(R)-non-4-en-3-ol | 167817-94-9

• 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: (R)-non-4-en-3-ol
• 英文别名: (E,3R)-non-4-en-3-ol
• CAS: 167817-94-9
• 化学式: C₉H₁₈O
• 分子量: 142.241
• InChiKey: FXQKOHVMBAZJDX-FCZSHJHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  乙酰氯 、 (R)-non-4-en-3-ol 在 sodium hydride 作用下， 生成 Acetic acid (E)-(R)-1-ethyl-hept-2-enyl ester
  参考文献：
  名称：

  Steric and Electronic Effects in Conformational Preferences of C1-Oxygenated Chiral Alkenes

  摘要：

  A variable temperature NMR study shows that the benzyl protective group on the hydroxy function of a chiral allylic alcohol enhances the CH eclipsed form (I). On the other hand, various silyl ethers enhance the preference for the CO eclipsed conformer. However, when both the allylic R group and the hydroxy protective group are bulky (R tert-butyl, P = TIPS), the staggered conformation of the chiral alkene becomes preferred. An acetate group does not have an apparent effect on the conformational preference of the protected allylic alcohol. These facts are explained in terms of steric and electronic interactions.

  DOI：

  10.1021/jo00112a012
• 作为产物：
  描述：

  1-己炔 在 diethylzinc 、 (2R)-(+)-3-exo-N-morpholinoisoborneol 作用下， 以 正己烷 为溶剂， 反应 2.5h， 生成 (R)-non-4-en-3-ol
  参考文献：
  名称：

  通过双乙烯基化-环氧双氧合反应一锅不对称合成无环手性环氧醇

  摘要：

  我们已经开发了一种一锅法，可以从简单的非手性起始原料中不对称合成具有挑战性的一类酰基仲环氧醇，具有三个连续的立体中心。通过醛的串联催化不对称乙烯基化和非对映选择性环氧化反应来合成环氧醇。在锌催化剂的存在下，将原位生成的乙烯基锌试剂经历对映选择性加成到醛中，以提供烯丙基锌醇盐。然后通过添加双氧和酒石酸钛催化剂将这种物质环氧化，从而在大多数情况下提供具有优异对映选择性的环氧醇，并且非对映选择性高达4.5：1，有利于苏式-非对映异构体。本文所述的系统代表了合成效率和选择性方面的重大进步。

  DOI：

  10.1021/jo048345d

文献信息

• Processes for Highly Enantio- and Diastereoselective Synthesis of Acyclic Epoxy Alcohols and Allylic Epoxy Alcohols
  申请人：Walsh Patrick

  公开号：US20090163728A1

  公开（公告）日：2009-06-25

  The inventive subject matter relates to novel processes for making an epoxy alcohol from an aldehyde, comprising the steps of: (a) adding (i) an organozinc compound or (ii) divinylzinc compound and an diorganozinc compound to said aldehyde in the presence of a first catalyst to form an allylic alkoxide compound; and (b) epoxidizing said allylic alkoxide compound in the presence of an oxidant and a second catalyst.

  本发明涉及一种从醛制备环氧醇的新工艺，包括以下步骤：(a)在第一催化剂的存在下向所述醛中加入(i)有机锌化合物或(ii)二乙烯基锌化合物和二有机锌化合物，以形成烯丙氧化物化合物；(b)在氧化剂和第二催化剂的存在下使烯丙氧化物化合物环氧化。
• Conformational study of chiral alkenes: the influence of protective groups on the relative stability of ground-state rotational isomers
  作者：Benjamin W. Gung、Mark A. Wolf

  DOI：10.1021/jo00077a023

  日期：1993.12

  A variable temperature NMR study shows that a protective group on the hydroxy function of a chiral allylic alcohol can either enhance or counter the influence of the vinyl substituent on the ground-state (GS) conformations. If the allylic hydroxy is protected as a methyl ether, the CH-eclipsed form I becomes favored to a greater degree for normal chiral alkenes. Furthermore, conformer I becomes preferred even for the gamma-hydroxy-alpha,beta-unsaturated esters, which normally favor the CO-eclipsed form (II). On the other hand, the tert-butyldimethylsilyl (TBDMS) ether enhances the preference for conformer II for the gamma-hydroxy-alpha,beta-unsaturated esters and diminishes the preference for the CH-eclipsed form of normal chiral alkenes. These facts are explained by the size of the allylic oxygen lone pairs.
• US8236976B2
  申请人：——

  公开号：US8236976B2

  公开（公告）日：2012-08-07
• One-Pot Asymmetric Synthesis of Acyclic Chiral Epoxy Alcohols via Tandem Vinylation−Epoxidation with Dioxygen
  作者：Alice E. Lurain、Patrick J. Carroll、Patrick J. Walsh

  DOI：10.1021/jo048345d

  日期：2005.2.1

  the asymmetric synthesis of a synthetically challenging class of acylic secondary epoxy alcohols with three contiguous stereocenters from simple achiral starting materials. The epoxy alcohols are synthesized via a tandem catalytic asymmetric vinylation of an aldehyde coupled with a diastereoselective epoxidation reaction. A vinylzinc reagent generated in situ undergoes enantioselective addition to an

  我们已经开发了一种一锅法，可以从简单的非手性起始原料中不对称合成具有挑战性的一类酰基仲环氧醇，具有三个连续的立体中心。通过醛的串联催化不对称乙烯基化和非对映选择性环氧化反应来合成环氧醇。在锌催化剂的存在下，将原位生成的乙烯基锌试剂经历对映选择性加成到醛中，以提供烯丙基锌醇盐。然后通过添加双氧和酒石酸钛催化剂将这种物质环氧化，从而在大多数情况下提供具有优异对映选择性的环氧醇，并且非对映选择性高达4.5：1，有利于苏式-非对映异构体。本文所述的系统代表了合成效率和选择性方面的重大进步。
• Steric and Electronic Effects in Conformational Preferences of C1-Oxygenated Chiral Alkenes
  作者：Benjamin W. Gung、Jason P. Melnick、Mark A. Wolf、Amanda King

  DOI：10.1021/jo00112a012

  日期：1995.4

  A variable temperature NMR study shows that the benzyl protective group on the hydroxy function of a chiral allylic alcohol enhances the CH eclipsed form (I). On the other hand, various silyl ethers enhance the preference for the CO eclipsed conformer. However, when both the allylic R group and the hydroxy protective group are bulky (R tert-butyl, P = TIPS), the staggered conformation of the chiral alkene becomes preferred. An acetate group does not have an apparent effect on the conformational preference of the protected allylic alcohol. These facts are explained in terms of steric and electronic interactions.