(R)-oct-7-yn-2-ol | 81077-15-8

• 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: (R)-oct-7-yn-2-ol
• 英文别名: (R)-1-oktyn-7-ol；(2R)-oct-7-yn-2-ol
• CAS: 81077-15-8
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: YAUCGNOJRISZRH-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  (R)-oct-7-yn-2-ol 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 14.5h， 生成 methyl (1R,4R,11S,14R)-13-bromo-14-hydroxy-4-methyl-2-oxo-3-oxabicyclo[9.4.0]pentadec-12-en-9-yne-11-carboxylate
  参考文献：
  名称：

  Highly Diastereoselective Type-I IMDA Reaction Forming Medium-Sized Macrolactones

  摘要：

  Intramolecular Diels-Alder (IMDA) reactions of 2-pyrones containing an alkyne tether occur with remarkably high diastereofacial selectivity to provide medium-sized macrolactones. Because of the strain in the alkyne-tethered macrocyclic system, a single methyl group in the tether provides sufficient conformational bias to generate medium-sized macrocycles with unusually high selectivity.

  DOI：

  10.1021/ol061198g
• 作为产物：
  描述：

  (R)-oct-4-yn-2-ol 在 potassium hydride 、 1,3-丙二胺 作用下， 反应 2.0h， 以83%的产率得到(R)-oct-7-yn-2-ol
  参考文献：
  名称：

  Highly Diastereoselective Type-I IMDA Reaction Forming Medium-Sized Macrolactones

  摘要：

  Intramolecular Diels-Alder (IMDA) reactions of 2-pyrones containing an alkyne tether occur with remarkably high diastereofacial selectivity to provide medium-sized macrolactones. Because of the strain in the alkyne-tethered macrocyclic system, a single methyl group in the tether provides sufficient conformational bias to generate medium-sized macrocycles with unusually high selectivity.

  DOI：

  10.1021/ol061198g

文献信息

• The isomerization of optically-active propargyl alcohols to terminal acetylenes.
  作者：M.Mark Midland、Ronald L. Halterman、Charles A. Brown、Angela Yamaichi

  DOI：10.1016/s0040-4039(01)82095-5

  日期：——

  The isomerization of optically-active secondary propargyl alcohols, RCHOHCC(CH2)nCH3, to terminal acetylenic alcohols, RCHOH(CH2)n+1 C=CH, by potassium 3-aminopropylamide (KAPA) proceeds without loss of configuration at the hydroxy center.

  3-氨基丙基酰胺钾（KAPA）将光学活性仲炔丙醇RCHOHCC（CH 2）n CH 3异构化为末端炔醇RCHOH（CH 2）n + 1C= CH在羟基中心的构型。
• Highly Diastereoselective Type-I IMDA Reaction Forming Medium-Sized Macrolactones
  作者：Jeong-Taek Shin、Sung-Cho Hong、Seunghoon Shin、Cheon-Gyu Cho

  DOI：10.1021/ol061198g

  日期：2006.7.1

  Intramolecular Diels-Alder (IMDA) reactions of 2-pyrones containing an alkyne tether occur with remarkably high diastereofacial selectivity to provide medium-sized macrolactones. Because of the strain in the alkyne-tethered macrocyclic system, a single methyl group in the tether provides sufficient conformational bias to generate medium-sized macrocycles with unusually high selectivity.