(+/-)-tridec-1-en-6-yn-4-ol | 215458-27-8

• 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: (+/-)-tridec-1-en-6-yn-4-ol
• 英文别名: Tridec-1-en-6-yn-4-ol
• CAS: 215458-27-8
• 化学式: C₁₃H₂₂O
• 分子量: 194.317
• InChiKey: PSGDZKYEQNZMDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  (+/-)-tridec-1-en-6-yn-4-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 甲苯 为溶剂， 反应 0.08h， 以76%的产率得到(+/-)-3-(1-methyleneheptyl)cyclopent-3-en-1-ol
  参考文献：
  名称：

  Convenient Access to Functionalized Vinylcyclopentenols from Alkynyloxiranes

  摘要：

  beta,gamma-Alkynyl aldehydes, generated in situ by treatment of alkynyloxiranes with a catalytic amount of Sc(OTf)(3) or BF3 center dot OEt2, are effectively trapped by a variety of allyl nucleophiles to afford homopropargylic homoallylic alcohols in good yield and selectivity. Such products are used as substrates for the synthesis of functionalized vinylcyclopentenols via enyne metathesis.

  DOI：

  10.1021/jo062107w
• 作为产物：
  描述：

  (+/-)-oct-1-ynyloxirane 、 四烯丙基锡 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 乙醚 为溶剂， 以71%的产率得到(+/-)-tridec-1-en-6-yn-4-ol
  参考文献：
  名称：

  Convenient Access to Functionalized Vinylcyclopentenols from Alkynyloxiranes

  摘要：

  beta,gamma-Alkynyl aldehydes, generated in situ by treatment of alkynyloxiranes with a catalytic amount of Sc(OTf)(3) or BF3 center dot OEt2, are effectively trapped by a variety of allyl nucleophiles to afford homopropargylic homoallylic alcohols in good yield and selectivity. Such products are used as substrates for the synthesis of functionalized vinylcyclopentenols via enyne metathesis.

  DOI：

  10.1021/jo062107w

文献信息

• Stereocontrolled cyclization of enynols and allenynols with (η2-propene)Ti(O-i-Pr)2. Important role of unprotected hydroxy group at a remote position
  作者：Hirokazu Urabe、Fumie Sato

  DOI：10.1016/s0040-4039(98)01572-x

  日期：1998.10

  Stereochemistry of (eta(2)-propene)Ti(O-i-Pr)(2)-mediated cyclization of enynols and allenynols is efficiently controlled by their remote hydroxy group, showing good diastereaselectivities as high as 82:18-98.5:1.5, which are uniformly superior to those observed for the corresponding t-BuMe2Si ethers. (C) 1998 Elsevier Science Ltd. AII rights reserved.
• Convenient Access to Functionalized Vinylcyclopentenols from Alkynyloxiranes
  作者：Letian Wang、Matthew L. Maddess、Mark Lautens

  DOI：10.1021/jo062107w

  日期：2007.3.1

  beta,gamma-Alkynyl aldehydes, generated in situ by treatment of alkynyloxiranes with a catalytic amount of Sc(OTf)(3) or BF3 center dot OEt2, are effectively trapped by a variety of allyl nucleophiles to afford homopropargylic homoallylic alcohols in good yield and selectivity. Such products are used as substrates for the synthesis of functionalized vinylcyclopentenols via enyne metathesis.