2-undecen-5-yn-4-ol | 207305-91-7

• 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: 2-undecen-5-yn-4-ol
• 英文别名: (E)-undec-2-en-5-yn-4-ol
• CAS: 207305-91-7
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: VZKYHFILDKAZMW-RUDMXATFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-undecen-5-yn-4-ol 生成 (E)-trimethyl(undec-2-en-5-yn-4-yloxy)silane
  参考文献：
  名称：

  Reactivity of 3-silyloxy-1,4-enynes: Gold(III)-catalyzed regioselective nucleophilic substitution

  摘要：

  Gold-catalyzed reactions of 3-silyloxy-1,4-enynes with alcohols afford primary, secondary, and tertiary pent-2-en-4-ynyl ethers in moderate to excellent yields. The substitution proceeds with high regioselectivity. An initial cyclization providing five-membered carbocycles instead was not observed under the reaction conditions. Control experiments show that these reactions are also catalyzed by Bronsted- and Lewis-acids, although scope and yields are markedly reduced. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.09.062
• 作为产物：
  描述：

  巴豆醛 、 1-庚基锂 生成 2-undecen-5-yn-4-ol
  参考文献：
  名称：

  Reactivity of 3-silyloxy-1,4-enynes: Gold(III)-catalyzed regioselective nucleophilic substitution

  摘要：

  Gold-catalyzed reactions of 3-silyloxy-1,4-enynes with alcohols afford primary, secondary, and tertiary pent-2-en-4-ynyl ethers in moderate to excellent yields. The substitution proceeds with high regioselectivity. An initial cyclization providing five-membered carbocycles instead was not observed under the reaction conditions. Control experiments show that these reactions are also catalyzed by Bronsted- and Lewis-acids, although scope and yields are markedly reduced. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.09.062

文献信息

• Substituent effects on the regioselectivity in fluorination of allylic alcohols with DAST
  作者：Abdelghani Boukerb、Danielle Grée、Mohammed Laabassi、René Grée

  DOI：10.1016/s0022-1139(98)00115-8

  日期：1998.2

  The regioselectivity of the fluorination of various allylic and β-dienoic alcohols with DAST has been studied. Substituent effects are important in these reactions; a strong preference for the secondary fluorides versus the primary ones is observed, especially in the case of alkyl and aryl substituted derivatives.

  研究了用DAST氟化各种烯丙基和β-二烯醇的区域选择性。在这些反应中，取代基的作用很重要。观察到仲氟化物相对于伯氟化物的强烈偏爱，特别是在烷基和芳基取代的衍生物的情况下。
• Regiocontrolled synthesis of furans by a mercury(II) catalysed isomerisation of 1-alkynyl-2,3-epoxyalcohols
  作者：Charles M. Marson、Steven Harper、Roger Wrigglesworth

  DOI：10.1039/c39940001879

  日期：——

  2,3,5-Trisubstituted furans are formed by the reaction of 1-alkynyl-2,3-epoxyalcohols with a catalytic amount of mercury(II) prepared from HgO and dilute sulfuric acid.

  2,3,5-三取代呋喃是通过 1-炔基-2,3-环氧醇与催化量的由 HgO 和稀硫酸制备的汞 (II) 反应形成的。
• Synthesis of polysubstituted thiophenes by a catalytic cyclisation of functionalised episulfides
  作者：Charles M. Marson、Jonathan Campbell

  DOI：10.1016/s0040-4039(97)01819-4

  日期：1997.11

  Substituted thiophenes are formed by the reaction of 1-alkynyl-2,3-epithioalcohols with a catalytic amount of mercury(II) prepared from HgO and dilute sulfuric acid. (C) 1997 Elsevier Science Ltd.
• Catalytic Isomerization of 1-Alkynyl-2,3-epoxy Alcohols to Substituted Furans:  Succinct Routes to Furanoid Fatty Acids and Difurylmethanes
  作者：Charles M. Marson、Steven Harper

  DOI：10.1021/jo980856a

  日期：1998.12.1

  A versatile procedure for the preparation of synthetically valuable 2,5-disubstituted and 2,3,5-trisubstituted furans via mercury(II)-mediated isomerization of 1-alkynyl-2,3-epoxy alcohols is described. Mercury(II)-catalyzed isomerization of alkynyl epoxides 3a-k derived from cyclic Phi-alkynyl allylic alcohols furnishes 2,3,5-substituted furans bearing an aldehyde or keto group on the C-2 side chain. The reaction is used in a succinct and efficient synthesis of the furanoid fatty acid F-5. In contrast, the mercury(II)-catalyzed reaction of a series of alkynyl epoxides 3m-p lacking ring fusion affords difurylmethanes 5, presumably by the dimerization of intermediate 2-(alpha-hydroxyalkyl)furans 4.