2-methyl-2-nonen-1-ol | 91008-40-1

• 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: 2-methyl-2-nonen-1-ol
• 英文别名: 2-methyl-non-2-en-1-ol；2-Nonen-1-ol, 2-methyl-, (E)-；2-methylnon-2-en-1-ol
• CAS: 91008-40-1
• 化学式: C₁₀H₂₀O
• 分子量: 156.268
• InChiKey: QQYNAKSGWRFPOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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-2-nonen-1-ol 生成 (+/-)-(2R,3R)-2,3-epoxy-2-methyl-1-nonanol
  参考文献：
  名称：

  Stereoselective Synthesis of Highly Substituted .gamma.-Lactones and Butenolides by Intramolecular Michael Addition of Enantiomerically Enriched .gamma.-[(Phenylthio)acyl]oxy .alpha.,.beta.-Unsaturated Esters

  摘要：

  The synthesis of polysubstituted gamma-lactones by the base-induced cyclization of enantiomerically enriched gamma-((phenylthio)acyl)oxy alpha,beta-unsaturated esters obtained from 2,3-epoxy alcohols is described. The procedure is highly stereoselective and compatible with a wide range of functionalities (ester, tetrahydropyranyl ether, silyl ether, etc.). Varying degrees of substitution, including quaternary centers, in the final gamma-lactone were synthesized with excellent stereoselectivity. Useful functional interconversions were successfully demonstrated, in particular those resulting in butenolides. By the use of AM1 it was concluded that the intramolecular Michael reaction can be described as a kinetically controlled reaction in which the relative stability of the transition states for all possible final configurations led to geometries in agreement with the experimental results.

  DOI：

  10.1021/jo00095a022
• 作为产物：
  描述：

  4-<(1-hexyl-2-methylprop-2-enyl)sulphonyl>toluene 生成 2-methyl-2-nonen-1-ol
  参考文献：
  名称：

  由β-γ-环氧砜合成烯丙醇

  摘要：

  DOI：

  10.1016/s0040-4039(01)93527-0

文献信息

• Solid Phase Synthesis of Globomycin and SF-1902 A₅
  作者：Francisco Sarabia、Samy Chammaa、Cristina García-Ruiz

  DOI：10.1021/jo1025145

  日期：2011.4.1

  peptidic fragment and a new asymmetric methodology of epoxidation for the preparation of the lipidic chain. The linkage between both fragments was successfully achieved in solid phase to complete the syntheses via a macrolactonization reaction executed prior to the cleavage of the acyclic precursors from the solid support. These syntheses provide access to the rapid generation of a library of analogues

  报道了天然脂环二肽类抗生素球霉素和SF-1902 A 5的合成，利用固相技术构建了肽片段，并采用了一种新的不对称环氧化方法来制备脂​​质链。两个片段之间的键合在固相中成功完成，通过在从固体载体上裂解无环前体之前进行的大环内酯化反应完成了合成。这些合成物通过修饰氨基酸残基和脂质链提供了快速生成类似物文库的途径，从而基于对酶信号肽酶II的抑制，促进了具有有趣作用机制的新抗生素的鉴定。
• Stereoselective Synthesis of Highly Substituted .gamma.-Lactones and Butenolides by Intramolecular Michael Addition of Enantiomerically Enriched .gamma.-[(Phenylthio)acyl]oxy .alpha.,.beta.-Unsaturated Esters
  作者：Carmen M. Rodriguez、Tomas Martin、Miguel A. Ramirez、Victor S. Martin

  DOI：10.1021/jo00095a022

  日期：1994.8

  The synthesis of polysubstituted gamma-lactones by the base-induced cyclization of enantiomerically enriched gamma-((phenylthio)acyl)oxy alpha,beta-unsaturated esters obtained from 2,3-epoxy alcohols is described. The procedure is highly stereoselective and compatible with a wide range of functionalities (ester, tetrahydropyranyl ether, silyl ether, etc.). Varying degrees of substitution, including quaternary centers, in the final gamma-lactone were synthesized with excellent stereoselectivity. Useful functional interconversions were successfully demonstrated, in particular those resulting in butenolides. By the use of AM1 it was concluded that the intramolecular Michael reaction can be described as a kinetically controlled reaction in which the relative stability of the transition states for all possible final configurations led to geometries in agreement with the experimental results.
• A synthesis of allylic alcohols from β-γ-epoxysulfones
  作者：Philip J. Kocienski

  DOI：10.1016/s0040-4039(01)93527-0

  日期：1979.1