3-(4-oxopentyl)-2-cyclohexen-1-one | 57232-69-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-oxopentyl)-2-cyclohexen-1-one
• 英文别名: 3-(4-Oxopentyl)cyclohex-2-en-1-one
• CAS: 57232-69-6
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: PKUGQKJELMBAJQ-UHFFFAOYSA-N

物化性质

• 沸点：
  315.8±31.0 °C(Predicted)
• 密度：
  1.010±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-oxopentyl)-2-cyclohexen-1-one 在 3 A molecular sieve copper(l) iodide 、 sodium hydride 、 二异丁基氢化铝 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 31.58h， 生成 <1RS-(1α,2α,4aα)>-1,2,3,4,4a,5,6,7-octahydro-4a,8-dimethyl-2-(phenylseleno)-1-<<3-(trimethylsilyl)-2-propynyl>oxy>-naphthalene
  参考文献：
  名称：

  Synthesis of (.+-.)-frullanolide: an application of radical closure

  摘要：

  DOI：

  10.1021/jo00290a053
• 作为产物：
  描述：

  5-氯-2-戊酮 在 nickel diacetate 、 lithium diisopropyl amide 作用下， 以 乙醇 为溶剂， 生成 3-(4-oxopentyl)-2-cyclohexen-1-one
  参考文献：
  名称：

  1-Benzyl-2,6-二氰基哌啶类作为新型退火试剂。用于制备稠合多环化合物

  摘要：

  1-苄基-2,6-二烷基-2,6-二氰基哌啶作为退火试剂的效用，即潜在的1,5-二酮，在多稠合化合物的合成中得到证明。

  DOI：

  10.1246/cl.1988.1109

文献信息

• Tandem Conjugate Reduction−Aldol Cyclization Using Stryker's Reagent
  作者：Pauline Chiu、Chun-Pong Szeto、Zhe Geng、Kin-Fai Cheng

  DOI：10.1021/ol015944n

  日期：2001.6.1

  [see reaction]. Conjugate reduction by Stryker's reagent to form copper enolates, followed by intramolecular aldol cyclization, successfully generated five- and six-membered carbocycles in one pot efficiently. This tandem reaction is generally diastereoselective and provides good yields of the beta-hydroxyketones without any dehydration at low temperatures.

  [请参阅反应]。用Stryker试剂还原还原形成烯醇铜，然后分子内羟醛环化，可在一个锅中有效地成功生成五元和六元碳环。该串联反应通常是非对映选择性的，并提供良好的β-羟基酮收率，且在低温下不发生任何脱水。
• Copper-catalyzed 1,4-Addition Reaction of Grignard Reagent to Enones Using Microflow System
  作者：Haruo Katayama、Seijiro Matsubara

  DOI：10.1246/cl.130061

  日期：2013.5.5

  The copper-catalyzed conjugate addition of a Grignard reagent to an α,β-unsaturated ketone was performed in a microflow system. In the reaction using the microflow system, a chemoselective 1,4-addi...

  铜催化的格氏试剂与 α,β-不饱和酮的共轭加成在微流系统中进行。在使用微流系统的反应中，化学选择性 1,4-加...
• Regiospecific Intramolecular Aldol Condensation Induced by Conjugate Addition of lithium dimethylcuprate to ζ-Oxo-α, β-enones preliminary communication [1]
  作者：Ferdinand Näf、René Decorzant、Walter Thommen

  DOI：10.1002/hlca.19750580635

  日期：1975.7.16

  react with lithium dimethylcuprate to give cyclic aldols such as hydroxydecalone 1 and hydroxyspiro[4.5]decanone 2 in a regio- and stereospecific manner. This new reaction, a combination of conjugate methyl addition to α, β-enones with directed intramolecular aldolisation, is suggested to proceed via either enoate anions, such as 8 and 11, or radical anions, such as 9 10 and 12 13, as intermediates

  ζ-Oxo-α，β-烯酮与二甲基铜酸锂反应，以区域和立体有择的方式生成环状羟醛，例如羟基癸酮1和羟基螺[4.5]癸酮2。建议该新反应是将共轭甲基加成至α，β-烯酮并进行定向分子内醛醇缩合的反应，是通过烯酸酯阴离子（例如8和11）或自由基阴离子（例如9 10和12 13）作为中间体进行的。
• Activation of carbonyl function by 1,2-diol; novel asymmetric spirocyclization based on acid-catalysed conjugate addition
  作者：Hiroshi Suemune、Youichi Takahashi、Kiyoshi Sakai

  DOI：10.1039/c39930001858

  日期：——

  Novel asymmetric spirocyclization of 3-(4-oxopentyl)cyclohex-2-en-1-one 3 based on activation of carbonyl function by BF3-(S,S)-cyclohexane-1,2-diol system has been studied to afford the C2-symmetric dione (–)-5 of 85% enantiomeric excess (e.e.) in 86% yield.

  基于 BF3-(S,S)-环己烷-1,2-二醇体系对羰基功能的活化，研究了 3-(4-氧代戊基)环己-2-烯-1-酮 3 的新型不对称螺环化，得到了对映体过量率为 85% (e.e.)的 C2 对称二酮 (-)-5，收率为 86%。
• Asymmetric spirocyclization: A new type of acid-catalyzed intramolecular 1, 4-addition to form carba-spirocyclic compounds
  作者：Satoshi Yamada、Satoru Karasawa、Youichi Takahashi、Mariko Aso、Hiroshi Suemune

  DOI：10.1016/s0040-4020(98)01009-6

  日期：1998.12

  Novel spirocyclization based on intramolecular 1,4-addition and its asymmetric version have been developed using a combination of Lewis acid and 1,2-diol. Treatment of five- and six-membered alpha,beta-unsaturated cyclic ketones having a 4-oxopentyl group at the beta-position with Lewis acid and ethylene glycol gave spiro[4.5]decane-2,7-dione and spiro[5.5]undecane-2,8-dione, respectively. The asymmetric version of this reaction has been developed by using optically active 1,2-diol such as cyclohexane-1,2-diol to afford the spirocyclic products of up to 85% e.e. (C) 1998 Elsevier Science Ltd. All rights reserved.