3-<(Z)-2-phenyl-1-ethenyl>cyclohexanone | 131025-95-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-<(Z)-2-phenyl-1-ethenyl>cyclohexanone
• 英文别名: (Z)-3-(2-phenylethyl)cyclohexanone；3-[(Z)-2-phenylethenyl]cyclohexan-1-one
• CAS: 131025-95-1
• 化学式: C₁₄H₁₆O
• 分子量: 200.28
• InChiKey: RZPGPHOPONHPGL-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 、 β-溴苯乙烯 在 叔丁基锂 、 indium(III) chloride 作用下， 以 乙醚 、 正戊烷 、 四氢呋喃 、 various solvents 为溶剂， 反应 2.0h， 以35%的产率得到3-<(Z)-2-phenyl-1-ethenyl>cyclohexanone
  参考文献：
  名称：

  Radical reactions initiated by the photochemical cleavage of carbon–indium bonds of organoindium compounds

  摘要：

  Intra- and intermolecular reactions of carbon-centered radicals generated by photolysis of organoindium compounds were examined. The photolysis of vinylindium compounds and indium acetylides provided vinyl and alkynyl radicals, respectively, which were trapped with ethyl iodoacetate giving the corresponding beta,gamma-unsaturated esters. Allylic indium compounds, prepared from 8-bromo- or 8-iodooct-1,6-dienes and powdered indium metal, underwent an intramolecular radical cyclization to afford the 5-exo-trig product. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.013

文献信息

• Organo[2-(hydroxymethyl)phenyl]dimethylsilanes as Mild and Reproducible Agents for Rhodium-Catalyzed 1,4-Addition Reactions
  作者：Yoshiaki Nakao、Jinshui Chen、Hidekazu Imanaka、Tamejiro Hiyama、Yoshitaka Ichikawa、Wei-Liang Duan、Ryo Shintani、Tamio Hayashi

  DOI：10.1021/ja071969r

  日期：2007.7.1

  achievement of the corresponding enantioselective transformations using the tetraorganosilicon reagents, providing the silicon-based approach to optically active ketones and substituted piperidones that serve as synthetic intermediates of pharmaceuticals. A rhodium alkoxide species is suggested to be responsible for a transmetalation step on the basis of the observed kinetic resolution of a racemic chiral phenylsilane

  稳定且可重复使用的四有机硅试剂、烯基-、芳基-和甲硅烷基[2-(羟甲基)苯基]二甲基硅烷，在温和的铑催化下与 α,β-不饱和羰基受体发生 1,4-加成反应。该反应耐受多种官能团，适用于克级合成。手性二烯配体的使用允许使用四有机硅试剂实现相应的对映选择性转化，为用作药物合成中间体的光学活性酮和取代哌啶酮提供基于硅的方法。根据观察到的对映选择性 1 中的外消旋手性苯基硅烷的动力学分辨率，建议铑醇盐物种负责金属转移步骤，
• A new approach to organomanganese compounds: the tellurium/manganese exchange reaction
  作者：Márcio S. Silva、João V. Comasseto、Alcindo A. Dos Santos

  DOI：10.1016/j.tetlet.2010.08.005

  日期：2010.10

  Diorganomanganese compounds react with aryl, vinyl, and alkynyl tellurides in a tellurium/manganese exchange reaction. The new mixed organomanganese reagents react selectively with electrophiles.

  二有机锰化合物在碲/锰交换反应中与芳基，乙烯基和炔基碲化物反应。新的混合有机锰试剂与亲电子试剂选择性反应。
• Tellurium in Organic Synthesis. Preparation of <i>Z</i>-Vinylic Cuprates from <i>Z</i>-Vinylic Tellurides and Their Reaction with Enones and Epoxides
  作者：Fábio C. Tucci、André Chieffi、João V. Comasseto、Joseph P. Marino

  DOI：10.1021/jo951547c

  日期：1996.1.1

  Z-Vinylic tellurides, obtained with 100% stereoselectivity by the hydrotelluration of acetylenes, are easily transformed into Z-vinylic higher order cyanocuprates by reaction with preformed Me(2)Cu(CN)Li-2, n-Bu(2)Cu(CN)Li-2, or n-Bu(2-Th)Cu(CN)Li-2, with total retention of the double-bond configuration. The resulting vinylic higher order cyanocuprates react with unhindered enones to give the corresponding 1,4-addition products in good yields. Reaction of the vinylic higher order cyanocuprates with monosubstituted epoxides at 0 degrees C gives the homoallylic alcohols resulting from the attack to the less-substituted carbon atom, while the disubstituted epoxides failed to react. Allylic epoxides react at -78 degrees C with the vinylic higher order cyanocuprates to give mixtures of 1,2- and 1,4-opening products, the 1,4-product predominating. In all cases the double-bond configuration of the original vinylic telluride was preserved. The vinylic cuprates derived from simple vinylic tellurides and conjugated 1-telluroenynes react with epoxides at 0 degrees C, while vinylic cuprates derived from conjugated 1-tellurodienes required the addition of 1 equiv of BF3 . Et(2)O to give the homoallylic alcohols on reaction with epoxides. The opening of optically pure epoxides through tellurium/copper transmetalation is stereospecific, giving one single stereoisomer of the corresponding homoallylic alcohol.
• Preparation and reactivity of cyanocuprates containing alkylseleno and alkyltelluro groups as non-transferable ligands
  作者：Fabiano K Zinn、Eduardo C Ramos、João V Comasseto

  DOI：10.1016/s0040-4039(01)00187-3

  日期：2001.3

  Alkylseleno and alkyltelluro groups are efficient non-transferable ligands of cyanocuprates in 1,4-addition reactions to enones. (C) 2001 Published by Elsevier Science Ltd.
• Higher order vinyl cyanocuprates from vinylic tellurides
  作者：Fábio C. Tucci、André Chieffi、João V. Comasseto

  DOI：10.1016/0040-4039(92)89015-5

  日期：1992.9

  Bis-vinylic tellurides, 1-tellurodienes, 1-telluroenynes and vinyl thienyl tellurides react with higher order cyanocuprates giving the corresponding higher order vinyl cyanocuprates with retention of the olefine geometry.