(R)-(E)-4-octen-2-ol | 243863-58-3

• 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)-(E)-4-octen-2-ol
• 英文别名: (R)-4-(E)-octen-3-ol；(E,3R)-oct-4-en-3-ol
• CAS: 243863-58-3
• 化学式: C₈H₁₆O
• 分子量: 128.214
• InChiKey: IWHMIKIFTITXGS-HYDMIIDASA-N

物化性质

• 沸点：
  178.8±8.0 °C(Predicted)
• 密度：
  0.843±0.06 g/cm3(Predicted)

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：

  二碘甲烷 、 (R)-(E)-4-octen-2-ol 在 (4R,5R)-2-butyl-N⁴,N⁴,N⁵,N⁵-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide diethylzinc 作用下， 以 二氯甲烷 为溶剂， 反应 12.17h， 以84%的产率得到(1R,1'S,2'S)-1-(2-propylcyclopropyl)-1-propanol
  参考文献：
  名称：

  使用手性二氧杂硼烷配体的手性烯丙基醇的立体选择性环丙烷化：抗环丙基甲醇衍生物的新途径

  摘要：

  研究了在手性二氧杂硼烷配体1存在下烯丙基醇的非对映选择性环丙烷化反应。当使用2.2当量的双（碘甲基）锌和1.1当量的1时，使用E-烯烃获得了前所未有的高抗选择性。

  DOI：

  10.1016/s0040-4020(99)00448-2
• 作为产物：
  描述：

  辛-4-炔-3-醇 在 lithium aluminium tetrahydride 、 whole lyophilised cells of Rhodococcus ruber DSM 44541 、 丙酮 作用下， 以 phosphate buffer 、 乙醚 为溶剂， 反应 46.0h， 生成 (R)-(E)-4-octen-2-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

• 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.
• The stereoselective cyclopropanation of chiral allylic alcohols using a chiral dioxaborolane ligand: A new route to anti-cyclopropylmethanol derivatives
  作者：AndréB Charette、Hélène Lebel、Alexandre Gagnon

  DOI：10.1016/s0040-4020(99)00448-2

  日期：1999.7

  The diastereoselective cyclopropanation reaction of allylic alcohols in the presence of the chiral dioxaborolane ligand 1 was studied. Unprecedently high anti-selectivities were obtained with E-olefins when 2.2 equivalents of bis(iodomethyl)zinc and 1.1 equivalent of 1 were used.

  研究了在手性二氧杂硼烷配体1存在下烯丙基醇的非对映选择性环丙烷化反应。当使用2.2当量的双（碘甲基）锌和1.1当量的1时，使用E-烯烃获得了前所未有的高抗选择性。