(R)-1-(9H-fluoren-9-yloxy)propan-2-ol | 1369852-93-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (R)-1-(9H-fluoren-9-yloxy)propan-2-ol
• 英文别名: (2R)-1-(9H-fluoren-9-yloxy)propan-2-ol
• CAS: 1369852-93-6
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: MHXOZEWLNUFMCR-LLVKDONJSA-N

物化性质

• 沸点：
  413.6±40.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-1-(9H-fluoren-9-yloxy)propan-2-ol 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以80%的产率得到(R)-1,2-丙二醇
  参考文献：
  名称：

  Mono-etherification of racemic propane-1,2-diol by a tin(II) bromide catalyzed reaction with diazofluorene and a study of the Pseudomonas cepacia lipase catalyzed acetylation of the mono-ethers

  摘要：

  The tin(II) bromide catalyzed reaction of diazofluorene with racemic propane-1,2-diol in 1,2-dimethoxymethane gave the 1- and 2-monoethers in similar amounts. After tritylation of the 2-ether, 2-(9H-fluoren-9-yloxy)-1-triphenylmethyloxypropane and 1-(9H-fluoren-9-yloxy)propan-2-ol were obtained in pure form. The enantiomeric 1-fluorenyl ethers were resolved by kinetic resolution by transacetylation with the help of Pseudomonas cepacia lipase and both enantiomers of the propane-1,2-diol were obtained after deprotection. The racemic 2-(9H-fluoren-9-yloxy)propan-1-ol was obtained after de-triphenylmethylation. However, transacetylation onto this alcohol under identical conditions to those used for the 1-fluorenyl ether showed no enantioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.01.013
• 作为产物：
  描述：

  (R)-2-acetoxy-1-(9H-fluoren-9-yloxy)propane 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以100%的产率得到(R)-1-(9H-fluoren-9-yloxy)propan-2-ol
  参考文献：
  名称：

  Mono-etherification of racemic propane-1,2-diol by a tin(II) bromide catalyzed reaction with diazofluorene and a study of the Pseudomonas cepacia lipase catalyzed acetylation of the mono-ethers

  摘要：

  The tin(II) bromide catalyzed reaction of diazofluorene with racemic propane-1,2-diol in 1,2-dimethoxymethane gave the 1- and 2-monoethers in similar amounts. After tritylation of the 2-ether, 2-(9H-fluoren-9-yloxy)-1-triphenylmethyloxypropane and 1-(9H-fluoren-9-yloxy)propan-2-ol were obtained in pure form. The enantiomeric 1-fluorenyl ethers were resolved by kinetic resolution by transacetylation with the help of Pseudomonas cepacia lipase and both enantiomers of the propane-1,2-diol were obtained after deprotection. The racemic 2-(9H-fluoren-9-yloxy)propan-1-ol was obtained after de-triphenylmethylation. However, transacetylation onto this alcohol under identical conditions to those used for the 1-fluorenyl ether showed no enantioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.01.013

文献信息

• Mono-etherification of racemic propane-1,2-diol by a tin(II) bromide catalyzed reaction with diazofluorene and a study of the Pseudomonas cepacia lipase catalyzed acetylation of the mono-ethers
  作者：Sigthor Petursson、Sigridur Jonsdottir

  DOI：10.1016/j.tetasy.2012.01.013

  日期：2012.1

  The tin(II) bromide catalyzed reaction of diazofluorene with racemic propane-1,2-diol in 1,2-dimethoxymethane gave the 1- and 2-monoethers in similar amounts. After tritylation of the 2-ether, 2-(9H-fluoren-9-yloxy)-1-triphenylmethyloxypropane and 1-(9H-fluoren-9-yloxy)propan-2-ol were obtained in pure form. The enantiomeric 1-fluorenyl ethers were resolved by kinetic resolution by transacetylation with the help of Pseudomonas cepacia lipase and both enantiomers of the propane-1,2-diol were obtained after deprotection. The racemic 2-(9H-fluoren-9-yloxy)propan-1-ol was obtained after de-triphenylmethylation. However, transacetylation onto this alcohol under identical conditions to those used for the 1-fluorenyl ether showed no enantioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.