-4-hydroxyheptanoic acid
• CAS: 44911-93-5
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: MYCCAWPBMVOJQF-LURJTMIESA-N

物化性质

• 沸点：
  292.3±23.0 °C(Predicted)
• 密度：
  1.070±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S)-4-hydroxyheptanoic acid 在 盐酸 作用下， 生成 (5S)-二氢-5-丙基-2(3H)-呋喃酮
  参考文献：
  名称：

  Enzymatic resolution of racemic lactones

  摘要：

  DOI：

  10.1016/s0040-4039(00)82077-8
• 作为产物：
  描述：

  (4S)-1-庚烯-4-醇 在 chromium(VI) oxide 、 4-二甲氨基吡啶 、 sodium hydroxide 、 chloroborane methyl sulfide complex 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 (4S)-4-hydroxyheptanoic acid
  参考文献：
  名称：

  Chiral Synthesis via Organoboranes. 39. A Facile Synthesis of .gamma.-Substituted-.gamma.-butyrolactones in Exceptionally High Enantiomeric Purity

  摘要：

  Optically active homoallylic alcohols of exceptionally high enantiomeric purity (98-greater than or equal to 99 % ee) readily available via asymmetric allylboration were converted into p-nitrobenzoate esters and subjected to hydroboration followed by oxidation with CrO3 in aqueous acetic acid (10% H2O) to obtain the corresponding carboxylic acids with the same number of carbon atoms. The protecting ester group was hydrolyzed and the product lactonized in situ to the gamma-substituted gamma-butyrolactones 5 (R = Me, Pr, i-Pr, t-Bu, Ph, (E)-CH=CHCH3) usually without racemization and in good yields. The method is convenient and potentially valuable for. the synthesis of highly functionalized gamma-butyrolactones in high optical purity.

  DOI：

  10.1021/jo00081a014

文献信息

• Enzymatic resolution of racemic lactones
  作者：L. Blanco、E. Guibé-Jampel、G. Rousseau

  DOI：10.1016/s0040-4039(00)82077-8

  日期：1988.1
• JPH06165695A
  申请人：——

  公开号：JPH06165695A

  公开（公告）日：1994-06-14
• Chiral Synthesis via Organoboranes. 39. A Facile Synthesis of .gamma.-Substituted-.gamma.-butyrolactones in Exceptionally High Enantiomeric Purity
  作者：Herbert C. Brown、Shekhar V. Kulkarni、Uday S. Racherla

  DOI：10.1021/jo00081a014

  日期：1994.1

  Optically active homoallylic alcohols of exceptionally high enantiomeric purity (98-greater than or equal to 99 % ee) readily available via asymmetric allylboration were converted into p-nitrobenzoate esters and subjected to hydroboration followed by oxidation with CrO3 in aqueous acetic acid (10% H2O) to obtain the corresponding carboxylic acids with the same number of carbon atoms. The protecting ester group was hydrolyzed and the product lactonized in situ to the gamma-substituted gamma-butyrolactones 5 (R = Me, Pr, i-Pr, t-Bu, Ph, (E)-CH=CHCH3) usually without racemization and in good yields. The method is convenient and potentially valuable for. the synthesis of highly functionalized gamma-butyrolactones in high optical purity.