(R)-hex-5-yn-2-ol | 129234-95-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-hex-5-yn-2-ol
• 英文别名: (R)-5-hexyn-2-ol；(2R)-hex-5-yn-2-ol
• CAS: 129234-95-3
• 化学式: C₆H₁₀O
• 分子量: 98.1448
• InChiKey: FZUOCMXBAJIQHD-ZCFIWIBFSA-N

物化性质

• 沸点：
  152.0±0.0 °C(Predicted)
• 密度：
  0.898±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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)-hex-5-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 16.0h， 生成 (1S,6R,9R,11R)-15-Bromo-6-methyl-7,12-dioxa-tricyclo[9.2.2.0^1,9]pentadec-14-en-2-yne-8,13-dione
  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：

  (+/-)-5-hexyn-2-ol 生成 (R)-hex-5-yn-2-ol
  参考文献：
  名称：

  Combined microbial oxidation and reduction: a new approach to the highyield synthesis of homochiral unsaturated secondary alcohols from racemates

  摘要：

  The oxidation of racemic secondary alcohols with Bacillus stearothermophilus followed by reduction of the mixture with Yarrowia lipolytica to afford high yields of the enantiomerically pure R-alcohols la,b,d is described. Comparisons with Yarrowia lipolytica reduction, Bacillus stearothermophilus oxidation, and the contemporary use of the two microrganisms have been made.

  DOI：

  10.1016/0957-4166(95)00402-5

文献信息

• Combined microbial oxidation and reduction: a new approach to the highyield synthesis of homochiral unsaturated secondary alcohols from racemates
  作者：Giancarlo Fantin、Marco Fogagnolo、Pier Paolo Giovannini、Alessandro Medici、Paola Pedrini

  DOI：10.1016/0957-4166(95)00402-5

  日期：1995.12

  The oxidation of racemic secondary alcohols with Bacillus stearothermophilus followed by reduction of the mixture with Yarrowia lipolytica to afford high yields of the enantiomerically pure R-alcohols la,b,d is described. Comparisons with Yarrowia lipolytica reduction, Bacillus stearothermophilus oxidation, and the contemporary use of the two microrganisms have been made.
• 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.