(+/-)-4-octen-3-ol | 66786-02-5

• 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: (+/-)-4-octen-3-ol
• 英文别名: oct-4-en-3-ol；4-Octen-3-ol
• CAS: 66786-02-5
• 化学式: C₈H₁₆O
• 分子量: 128.214
• InChiKey: IWHMIKIFTITXGS-UHFFFAOYSA-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：

  (+/-)-4-octen-3-ol 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 192.0h， 以39%的产率得到辛-4-烯-3-酮
  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：

  辛-4-炔-3-醇 在 Lindlar's catalyst 喹啉 、 氢气 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以86%的产率得到(+/-)-4-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-free S_NAr-type etherification with allyl alcohols: Synthesis of allyl pyridyl ethers
  作者：Aiwen Huo、Xingzong Wang、Xiang Li、Yan Zhang、Yingjie Guo、Liyan Zhang、Fan Wang、Juhui Wang、Feng Li、Qing He、Hengjie Liang、Tengda Jin、Zhibin Wang、Jingyue Yang

  DOI：10.1080/00397911.2020.1815785

  日期：2020.12.1

  Abstract Allyl pyridyl ethers are important intermediates in organic synthesis, which could be accessed by Williamson or SNAr-type etherification. While Williamson etherification has been well studied, the SNAr-type reaction remains less explored. In this paper, a series of allyl pyridyl ethers were synthesized via transition metal-free SNAr-type etherification with different allyl alcohols in good

  摘要 烯丙基吡啶基醚是有机合成中重要的中间体，可通过Williamson 或SNAr 型醚化反应获得。虽然威廉姆森醚化已经得到很好的研究，但对 SNAr 型反应的探索仍然较少。在本文中，通过无过渡金属的SNAr型醚化与不同的烯丙醇以良好的收率合成了一系列烯丙基吡啶基醚。肉桂醇的低收率醚化最终以分子筛作为添加剂优化到 82% 的收率。图形概要
• Photodeoxygenation of Dibenzothiophene Sulfoxide:  Evidence for a Unimolecular S−O Cleavage Mechanism¹
  作者：Daniel D. Gregory、Zehong Wan、William S. Jenks

  DOI：10.1021/ja962975i

  日期：1997.1.1

  Photolysis of dibenzothiophene sulfoxide results in the formation of dibenzothiophene and oxidized solvent. Though quantum yields are low, chemical yields of the sulfide are quite high. Yields of the oxidized solvents can also be high. Typical products are phenol from benzene, cyclohexanol, and cyclohexene from cyclohexane and 2-cyclohexenol and epoxycyclohexane from cyclohexene. A number of experiments

  二苯并噻吩亚砜的光解导致二苯并噻吩和氧化溶剂的形成。尽管量子产率很低，但硫化物的化学产率却很高。氧化溶剂的产率也可能很高。典型的产品是苯酚、环己醇和环己烯和环己烯的 2-环己烯醇和环氧环己烷。进行了许多旨在阐明羟基化机制的实验，包括测量作为浓度、溶剂、猝灭剂和激发波长函数的量子产率。这些数据与涉及亚砜二聚体的机制不一致，后者也不能正确解释溶剂氧化。建议活性氧化剂可能是原子氧 O(3P) 或密切相关的非共价配合物，
• 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.