2-methyl-1-octen-4-ol | 153254-13-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-1-octen-4-ol
• 英文别名: 2-methyloct-1-en-4-ol
• CAS: 153254-13-8；400710-06-7
• 化学式: C₉H₁₈O
• 分子量: 142.241
• InChiKey: ALKKTTNAUMZYIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：

  2-methyl-1-octen-4-ol 在 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以63%的产率得到4-羟基辛烷-2-酮
  参考文献：
  名称：

  贝克酵母还原 β-羟基酮

  摘要：

  研究了面包酵母将 β-羟基酮还原为相应的 1,3-二醇，以开发同时控制多个立体中心构型的方法。发现这些反应是对映特异性的，并且通常以良好的非对映选择性为特征。还考虑了在 α 位置的碳原子上具有取代基的底物。当α-碳原子上的取代基是环的一部分时，观察到更高的选择性。

  DOI：

  10.1002/ejoc.200901006
• 作为产物：
  描述：

  正戊醛 、 甲基烯丙基溴化镁 以 四氢呋喃 为溶剂， 反应 4.0h， 以50%的产率得到2-methyl-1-octen-4-ol
  参考文献：
  名称：

  Synthesis of Alkyl-Substituted Six-Membered Lactones through Ring-Closing Metathesis of Homoallyl Acrylates. An Easy Route to Pyran-2-ones, Constituents of Tobacco Flavor

  摘要：

  The ring-closing metathesis (RCM) reactions of homoallylic acrylates bearing alkyl substituents on various positions of their skeleton afford the corresponding pentenolides in the presence of carbene ruthenium catalysts. For R-3 = R-4 = H, or R-3 = Me, R-4 = H, the reactions are catalyzed by complex [RuCl2(PCy3)(2)(CHPh)], while a second-generation Grubbs catalyst is required when R-3 = H and R-4 = Me, R-3 = R-4 = Me, or R-3 = i-Pr and R-4 = H. Alkyl substitution at the homoallylic carbon (R-1, R-2) increases the yield of the reaction when both the acrylic and/or homoallylic double bonds are methyl-substituted. The interaction of the catalyst with the substrate in the initiation stage involves the homoallylic double bond rather than the acrylic moiety, and the resulting alkylidene species from the first-generation Grubbs catalyst can be observed by H-1 and P-31 NMR. The racemic tobacco constituents 4-isopropyl-5,6-dihydropyran-2-one and 4-isopropyltetrahydropyran-2-one are prepared via a short reaction sequence, involving the RCM reaction as the key transformation.

  DOI：

  10.1021/jo070600h

文献信息

• Stabilisierung von Chlorfluoralkanen
  申请人：Kali-Chemie Aktiengesellschaft

  公开号：EP0306861A2

  公开（公告）日：1989-03-15

  Verwendung von But-3-en-1-ol-Verbindungen zur Stabilisie­rung von Zusammensetzungen, die Chlorfluoralkane neben Aminen, Aminoalkoholen und aminbasischen Polyolen enthalten.

  使用丁-3-烯-1-醇化合物来稳定含有氯氟烃以及胺、氨基醇和以胺为基础的多元醇的成分。
• Stereoselective Cyclization Reactions of IBX-Generated Alkoxyamidyl Radicals
  作者：Birgit Janza、Armido Studer

  DOI：10.1021/jo0509399

  日期：2005.8.1

  [GRAPHICS]In this paper, a method for the generation of alkoxyamidyl radicals is presented. These N-centered radicals can efficiently be formed starting from the corresponding acylated alkoxyamines using IBX as an oxidant. Stereoselective 5-exo and 6-exo reactions with these N-heteroatom-centered radicals leading to isoxazolidines and [1,2]oxazinanes are discussed. The N-O bond in the heterocycles can readily be cleaved with SmI2 to provide N-acylated 1,3-amino alcohols.
• ROMPgel supported allylboronate: a purification-free method for the preparation of homoallylic alcohols
  作者：Thomas Arnauld、Anthony G.M Barrett、Robert Seifried

  DOI：10.1016/s0040-4039(01)01667-7

  日期：2001.10

  Allylboration of various aldehydes was carried out by a ROMPgel supported allylboronate. Filtration and evaporation gave the corresponding homoallylic alcohols in high yield and purity (>95%). (C) 2001 Elsevier Science Ltd. All rights reserved.
• US4883913A
  申请人：——

  公开号：US4883913A

  公开（公告）日：1989-11-28
• Synthesis of Alkyl-Substituted Six-Membered Lactones through Ring-Closing Metathesis of Homoallyl Acrylates. An Easy Route to Pyran-2-ones, Constituents of Tobacco Flavor
  作者：Andrea D'Annibale、Laura Ciaralli、Mauro Bassetti、Chiara Pasquini

  DOI：10.1021/jo070600h

  日期：2007.8.1

  The ring-closing metathesis (RCM) reactions of homoallylic acrylates bearing alkyl substituents on various positions of their skeleton afford the corresponding pentenolides in the presence of carbene ruthenium catalysts. For R-3 = R-4 = H, or R-3 = Me, R-4 = H, the reactions are catalyzed by complex [RuCl2(PCy3)(2)(CHPh)], while a second-generation Grubbs catalyst is required when R-3 = H and R-4 = Me, R-3 = R-4 = Me, or R-3 = i-Pr and R-4 = H. Alkyl substitution at the homoallylic carbon (R-1, R-2) increases the yield of the reaction when both the acrylic and/or homoallylic double bonds are methyl-substituted. The interaction of the catalyst with the substrate in the initiation stage involves the homoallylic double bond rather than the acrylic moiety, and the resulting alkylidene species from the first-generation Grubbs catalyst can be observed by H-1 and P-31 NMR. The racemic tobacco constituents 4-isopropyl-5,6-dihydropyran-2-one and 4-isopropyltetrahydropyran-2-one are prepared via a short reaction sequence, involving the RCM reaction as the key transformation.