2-(hydroxymethyl)-3-methylcyclohex-2-en-1-one | 1366469-85-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(hydroxymethyl)-3-methylcyclohex-2-en-1-one
• CAS: 1366469-85-3
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: BEIAVSZUZMOQGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.05
• 重原子数：
  10.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(hydroxymethyl)-3-methylcyclohex-2-en-1-one 在 4-二甲氨基吡啶 、 正丁基锂 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 methyl 3-(2-(((tert-butyldimethylsilyl)oxy)methyl)-1-hydroxy-3-methylcyclohex-2-en-1-yl)propiolate
  参考文献：
  名称：

  Syntheses of structurally-simplified and fluorescently-labeled neovibsanin derivatives and analysis of their neurite outgrowth activity in PC12 cells

  摘要：

  The syntheses of several neovibsanin derivatives were carried out in order to elucidate the simple structure required for displaying neurite outgrowth activity. In addition, a fluorescent probe molecule was synthesized and the analysis of its behavior in the PC12 cell line showed that the neovibsanins accumulate on the outer edge of the cell at the site of formation of prominences. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.006
• 作为产物：
  描述：

  4,6,7,8-tetrahydro-5H-1,3-benzodioxin-5-one 在 盐酸 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.33h， 生成 2-(hydroxymethyl)-3-methylcyclohex-2-en-1-one
  参考文献：
  名称：

  Syntheses of structurally-simplified and fluorescently-labeled neovibsanin derivatives and analysis of their neurite outgrowth activity in PC12 cells

  摘要：

  The syntheses of several neovibsanin derivatives were carried out in order to elucidate the simple structure required for displaying neurite outgrowth activity. In addition, a fluorescent probe molecule was synthesized and the analysis of its behavior in the PC12 cell line showed that the neovibsanins accumulate on the outer edge of the cell at the site of formation of prominences. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.006

文献信息

• Anionic Diels–Alder Chemistry of Cyclic Sodium Dien-1-olates Delivering Highly Stereoselective and Functionalized Polycyclic Adducts
  作者：Jing-Kai Huang、Kak-Shan Shia

  DOI：10.1021/acs.orglett.1c01807

  日期：2021.8.6

  Anionic Diels–Alder chemistry of electron-deficient cross-conjugated vinylogous alkenones, providing highly stable sodium dienolate ion pairs as electron-rich dienes in the presence of a weak sodium base in THF, has been newly developed, leading to a single Diels–Alder adduct, in racemic form, in moderate to high yields (up to 97%, 37 examples).

  新开发的缺电子交叉共轭乙烯基烯酮的阴离子 Diels-Alder 化学，在 THF 中存在弱钠碱的情况下，提供高度稳定的二烯醇钠离子对作为富电子二烯，导致单个 Diels-Alder加合物，外消旋形式，中等至高产率（高达 97%，37 个实例）。
• Asymmetric Formal Nucleophilic <i>o</i>-Cresolylation with Morita–Baylis–Hillman Carbonates of 2-Cyclohexenones via Palladium Catalysis
  作者：Xue Song、Jie Zhang、Yu-Xing Wu、Qin Ouyang、Wei Du、Ying-Chun Chen

  DOI：10.1021/jacs.2c04101

  日期：2022.6.8

  from 2-cyclohexanones and diverse aldehydes under palladium catalysis, by in situ generation of electron-neutral and HOMO-raised η2-Pd(0)-dienone complexes via an oxidative insertion/π–σ-isomerization/β-H elimination activation sequence. The subsequent umpolung vinylogous addition to a variety of imines is realized upon Pd(0)-mediated π-Lewis base catalysis, finally furnishing o-cresolylated products

  在这里，我们报告了在钯催化下与 MOrita- Baylis -Hillman (MBH) 碳酸酯在钯催化下的不对称形式亲核亲核化反应，通过原位产生电子中性和 HOMO 引发的 η 2 -Pd( 0)-二烯酮复合物通过氧化插入/π-σ-异构化/β-H消除激活序列。随后在 Pd(0) 介导的 π-Lewis 碱催化下实现了对各种亚胺的 umpolung 插烯加成，最终提供了o-甲酚化产物，然后是另一个级联的 π-σ-异构化/β-H 消除/芳构化过程。通过采用新设计的庞大的手性亚膦酰胺配体，对大量的底物组装实现了中等至优异的非对映和对映选择性，并且可以轻松地加工所得的多功能产品以获取多种对映体富集的结构。此外，催化反应途径通过对照实验得到了很好的启发。