2-(hydroxymethyl)-3-phenyl-2-cyclohexenone | 114908-57-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(hydroxymethyl)-3-phenyl-2-cyclohexenone
• 英文别名: 2-(hydroxymethyl)-5,6-dihydro-[1,1'-biphenyl]-3(4H)-one；2-(hydroxymethyl)-3-phenylcyclohex-2-en-1-one
• CAS: 114908-57-5
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: MKSPIKZTWGGKSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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-phenyl-2-cyclohexenone 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)-3-hydroxy-3,4,5,6-tetrahydro-[1,1'-biphenyl]-3-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 、 水 为溶剂， 反应 0.33h， 生成 2-(hydroxymethyl)-3-phenyl-2-cyclohexenone
  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）。
• Ir‐Catalyzed Cascade Reaction Promotes the Formation of Geometrically Selective Enones from Bis‐allyl Alcohols
  作者：Takaaki Kamishima、Yoshitaka Koseki、Hirotaka Nakatsuji、Sanjay Kumar、Keita Tanita、Hitoshi Kasai

  DOI：10.1002/ejoc.202201002

  日期：2022.11.18

  A cascade reaction including reduction, isomerization, and dehydration provides E-selective or multi-substituted enones from bis-allyl alcohols treated with Crabtree's catalyst. This reaction proceeds smoothly at room temperature under a hydrogen atmosphere.

  包括还原、异构化和脱水的级联反应从用 Crabtree 催化剂处理的双烯丙醇中提供E选择性或多取代的烯酮。该反应在氢气氛下在室温下顺利进行。
• Preparation, reactivity, and spectral properties of 1,3-dioxin vinylogous esters: versatile .beta.-ketovinyl cation equivalents
  作者：Amos B. Smith、Bruce D. Dorsey、Masashi Ohba、Andrew T. Lupo、Michael S. Malamas

  DOI：10.1021/jo00253a024

  日期：1988.9