(Z)-3-octen-2-ol | 69668-89-9

• 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: (Z)-3-octen-2-ol
• 英文别名: 3-Octen-2-ol, (Z)-；(Z)-oct-3-en-2-ol
• CAS: 69668-89-9
• 化学式: C₈H₁₆O
• 分子量: 128.214
• InChiKey: YJJIVDCKSZMHGZ-SREVYHEPSA-N

物化性质

• 沸点：
  88.5-89.5 °C(Press: 26 Torr)
• 密度：
  0.8347 g/cm3(Temp: 21 °C)

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：

  (Z)-3-octen-2-ol 在 氢氧化钾 、 间氯过氧苯甲酸 、 lithium bromide 、 锌 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 8.33h， 生成 (E)-oct-3-en-2-ol
  参考文献：
  名称：

  Corey, L. D.; Singh, S. M.; Oehlschlager, A. C., Canadian Journal of Chemistry, 1987, vol. 65, p. 1821 - 1827

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 、 palladium on activated charcoal 、 Lindlar's catalyst 作用下， 生成 (Z)-3-octen-2-ol
  参考文献：
  名称：

  Heilmann et al., Bulletin de la Societe Chimique de France, 1957, p. 119,122

  摘要：

  DOI：

文献信息

• Hydroxy-directed regio-diastereoselective ene reaction of singlet oxygen with chiral allylic alcohols
  作者：Waldemar Adam、Bernd Nestler

  DOI：10.1021/ja00065a013

  日期：1993.6

  The photooxygenation of chiral allylic alcohols 1a, (Z)-1f-k, ethers 1b-d, and acetate 1e gave the corresponding hydroperoxy homoallylic alcohols and derivatives 2 through the ene reaction with singlet oxygen. While the reaction of the acetate 1e proceeded erythro-diastereoselectively as a result of the classical cis effect, for the allylic alcohols 1a and (Z)-1f-k, in which an alkyl group is located

  手性烯丙醇 1a、(Z)-1f-k、醚 1b-d 和乙酸酯 1e 的光氧化反应通过与单线态氧的烯反应得到相应的氢过氧高烯丙醇和衍生物 2。由于经典的顺式效应，乙酸酯 1e 的反应以赤型非对映选择性进行，对于烯丙醇 1a 和 (Z)-1f-k，其中烷基位于带羟基的取代基的顺式，高观察到threo选择性。这一发现可以通过立体中心的亲核羟基官能团与进入的亲电子单线态氧亲烯体的配位来解释
• Rh-Catalyzed Kinetic Resolution of Enynes and Highly Enantioselective Formation of 4-Alkenyl-2,3-disubstituted Tetrahydrofurans
  作者：Aiwen Lei、Minsheng He、Xumu Zhang

  DOI：10.1021/ja0351950

  日期：2003.9.1

  Rh-catalyzed cycloisomerization of enynes ether with a substituent at the allylic position was examined using (rac)-BINAP, and excellent selectivity was observed. When enantiomerically pure BINAP was used as the ligand, a process that combines kinetic resolution and diastereoselectivity together was developed, in which an enantiomeric product with multiple stereogenic centers was obtained in >99% ee

  使用（外消旋）-BINAP 检查了烯炔醚在烯丙基位置具有取代基的 Rh 催化的环异构化，并观察到了优异的选择性。当使用对映体纯的 BINAP 作为配体时，开发了一种将动力学拆分和非对映选择性相结合的方法，其中通过一步从外消旋起始材料中获得了具有多个立体中心的对映体产品，ee 大于 99%，一半剩余的原料也以 >99% ee 回收。
• Stereo- and regioselectivity in iodo diol formation from acyclic allylic alcohols
  作者：A. Richard Chamberlin、Robert L. Mulholland

  DOI：10.1016/0040-4020(84)80012-5

  日期：1984.1

  with a variety of acyclic allylic alcohols was investigated. Both aqueous iodine and acetylhypoiodite convert certain alkenols into iodo diols and acetoxy iodo alcohols, respectively, with regio- and stereoselectivities as high as 99%. Protection of the alcohol group lowers the selectivity only slightly. Structural factors that control the regioselectivity ofiodohydrin formation in these substrates

  研究了亲电试剂与各种无环烯丙基醇的反应。碘水溶液和乙酰次碘水溶液都将某些烯醇分别转化为碘二醇和乙酰氧基碘醇，其区域和立体选择性高达99％。醇基的保护仅稍微降低了选择性。已经描述了控制这些底物中碘醇形成的区域选择性的结构因素。一些碘代二醇已被脱碘，说明了一个简单的两步程序即可将烯丙基醇转化为苏-1，3-二醇。
• Diastereoselective Catalytic Epoxidation of Chiral Allylic Alcohols by the TS-1 and Ti-β Zeolites:  Evidence for a Hydrogen-Bonded, Peroxy-Type Loaded Complex as Oxidizing Species
  作者：Waldemar Adam、Avelino Corma、T. Indrasena Reddy、Michael Renz

  DOI：10.1021/jo970364i

  日期：1997.5.1

  The similar diastereoselectivities as for peracids implicate a pentacoordinated metal peroxy species in the epoxidation of chiral allylic alcohols by the titanium-containing zeolites TS-1 and Ti-beta. In the loaded complex, the allylic alcohol substrate is fixed through hydrogen bonding to the metal center, with A(1,3) strain as the dominant conformational feature. By comparison of the diastereoselectivities to those for VO(acac)(2)/t-BuOOH, we exclude a peroxy-type complex with direct coordination of the allylic alcohol to the titanium center by means of metal-alcoholate bonding. Neither does a peroxo-type titanium complex apply, as confirmed by comparing the diastereoselectivities with those observed for dioxiranes. With the help of tert-butyl-substituted allylic alcohols as substrates, which are not epoxidized by the TS-1 but by the Ti-beta catalyst, it was unequivocally confirmed that the oxidation occurs inside of the zeolite and not on the outer surface.
• Adam, Waldemar; Kumar, Rajiv; Reddy, T. Indrasena, Angewandte Chemie, 1996, vol. 108, # 8, p. 944 - 947
  作者：Adam, Waldemar、Kumar, Rajiv、Reddy, T. Indrasena、Renz, Michael

  DOI：——

  日期：——