1-(2-乙烯基环己基)乙酮 | 117369-95-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2-乙烯基环己基)乙酮
• 英文名称: 1-(2-vinylcyclohexyl)ethanone
• 英文别名: 1-Acetyl-2-ethenylcyclohexane；1-acetyl-2-vinylcyclohexane；Ethanone, 1-(2-ethenylcyclohexyl)-(9CI)；1-(2-ethenylcyclohexyl)ethanone
• CAS: 117369-95-6
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: HPBAEOFKEKXJNX-UHFFFAOYSA-N

物化性质

• 沸点：
  210.8±29.0 °C(Predicted)
• 密度：
  0.960±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2-乙烯基环己基)乙酮 在 正丁基锂 、 sodium methylate 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 66.8h， 生成 trans-3-phenyl-1-(2-vinylcyclohexyl)propan-1-one
  参考文献：
  名称：

  Investigation on Amino-Heck Cyclization of 1-(2-Vinylcyclohexyl)ketone Diethyl Phosphinyloximes

  摘要：

  Upon the treatment with Pd(PPh3)4 and Et3N in DMF at 80 degrees C, a range of trans-1-(2-vinylcyclohexyl)-substituted ketone diethylphosphinyloximes underwent the cyclization in a 6-endo pathway to afford 1-substituted tetrahydroisoquinolines in varying yields. Among which, the reactions of the substrates bearing the saturated alkyl groups were severely competed by hydrolysis and/or Beckmann rearrangement, while these undesired side reactions could be suppressed by introducing a beta-aryl moiety possibly due to the stabilizing pi-pi stacking interactions between the phosphoryl and/or vinyl group and the aryl rings.

  DOI：

  10.3987/com-11-12396
• 作为产物：
  描述：

  1-[2-(1-hydroxyethyl)cyclohexyl]ethanone 生成 1-(2-乙烯基环己基)乙酮
  参考文献：
  名称：

  ARAKI, MASASI;XIBI, TAKUO

  摘要：

  DOI：

文献信息

• Multisubstituted Cyclohexene Construction through Telescoped Radical-Addition Induced Remote Functional Group Migration and Horner–Wadsworth–Emmons (HWE) Olefination
  作者：Xing-Gui Zhang、Xin Li、Chi Zhang、Chao Feng

  DOI：10.1021/acs.orglett.1c03821

  日期：2021.12.17

  photoredox-promoted alkene difunctionalization via remote functional group migration with concomitant intramolecular Horner–Wadsworth–Emmons (HWE) olefination. The characteristic feature of this protocol resides in the fact that the follow-up requiring ketone functionality for ring-closing olefination is in situ unveiled from the otherwise inert tertiary alcohol by the preceding alkene difunctionalization

  本文介绍了一种用于快速组装多取代环己烯的有效伸缩方法。整个过程通过远程官能团迁移很好地将光氧化还原促进的烯烃双官能化与伴随的分子内 Horner-Wadsworth-Emmons (HWE) 烯化结合起来。该协议的特征在于，后续需要酮官能团进行闭环烯烃化的事实是通过前面的烯烃双官能化从原本惰性的叔醇中原位揭开的。
• Rhodium-Catalyzed Intramolecular Cyclopropanation of α-Diazo β-Keto Nitriles Containing an Unsaturated Substituted Cycloalkyl Group
  作者：Jia-Liang Zhu、Yung-Peng Wu

  DOI：10.1055/s-0036-1588174

  日期：2017.7

  α-diazo β-keto nitriles bearing trans-2-allyl-, -vinyl-, or -phenylcycloalkyl groups were prepared and their intramolecular cyclopropanation reactions were examined. In the presence of Rh2(OAc)4 (1 mol%) as a catalyst, the allyl- and vinyl-substituted precursors were found to undergo cyclopropanation smoothly at ambient temperature to afford novel tricyclic α-keto cyclopropyl nitriles in 47–88% yields

  制备了几种带有反式-2-烯丙基-、-乙烯基-或-苯基环烷基的α-重氮β-酮腈，并研究了它们的分子内环丙烷化反应。在 Rh2(OAc)4 (1 mol%) 作为催化剂存在下，发现烯丙基和乙烯基取代的前体在环境温度下顺利进行环丙烷化，以 47-88% 的产率提供新型三环 α-酮基环丙基腈非对映体比例范围为 79:21 至 >99:1。另一方面，含苯基类似物的催化反应没有产生任何环丙基产物，而是以定量产率提供官能化的六氢菲或四氢环戊萘衍生物。
• Stereoselective construction of quaternary centers at ambient temperature by the highly stereocontrolled migration of groups containing sp-, sp2-, and sp3-hybridized carbon atoms
  作者：Charles M. Marson、Andrew J. Walker、Jane Pickering、Adrian D. Hobson、Roger Wrigglesworth、Simon J. Edge

  DOI：10.1021/jo00074a019

  日期：1993.10

  A very highly diastereoselective semipinacol rearrangement of 2,3-epoxy alcohols mediated by tin(IV) chloride at ambient temperatures is shown to be applicable to a wide variety of migrating groups including methyl, tert-butyl, cyclopropyl, vinyl, alkynyl, phenyl, and 2-furyl. A synthetically valuable feature is that a mixture of syn- and anti-epoxy alcohols affords only a single diastereoisomerically pure beta-hydroxy ketone. Additional advantages of the reaction include the presence in the product of two adjacent stereocenters and the efficient creation of a new quaternary center, valuable features in the synthesis of a variety of natural products.
• Manganese(III)-based oxidative free-radical cyclizations. Oxidative cyclization and aromatization of 3-oxo-6-heptenoate esters
  作者：Barry B . Snider、Jeffrey J. Patricia

  DOI：10.1021/jo00262a016

  日期：1989.1
• Synthesis of .omega.-bromo ketones
  作者：Herbert O. House、Chia-Yeh Chu、William V. Phillips、Trevor S. B. Sayer、Cheuk-Chung Yau

  DOI：10.1021/jo00430a009

  日期：1977.5