(+/-)-5-(E)-octen-3-ol | 71097-18-2

• 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: (+/-)-5-(E)-octen-3-ol
• 英文别名: rac-(E)-5-octen-3-ol；oct-5t-en-3-ol；Oct-5-en-3-ol；(E)-oct-5-en-3-ol
• CAS: 71097-18-2
• 化学式: C₈H₁₆O
• 分子量: 128.214
• InChiKey: UGRZKHOGKYSHQP-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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：

  (+/-)-5-(E)-octen-3-ol 在 whole lyophilised cells of Rhodococcus ruber DSM 44541 、 丙酮 作用下， 以 phosphate buffer 为溶剂， 反应 20.0h， 生成 (E)-oct-5-en-3-one 、 (R)-5-(E)-octen-3-ol 、 (S)-5-(E)-octen-3-ol
  参考文献：
  名称：

  Biocatalytic oxidative kinetic resolution of sec-alcohols: stereocontrol through substrate-modification

  摘要：

  Whole lyophilised cells of Rhodococcus ruber DSM 44541 were employed for the oxidative kinetic resolution of sec-alcohols using acetone as hydrogen acceptor. The enantioselectivity of this process could be controlled effectively by introducing C-C multiple bonds into substrates, which were inefficiently recognised, in particular short-chain (omega-1)-alcohols and (omega-2)-analogs. Thus, the enantioselectivities of rac-2-pentanol (E= 16.8) and rac-3-octanol (E= 13.3) were significantly improved by introducing a C=C bond adjacent to the alcohol moiety to give racemic (E)-pent-3-en-2-ol and 4-(E)-octen-3-ol, which were resolved with excellent selectivities (E >100 and 50, respectively). In addition, it was found that high stereodifferentiation between the E- and Z-configured double bonds occurred, as the corresponding (Z)-isomers were not converted. Similar selectivity-enhancing effects were observed with acetylenic analogs. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00795-4
• 作为产物：
  描述：

  5-辛炔-3-醇 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以83%的产率得到(+/-)-5-(E)-octen-3-ol
  参考文献：
  名称：

  Biocatalytic oxidative kinetic resolution of sec-alcohols: stereocontrol through substrate-modification

  摘要：

  Whole lyophilised cells of Rhodococcus ruber DSM 44541 were employed for the oxidative kinetic resolution of sec-alcohols using acetone as hydrogen acceptor. The enantioselectivity of this process could be controlled effectively by introducing C-C multiple bonds into substrates, which were inefficiently recognised, in particular short-chain (omega-1)-alcohols and (omega-2)-analogs. Thus, the enantioselectivities of rac-2-pentanol (E= 16.8) and rac-3-octanol (E= 13.3) were significantly improved by introducing a C=C bond adjacent to the alcohol moiety to give racemic (E)-pent-3-en-2-ol and 4-(E)-octen-3-ol, which were resolved with excellent selectivities (E >100 and 50, respectively). In addition, it was found that high stereodifferentiation between the E- and Z-configured double bonds occurred, as the corresponding (Z)-isomers were not converted. Similar selectivity-enhancing effects were observed with acetylenic analogs. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00795-4

文献信息

• Transition metal promoted alkylations of unsaturated alcohols. Alkylation of alkynols with organoalanes promoted by Group IVA metal-cyclopentadienyl compounds
  作者：David C. Brown、Stephen A. Nichols、A. Bruce Gilpin、David W. Thompson

  DOI：10.1021/jo01334a002

  日期：1979.9
• BROWN D. C.; NICHOLS S. A.; GILPIN A. B.; THOMPSON D. W., J. ORG. CHEM., 1979, 44, NO 20, 3457-3461
  作者：BROWN D. C.、 NICHOLS S. A.、 GILPIN A. B.、 THOMPSON D. W.

  DOI：——

  日期：——
• Biocatalytic oxidative kinetic resolution of sec-alcohols: stereocontrol through substrate-modification
  作者：Wolfgang Stampfer、Birgit Kosjek、Kurt Faber、Wolfgang Kroutil

  DOI：10.1016/s0957-4166(02)00795-4

  日期：2003.1

  Whole lyophilised cells of Rhodococcus ruber DSM 44541 were employed for the oxidative kinetic resolution of sec-alcohols using acetone as hydrogen acceptor. The enantioselectivity of this process could be controlled effectively by introducing C-C multiple bonds into substrates, which were inefficiently recognised, in particular short-chain (omega-1)-alcohols and (omega-2)-analogs. Thus, the enantioselectivities of rac-2-pentanol (E= 16.8) and rac-3-octanol (E= 13.3) were significantly improved by introducing a C=C bond adjacent to the alcohol moiety to give racemic (E)-pent-3-en-2-ol and 4-(E)-octen-3-ol, which were resolved with excellent selectivities (E >100 and 50, respectively). In addition, it was found that high stereodifferentiation between the E- and Z-configured double bonds occurred, as the corresponding (Z)-isomers were not converted. Similar selectivity-enhancing effects were observed with acetylenic analogs. (C) 2003 Elsevier Science Ltd. All rights reserved.