(E)-2-decen-5-ol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-2-decen-5-ol
• 英文别名: (E)-dec-2-en-5-ol
• 化学式: C₁₀H₂₀O
• 分子量: 156.268
• InChiKey: HTVSOGFEYOJMCK-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  反式-巴豆基硼酸频哪醇酯 、 正己醛 在 In(OSO₂CF₃)3 作用下， 以 甲苯 为溶剂， 反应 0.75h， 以70%的产率得到(E)-2-decen-5-ol
  参考文献：
  名称：

  Synthesis of 4-substituted homoallylic alcohols via a one-pot tandem Lewis-acid catalyzed crotylboration-[3,3]-sigmatropic rearrangement

  摘要：

  在催化量的三氟化铟存在下，用E-或Z-克罗丁基硼酸酯对醛进行克罗丁基化反应，得到相应的4-取代的同烯醇。

  DOI：

  10.1039/b418996e

文献信息

• Bismuth mediated barbier synthesis of <i>α</i>-homoallylic alcohols via a sigmatropic rearrangement in [bmim][HSO₄]
  作者：Sucheta Chatterjee、Papiya Dey、Seema V. Kanojia、Subrata Chattopadhyay、Dibakar Goswami

  DOI：10.1080/00397911.2020.1854785

  日期：2021.3.4

  A novel protocol for the Bismuth metal mediated regioselctive crotylation of aldehydes yielding α-homoallylic alcohols has been developed using 20 mol% [bmim][HSO4] as a metal activator, as well as...

  使用 20 mol% [bmim][HSO4] 作为金属活化剂，开发了一种用于铋金属介导的醛类区域选择性巴豆化生成 α-高烯丙醇的新方案，以及...
• Allylbarium Reagents: Unprecedented Regio- and Stereoselective Allylation Reactions of Carbonyl Compounds
  作者：Akira Yanagisawa、Shigeki Habaue、Katsutaka Yasue、Hisashi Yamamoto

  DOI：10.1021/ja00093a010

  日期：1994.7

  The first direct preparation of allylbarium reagents by reaction of insitu generated reactive barium with various allylic chlorides and their new and unexpected selective allylation reactions with carbonyl compounds are disclosed. Highly reactive barium was readily prepared by the reduction of barium iodide with 2 equiv of lithium biphenylide in dry THF at room temperature. A variety of carbonyl compounds reacted with barium reagents generated from (E)- or (Z)-allylic chlorides in THF at -78 degrees C. All reactions resulted in high yields with remarkable alpha-selectivities not only with aldehydes but also with ketones. The double bond geometry of the starting allylic chloride was completely retained in each case. Stereochemically homogeneous (E)- and (Z)beta,gamma-unsaturated carboxylic acids were easily prepared in good yields by highly alpha-selective carboxylation of allylic barium reagents with carbon dioxide. A selective Michael addition reaction with alpha,beta-unsaturated cycloalkanone was also achieved using an allylbarium reagent. Treatment of 2-cyclopentenone (1 equiv) with allylbarium chloride (2 equiv) in THF at -78 degrees C for 20 min afforded 3-allylcyclopentanone in 94% yield with a 1,4/1,2 ratio of >99/1. Furthermore, the in situ generated barium enolate was efficiently trapped with various kinds of electrophiles (Me(2)C=CHCH2Br, (C5H11CHO)-C-n, and CH3COCl).
• Development of a highly α-regioselective indium-mediated allylation reaction in water
  作者：Teck-Peng Loh、Kui-Thong Tan、Jian-Ying Yang、Chao-Li Xiang

  DOI：10.1016/s0040-4039(01)01883-4

  日期：2001.12

  Linear alpha homoallylic alcohol adducts were obtained with high regioselectivities in moderate to good yields using allylic indium reagents in the presence of 10 M water. The exceptionally high regioselectivities observed were neither steric nor electronic in origin from the results presented in this paper. (C) 2001 Elsevier Science Ltd. All rights reserved.
• The First In(OTf)3-Catalyzed Conversion of Kinetically Formed Homoallylic Alcohols into the Thermodynamically Preferred Regioisomers: Application to the Synthesis of 22α-Sterols
  作者：Teck-Peng Loh、Kui-Thong Tan、Qi-Ying Hu

  DOI：10.1002/1521-3773(20010803)40:15<2921::aid-anie2921>3.0.co;2-v

  日期：2001.8.3

  A retro-ene reaction that generates the parent aldehyde and a sigmatropic rearrangement are involved in the In(OTf)3 -catalyzed conversion of homoallylic alcohols 1 into the thermodynamically favored regioisomers 2. This method can be used for the stereocontrolled synthesis of linear homoallylic 22α-sterols from their readily accessible branched 22β isomers.
• US4382869A
  申请人：——

  公开号：US4382869A

  公开（公告）日：1983-05-10