5-methyl-1-hexene-3,4-diol | 716378-16-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-methyl-1-hexene-3,4-diol
• 英文别名: 5-Methylhex-1-ene-3,4-diol；5-methylhex-1-ene-3,4-diol
• CAS: 716378-16-4
• 化学式: C₇H₁₄O₂
• 分子量: 130.187
• InChiKey: WTRPIFJNKQUEEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methyl-1-hexene-3,4-diol 在 甲醇 、 4-二甲氨基吡啶 、 phosphate buffer 、 lipase CAL-B 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 128.0h， 生成 Acetic acid (1R,2R)-2-hydroxy-3-methyl-1-vinyl-butyl ester
  参考文献：
  名称：

  Lipase-catalyzed kinetic resolution of threo -configured 1,2-diols: a comparative study of transesterification versus hydrolysis

  摘要：

  The kinetic resolution of the alpha,beta-unsaturated vicinal diols 3 has been investigated by irreversible transesterification in organic media and by hydrolysis of the corresponding diacetates 6 (Scheme 1). The best results were obtained in the hydrolysis of the diacetates with the lipase CAL-B from Candida antarctica as a catalyst. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00043-3
• 作为产物：
  描述：

  反式-2-甲基-4-己烯-3-醇 在 氧气 、 tetraphenylporphyrin 、 三苯基膦 作用下， 以 四氯化碳 为溶剂， 生成 5-methyl-1-hexene-3,4-diol
  参考文献：
  名称：

  Synthesis of vinyl 1,2-diketones

  摘要：

  A new route is outlined for preparation of vinyl 1,2-diketones via a three-step sequence. First, allylic alcohols are photooxidized by O-2 to hydroperoxides, which are reduced to vinyl 1,2-diols. These vinyl 1,2-diols are oxidized to vinyl 1,2-diketones with oxoammonium salts, which are prepared in situ from organic nitroxyl radicals. The new route is short, avoids the use of protecting groups, and is generally applicable to obtain aliphatic or aromatic vinyl 1,2-diketones. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2004.03.157

文献信息

• Synthesis of vinyl 1,2-diketones
  作者：Lothar W. Habel、Sigrid De Keersmaecker、Joos Wahlen、Pierre A. Jacobs、Dirk E. De Vos

  DOI：10.1016/j.tetlet.2004.03.157

  日期：2004.5

  A new route is outlined for preparation of vinyl 1,2-diketones via a three-step sequence. First, allylic alcohols are photooxidized by O-2 to hydroperoxides, which are reduced to vinyl 1,2-diols. These vinyl 1,2-diols are oxidized to vinyl 1,2-diketones with oxoammonium salts, which are prepared in situ from organic nitroxyl radicals. The new route is short, avoids the use of protecting groups, and is generally applicable to obtain aliphatic or aromatic vinyl 1,2-diketones. (C) 2004 Published by Elsevier Ltd.
• Lipase-catalyzed kinetic resolution of threo -configured 1,2-diols: a comparative study of transesterification versus hydrolysis
  作者：Waldemar Adam、Marı́a Teresa Dı́az、Chantu R. Saha-Möller

  DOI：10.1016/s0957-4166(98)00043-3

  日期：1998.2

  The kinetic resolution of the alpha,beta-unsaturated vicinal diols 3 has been investigated by irreversible transesterification in organic media and by hydrolysis of the corresponding diacetates 6 (Scheme 1). The best results were obtained in the hydrolysis of the diacetates with the lipase CAL-B from Candida antarctica as a catalyst. (C) 1998 Elsevier Science Ltd. All rights reserved.