6-羟基-4,4-二甲基环己-2-烯-1-酮 | 42117-27-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 6-羟基-4,4-二甲基环己-2-烯-1-酮
• 英文名称: 6-hydroxy-4,4-dimethylcyclohex-2-ene-1-one
• 英文别名: 6-Hydroxy-4,4-dimethylcyclohex-2-en-1-one
• CAS: 42117-27-1
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: FKWQACMGUFRZGS-UHFFFAOYSA-N

物化性质

• 沸点：
  241.8±40.0 °C(Predicted)
• 密度：
  1.064±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  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
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-羟基-4,4-二甲基环己-2-烯-1-酮 在 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 trans-2-acetoxy-4,4,5-trimethylcyclohexanone
  参考文献：
  名称：

  Functional group hybrids. Reactivity of .alpha.'-nucleofuge .alpha.,.beta.-unsaturated ketones. 1. Reactions with organocopper reagents

  摘要：

  A series of alpha-nucleofuge alpha',beta'-unsaturated ketones encompassing a variety of structural types and nucleofuges was prepared. Treatment of these compounds with lithium dimethylcuprate or methylcopper leads primarily to either reductive cleavage of the alpha-nucleofuge or conjugate addition. Good alpha-nucleofuges favored the reduction pathway while poorer nucleofuges favored conjugate addition.

  DOI：

  10.1021/jo00024a014
• 作为产物：
  描述：

  (+/-)-6-acetoxy-4,4-dimethylcyclohex-2-ene-1-one 在 甲醇 、 potassium carbonate 作用下， 生成 6-羟基-4,4-二甲基环己-2-烯-1-酮
  参考文献：
  名称：

  2-Hydroxy-5,5-dimethylcyclohex-2-en-1-one

  摘要：

  The structure of the title compound, C8H12O2, which is a rearrangement product of the reaction of 6-hydroxy-4,4-dimethylcyclohex-2-en-1-one and 4-dimethylaminopyridine has been identified as 2-hydroxy-5,5-dimethylcyclohex-2-en-1-one, The C atom of the six-membered ring connected to the two methyl groups is 0.617(2)Angstrom out of the least-squares plane defined by the other C atoms of the rin. The unit cell consists of discrete molecules with intra-and intermolecular hydrogen bonds.

  DOI：

  10.1107/s0108270197012079

文献信息

• Fragment Coupling Approach to Diaporthein B
  作者：Ian Tingyung Hsu、Seth B. Herzon

  DOI：10.1021/acs.joc.2c02655

  日期：2023.2.17

  pimarane diterpenes. The first approach provided access to the tricyclic carbon scaffold of the target and featured a highly diastereoselective fragment coupling, a novel carbonylative Stille cross-coupling to directly access an α-hydroxyketone from a vinyl iodide, and a tandem aldol cyclization–deprotection cascade. The second route utilized a diastereoselective 1,4-addition of a silyloxyfuran to an unsaturated

  Pimarane 二萜由多种植物、真菌和细菌产生。这个家族的许多成员都具有抗菌和抗增殖活性。pimarane diterpenes 的特点是三环碳骨架包含三个稠合的六元环和至少三个季中心。在这里，我们描述了两种用于合成 diaporthein B ( 3), 一种氧化程度最高的 pimarane 二萜。第一种方法提供了对目标三环碳支架的访问，并具有高度非对映选择性片段偶联、一种新型羰基化 Stille 交叉偶联，可直接从乙烯基碘化物中获得 α-羟基酮，以及串联醛醇环化-脱保护级联。第二条路线利用甲硅烷基氧基呋喃与不饱和酮的非对映选择性 1,4-加成，然后进行环氧化开环序列，以获得包含两个精心设计的环己烷环的高度氧化的中间体。本文开发的化学可能最终可用于此类天然产物的最终合成。
• A general method for the preparation of .gamma.-substituted cyclohexenals and cycloheptenals
  作者：Todd K. Jones、Scott E. Denmark

  DOI：10.1021/jo00221a015

  日期：1985.10
• Functional group hybrids. Reactivity of .alpha.'-nucleofuge .alpha.,.beta.-unsaturated ketones. 2. Reactions with malonate anion. Concerning the mechanism of the Favorskii rearrangement
  作者：Thomas R. Barbee、Hedeel Guy、Mary Jane Heeg、Kim F. Albizati

  DOI：10.1021/jo00024a015

  日期：1991.11

  The scope and limiations of the reaction of alpha'-nucleofuge alpha,beta-unsaturated ketones with sodium dimethyl malonate has been studied systematically. The substrates with good nucleofuges (halides, mesylate) give cyclopropanols upon reaction with malonate anion by way of a conjugate Favorskii reaction. In reactions with substrates containing the poorer nucleofuge (acetoxy) conjugate addition proceeded without entering the Favorskii manifold. Concerning the mechanism of the Favorskii reaction, it is suggested that the loss of the nucleofuge occurs to give a 2-oxyallyl cation, but that disrotatory ring closure is facile and the only products observed result from nucleophilic trapping of cyclopropanones to yield cyclopropanols in fair to good yield.
• Tanyeli; Sezen; Dikici, Enantiomer, 2001, vol. 6, # 4, p. 219 - 277
  作者：Tanyeli、Sezen、Dikici、Fleischhauer、Repges、Wang、Gawronski、Kacprzak

  DOI：——

  日期：——
• Functional group hybrids. Reactivity of .alpha.'-nucleofuge .alpha.,.beta.-unsaturated ketones. 1. Reactions with organocopper reagents
  作者：Thomas R. Barbee、Kim F. Albizati

  DOI：10.1021/jo00024a014

  日期：1991.11

  A series of alpha-nucleofuge alpha',beta'-unsaturated ketones encompassing a variety of structural types and nucleofuges was prepared. Treatment of these compounds with lithium dimethylcuprate or methylcopper leads primarily to either reductive cleavage of the alpha-nucleofuge or conjugate addition. Good alpha-nucleofuges favored the reduction pathway while poorer nucleofuges favored conjugate addition.