4-Hydroperoxy-2-methyl-hex-5-en-3-ol

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氢过氧化物
• 英文名称: 4-Hydroperoxy-2-methyl-hex-5-en-3-ol
• 英文别名: 4-hydroperoxy-2-methylhex-5-en-3-ol
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: ADTOFPQGCFCJKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.05
• 重原子数：
  10.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-Hydroperoxy-2-methyl-hex-5-en-3-ol 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 5-methyl-1-hexene-3,4-diol
  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：

  (2Z)-5-methylhex-2-en-4-ol 在 氧气 、 tetraphenylporphyrin 作用下， 以 四氯化碳 为溶剂， 反应 12.0h， 生成 4-Hydroperoxy-2-methyl-hex-5-en-3-ol
  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

文献信息

• Horseradish Peroxidase-Catalyzed Enantioselective Reduction of Racemic Hydroperoxy Homoallylic Alcohols:  A Novel Enzymatic Method for the Preparation of Optically Active, Unsaturated Diols and Hydroperoxy Alcohols
  作者：Waldemar Adam、Michael Lazarus、Ute Hoch、Marion N. Korb、Chantu R. Saha-Möller、Peter Schreier

  DOI：10.1021/jo980028h

  日期：1998.9.1

  The kinetic resolution of chiral diastereomeric hydroperoxy homoallylic alcohols 1 by horseradish peroxidase-catalyzed asymmetric reduction affords the optically active (R,R) or (R,S) allylic diols 2 and (S,S) or (S,R) hydroperoxy homoallylic alcohols 1 in high enantiomeric excess (up to 99%).

  辣根过氧化物酶催化的不对称还原动力学拆分手性非对映体氢过氧均丙醇1，提供光学活性（R，R）或（R，S）烯丙基二醇2和（S，S）或（S，R）氢过氧均丙醇高对映体过量（高达99％）中为1。
• Optically Active Epoxy Diols by Titanium-Catalyzed Oxidation of Enantiomerically Enriched Hydroperoxy and Hydroxy Homoallylic Alcohols
  作者：Waldemar Adam、Marion N. Korb、Chantu R. Saha-Möller

  DOI：10.1002/(sici)1099-0690(199805)1998:5<907::aid-ejoc907>3.0.co;2-f

  日期：1998.5

  The Ti-catalyzed epoxidation of optically active (S,S)-hydroperoxy homoallylic alcohols 2 affords the epoxy diol (S,R,S)-4 in high diastereoselectivity (d.r. up to 95:5), while the optically active hydroxy homoallylic alcohols (R,R)-3 are epoxidized by the β-hydroperoxy alcohol 5 under titanium catalysis to the corresponding epoxy (R,S,R)-diol 4 in a diastereomeric ratio up to > 99:1. This high diastereoselectivity

  光学活性 (S,S)-氢过氧高烯丙醇 2 的 Ti 催化环氧化以高非对映选择性（dr 高达 95:5）提供环氧二醇 (S,R,S)-4，而光学活性羟基高烯丙醇(R,R)-3 在钛催化下被 β-氢过氧醇 5 环氧化成相应的环氧 (R,S,R)-二醇 4，非对映体比例高达 > 99:1。这种高非对映选择性在氧转移的刚性模板方面被合理化，其中氢过氧醇 2 或 5 三齿连接，二醇 3 双齿结合到钛金属。通过这些氧化途径，可以方便地获得两种对映体环氧二醇4。
• Horseradish peroxidase (HRP)-catalysed enantioselective reduction of racemic hydroperoxy homoallylic alcohols: a novel enzymatic method for the preparation of optically active, unsaturated diols and hydroperoxy alcohols
  作者：Waldemar Adam、Ute Hoch、Hans-Ulrich Humpf、Chantu R. Saha-Möller、Peter Schreier

  DOI：10.1039/cc9960002701

  日期：——

  The kinetic resolution of chiral diastereoisomeric hydroperoxy homoallylic alcohols by horseradish peroxidase (HRP)-catalysed asymmetric reduction affords the optically active (R,R) or (R,S) allylic diols and (S,S) or (S,R) hydroperoxy homoallylic alcohols in high enantiomeric excess (up to 99%).