5-Methyl-2-methylene-hex-4-enal | 249621-16-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Methyl-2-methylene-hex-4-enal
• 英文别名: 5-Methyl-2-methylidenehex-4-enal；5-methyl-2-methylidenehex-4-enal
• CAS: 249621-16-7
• 化学式: C₈H₁₂O
• 分子量: 124.183
• InChiKey: DUUHRVFUBWSKJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-Methyl-2-methylene-hex-4-enal 在 baker's yeast 、 氯化铵 、 蔗糖 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 4-己烯-1-醇,2,5-二甲基-,(2S)-
  参考文献：
  名称：

  Baker's yeast mediated biohydrogenation of unsaturated compounds containing a methylene group: enantioselective preparation of 2-methyl alkanols from 2-substituted acrolein acetals

  摘要：

  The baker's yeast mediated biohydrogenation of unsaturated compounds containing a methylene group may constitute an enantioselective biocatalytic approach to the preparation of 2-methyl-1-alkanols, as exemplified by the reduction of the compounds 8a-d to 90-98% enantiomerically pure alcohols 2a-d. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00256-6
• 作为产物：
  描述：

  5-methyl-2-methylenehex-4-en-1-ol 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 反应 16.0h， 生成 5-Methyl-2-methylene-hex-4-enal
  参考文献：
  名称：

  Baker's yeast mediated biohydrogenation of unsaturated compounds containing a methylene group: enantioselective preparation of 2-methyl alkanols from 2-substituted acrolein acetals

  摘要：

  The baker's yeast mediated biohydrogenation of unsaturated compounds containing a methylene group may constitute an enantioselective biocatalytic approach to the preparation of 2-methyl-1-alkanols, as exemplified by the reduction of the compounds 8a-d to 90-98% enantiomerically pure alcohols 2a-d. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00256-6

文献信息

• Synthesis of Chiral Tertiary Boronic Esters by Oxime-Directed Catalytic Asymmetric Hydroboration
  作者：Veronika M. Shoba、Nathan C. Thacker、Andrew J. Bochat、James M. Takacs

  DOI：10.1002/anie.201509137

  日期：2016.1.22

  now report that the oxime‐directed CAHB of alkyl‐substituted methylidene and trisubstituted alkene substrates by pinacolborane (pinBH) affords oxime‐containing chiral tertiary boronic esters with yields up to 87 % and enantiomeric ratios up to 96:4 e.r. The utility of the method is demonstrated by the formation of chiral diols and O‐substituted hydroxylamines, the generation of quaternary carbon stereocenters

  手性硼酸酯是不对称合成中有用的中间体。先前我们已经表明，羰基定向催化不对称硼氢化（CAHB）是一种合成功能化伯和仲手性硼酸酯的有效方法。我们现在报告称，频哪醇硼烷（pinBH）的由肟取代的烷基取代的亚甲基和三取代的烯烃底物的CAHB可提供含肟的手性叔硼酸酯，其收率高达87％，对映体比率高达96：4。通过形成手性二醇和O-取代的羟胺，通过碳-碳偶联反应生成季碳立构中心，以及制备手性的3,4,4-三取代的异恶唑啉，证明了该方法的有效性。
• Baker's yeast mediated biohydrogenation of unsaturated compounds containing a methylene group: enantioselective preparation of 2-methyl alkanols from 2-substituted acrolein acetals
  作者：Patrizia Ferraboschi、Shahrzad Reza-Elahi、Elisa Verza、Enzo Santaniello

  DOI：10.1016/s0957-4166(99)00256-6

  日期：1999.7

  The baker's yeast mediated biohydrogenation of unsaturated compounds containing a methylene group may constitute an enantioselective biocatalytic approach to the preparation of 2-methyl-1-alkanols, as exemplified by the reduction of the compounds 8a-d to 90-98% enantiomerically pure alcohols 2a-d. (C) 1999 Elsevier Science Ltd. All rights reserved.