(R)-(-)-5-hydroxyoctanol | 149071-04-5

• 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)-(-)-5-hydroxyoctanol
• 英文别名: (R)-octane-1,5-diol；(R)-1,5-octanediol；(5R)-octane-1,5-diol
• CAS: 149071-04-5
• 化学式: C₈H₁₈O₂
• 分子量: 146.23
• InChiKey: ZKRNQSNKDPEUOH-MRVPVSSYSA-N

物化性质

• 沸点：
  256.0±8.0 °C(Predicted)
• 密度：
  0.937±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-(-)-5-hydroxyoctanol 在 三乙烯二胺 、 氢氧化钾 、 二乙胺基三氟化硫 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (S)-(-)-5-fluorooctanol
  参考文献：
  名称：

  Optical Resolution of 5-Alkyl-δ-Valerolactones and Synthesis of Optically Active 5-Fluoroalkanols

  摘要：

  Optical resolutions of 5-alkyl-delta-valerolactones were carried out by derivatization to the diastereomeric amides, in which (R)-(+)1-(1-naphthyl)ethylamine or (S)-(-)-1-phenylethylamine were used as resolving agents. Optically active 5-fluoroalkanols, useful intermediates for fluorinated ferroelectric liquid crystals, were derived from the resolved lactones in four steps without racemization.

  DOI：

  10.1080/10242430210707
• 作为产物：
  描述：

  (R)-(+)-5-propyl-δ-valerolactone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-(-)-5-hydroxyoctanol
  参考文献：
  名称：

  Optical Resolution of 5-Alkyl-δ-Valerolactones and Synthesis of Optically Active 5-Fluoroalkanols

  摘要：

  Optical resolutions of 5-alkyl-delta-valerolactones were carried out by derivatization to the diastereomeric amides, in which (R)-(+)1-(1-naphthyl)ethylamine or (S)-(-)-1-phenylethylamine were used as resolving agents. Optically active 5-fluoroalkanols, useful intermediates for fluorinated ferroelectric liquid crystals, were derived from the resolved lactones in four steps without racemization.

  DOI：

  10.1080/10242430210707

文献信息

• Remote Ester Group Leads to Efficient Kinetic Resolution of Racemic Aliphatic Alcohols via Asymmetric Hydrogenation
  作者：Xiao-Hui Yang、Ke Wang、Shou-Fei Zhu、Jian-Hua Xie、Qi-Lin Zhou

  DOI：10.1021/ja510990v

  日期：2014.12.17

  A highly efficient method for kinetic resolution of racemic aliphatic alcohols without conversion of the hydroxyl group has been realized; the method involves hydrogenation mediated by a remote ester group and is catalyzed by a chiral iridium complex. This powerful, environmentally friendly method provides chiral δ-alkyl-δ-hydroxy esters and δ-alkyl-1,5-diols in good yields with high enantioselectivities

  实现了一种无需羟基转化即可动力学拆分外消旋脂肪醇的高效方法；该方法涉及由远程酯基介导的氢化，并由手性铱络合物催化。即使在极低的催化剂负载量（0.001 mol%）下，这种强大、环保的方法也能以良好的收率和高对映选择性提供手性 δ-烷基-δ-羟基酯和 δ-烷基-1,5-二醇。
• Enantiospecific synthesis of N-benzyl-2-alkyl pyrrolidines and piperidines mediated by chiral organoborane reagents
  作者：Tom Nguyen、Dan Sherman、David Ball、Michael Solow、Bakthan Singaram

  DOI：10.1016/s0957-4166(00)82334-4

  日期：1993.2

  A new general method for synthesizing N-benzyl-2-alkylpyrrolidines and N-benzyl-2-alkylpiperidines, having very high enantiomeric excess, has been achieved starting from aldehydes and organoborane reagents.