3-hydroperoxypent-4-en-2-ol | 212834-85-0

• 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: 3-hydroperoxypent-4-en-2-ol
• CAS: 212834-85-0
• 化学式: C₅H₁₀O₃
• 分子量: 118.133
• InChiKey: TXHNNCYWIPXSFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.41
• 重原子数：
  8.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  3-hydroperoxypent-4-en-2-ol 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 戊-4-烯-2,3-二醇
  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：

  (Z)-pent-3-en-2-ol 在 氧气 、 tetraphenylporphyrin 作用下， 以 四氯化碳 为溶剂， 反应 12.0h， 生成 3-hydroperoxypent-4-en-2-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

• Semisynthetic Enzymes in Asymmetric Synthesis:  Enantioselective Reduction of Racemic Hydroperoxides Catalyzed by Seleno-Subtilisin
  作者：Dietmar Häring、Ellen Schüler、Waldemar Adam、Chantu R. Saha-Möller、Peter Schreier

  DOI：10.1021/jo981665a

  日期：1999.2.1

  The serine protease subtilisin was chemically converted into the peroxidase-active seleno-subtilisin. This semisynthetic enzyme catalyzes the enantioselective reduction of racemic hydroperoxides in the presence of thiophenols to yield optically active hydroperoxides and alcohols on the semipreparative scale. The kinetic parameters and enantioselectivities of seleno-subtilisin-catalyzed reduction of

  将丝氨酸蛋白酶枯草杆菌蛋白酶化学转化为过氧化物酶活性的硒代枯草杆菌蛋白酶。在硫酚的存在下，这种半合成酶催化外消旋氢过氧化物的对映选择性还原，从而以半制备规模生产旋光性氢过氧化物和醇。测定了动力学参数和硒代枯草杆菌蛋白酶催化的各种手性氢过氧化物还原的对映选择性。该半合成酶的催化效率与天然辣根过氧化物酶的催化效率相当。硒代枯草杆菌蛋白酶的对映选择性与先前用于旋光活性氢过氧化物合成的天然酶相反。所以，
• 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%).
• Lipase-catalyzed kinetic resolution of α,β-unsaturated α′-acetoxy ketones
  作者：Waldemar Adam、Marı́a Teresa Dı́az、Chantu R Saha-Möller

  DOI：10.1016/s0957-4166(98)00006-8

  日期：1998.3

  The lipase-catalyzed kinetic resolutions of the alpha,beta-unsaturated alpha'-acetoxy ketones 3a,b have been investigated. Of the lipases examined, CAL-B from Candida antarctica (fraction B) has been shown to be an efficient biocatalyst, which may be used effectively in preparative scale reactions. (C) 1998 Elsevier Science Ltd. All rights reserved.