3-methylene-hex-5-en-1-ol | 42201-29-6

• 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: 3-methylene-hex-5-en-1-ol
• 英文别名: 3-Methylidenehex-5-en-1-ol
• CAS: 42201-29-6
• 化学式: C₇H₁₂O
• 分子量: 112.172
• InChiKey: XAQGISOYQLXFQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  聚合甲醛 、 bromozinc(1+),prop-1-ene 生成 3-methylene-hex-5-en-1-ol
  参考文献：
  名称：

  合成，新结构和有机材料再生产，铝制锌的双反应

  摘要：

  在回流溶剂中加热几个小时后，烯丙基溴化锌形成一种具有双-1,3-有机锌结构的新型有机金属化合物。该化合物与不同的化合物反应，在大多数情况下会导致结构基团的连接：

  DOI：

  10.1016/s0022-328x(00)95144-1

文献信息

• Carboindation of Carbon−Carbon Triple Bonds:  Regioselective Indium-Mediated Allylation of Functionalized Alkynes and Transformation into Halogen-Substituted 1,4-Dienes
  作者：Ernst Klaps、Walther Schmid

  DOI：10.1021/jo9908593

  日期：1999.10.1

  By examining the allylindation of a series of substituted alkynes, the relationships between allylindation reactivity and alkyne structure were systematically investigated. While terminal alkynes with protected hydroxyl groups gave the corresponding allylated branched 1,4-dienes (Markovnikov products) within 5-6 h, the unprotected alkynols reacted markedly faster, requiring only 2-4 h of ultrasonication in THF to produce the 1,4-dienols in good yields. In the latter reactions, the regioisomeric outcome was found to depend on the distance between the hydroxyl group and the alkyne moiety: propargylic substrates gave linear 1,4-dienes (anti-Markovnikov products), suggesting the involvement of bicyclic "chelation-controlled" transition state, while 4-pentynol and higher homologues exclusively afforded the branched 1,4-dienes. Moreover, the proposed vinylic alpha,alpha-bis-indium intermediates from both protected and unprotected substrates were successfully quenched with N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS) to form tri- and tetrasubstituted dienes in good yields. Taken as a whole, these results illustrate the remarkable stability of the allylindium and vinylindium intermediates despite the presence of protic functionalities in the reaction mixture.
• JP2001089465A
  申请人：——

  公开号：JP2001089465A

  公开（公告）日：2001-04-03
• US4165342A
  申请人：——

  公开号：US4165342A

  公开（公告）日：1979-08-21