(Z)-(5-chloropent-1-en-1-yl)benzene | 374094-69-6

• 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: (Z)-(5-chloropent-1-en-1-yl)benzene
• 英文别名: 5-chloro-1-phenyl-1-pentene；(Z)-1-phenyl-5-chloro-1-pentene；[(Z)-5-chloropent-1-enyl]benzene
• CAS: 374094-69-6
• 化学式: C₁₁H₁₃Cl
• 分子量: 180.677
• InChiKey: CDINNLUJIQAPRY-UITAMQMPSA-N

物化性质

• 沸点：
  283.0±19.0 °C(Predicted)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (Z)-(5-chloropent-1-en-1-yl)benzene 在 caesium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 28.0h， 生成 (Z)-N-(4-toluenesulfonyl)-5-phenylpent-4-enylamine
  参考文献：
  名称：

  Oxidative Hydroxylation Mediated by Alkoxysulfonium Ions

  摘要：

  Oxidative hydroxylation of toluene derivatives via alkoxysulfonium ion intermediates was achieved by integration of anodic oxidation and hydrolysis to give benzyl alcohols which are also susceptible to oxidation. Alkenes were also oxidized to give 1,2-diols without overoxidation. The integration of electrochemical oxidative cyclization and hydrolysis was achieved using alkenes bearing a nitrogen atom in an appropriate position to give cyclic beta-amino-substituted alcohols.

  DOI：

  10.1021/ol203467v
• 作为产物：
  描述：

  (5-chloropent-1-ynyl)benzene 在 Lindlar's catalyst 1-己烯 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 以95%的产率得到(Z)-(5-chloropent-1-en-1-yl)benzene
  参考文献：
  名称：

  通过扩环不对称合成（2 S，3 S）-3-羟基-2-苯基哌啶

  摘要：

  的催化对映选择性高（99％ee）的制备ñ -叔-butyloxycarbonyl-（2小号，3小号）-3-羟基-2-苯基-哌啶和ñ -叔-butyloxycarbonyl-（2小号）-2-苯基使用分子内环氧化物开环然后扩环开发了哌啶-3-酮。所述顺式-epoxide起始材料是在经由雅各布森环氧化高ee值可用。

  DOI：

  10.1016/s0040-4039(01)01223-0

文献信息

• Catalytic Enantioselective Arylboration of Alkenylarenes
  作者：Kaitlyn M. Logan、M. Kevin Brown

  DOI：10.1002/anie.201609844

  日期：2017.1.16

  A method for the catalytic enantioselective arylboration of alkenylarenes is disclosed. The reaction leads to the formation of 1,1‐diarylalkanes that also incorporate an additional pinacol boronic ester which can be easily transformed to a variety of groups. The products are formed with excellent diastereoselectivities and enantioselectivities.

  公开了用于烯基芳烃的催化对映选择性芳基硼化的方法。该反应导致形成1,1-二芳基烷烃，该烷烃还掺入了另外的频哪醇硼酸酯，可以轻松转化为各种基团。形成的产物具有优异的非对映选择性和对映选择性。
• Photo-induced Decarboxylative Heck-Type Coupling of Unactivated Aliphatic Acids and Terminal Alkenes in the Absence of Sacrificial Hydrogen Acceptors
  作者：Hui Cao、Heming Jiang、Hongyu Feng、Jeric Mun Chung Kwan、Xiaogang Liu、Jie Wu

  DOI：10.1021/jacs.8b11218

  日期：2018.11.28

  boronates are among the most versatile building blocks that can be found in every sector of chemical science. We herein report a noble-metal-free method of accessing such olefins through a photo-induced decarboxylative Heck-type coupling using alkyl carboxylic acids, one of the most ubiquitous building blocks, as the feedstocks. This transformation was achieved in the absence of external oxidants through

  1,2-二取代的烯烃，如乙烯基芳烃、乙烯基硅烷和乙烯基硼酸酯，是化学科学各个领域中最通用的结构单元。我们在此报告了一种无贵金属的方法，该方法使用烷基羧酸（最普遍的结构单元之一）作为原料，通过光诱导脱羧 Heck 型偶联获得此类烯烃。这种转变是在没有外部氧化剂的情况下通过有机光氧化还原催化剂和钴肟催化剂的协同组合实现的，H2 和 CO2 作为唯一的副产物。控制实验和 DFT 计算都支持基于自由基的机制，最终导致开发出脂肪族羧酸、丙烯酸酯和乙烯基芳烃的选择性三组分偶联。
• Asymmetric synthesis of (2S,3S)-3-hydroxy-2-phenylpiperidine via ring expansion
  作者：Jaemoon Lee、Thoa Hoang、Stephanie Lewis、Steven A Weissman、David Askin、R.P Volante、P.J Reider

  DOI：10.1016/s0040-4039(01)01223-0

  日期：2001.9

  A catalytic highly enantioselective (99% ee) preparation of N-tert-butyloxycarbonyl-(2S,3S)-3-hydroxy-2-phenyl-piperidine and N-tert-butyloxycarbonyl-(2S)-2-phenyl-piperidin-3-one was developed using an intramolecular epoxide opening followed by ring expansion. The cis-epoxide starting material was available in high ee via Jacobsen epoxidation.

  的催化对映选择性高（99％ee）的制备ñ -叔-butyloxycarbonyl-（2小号，3小号）-3-羟基-2-苯基-哌啶和ñ -叔-butyloxycarbonyl-（2小号）-2-苯基使用分子内环氧化物开环然后扩环开发了哌啶-3-酮。所述顺式-epoxide起始材料是在经由雅各布森环氧化高ee值可用。
• Catalytic Chemoselective and Stereoselective Semihydrogenation of Alkynes to <i>E</i>-Alkenes Using the Combination of Pd Catalyst and ZnI₂
  作者：Radhouan Maazaoui、Raoudha Abderrahim、Fabrice Chemla、Franck Ferreira、Alejandro Perez-Luna、Olivier Jackowski

  DOI：10.1021/acs.orglett.8b03295

  日期：2018.12.7

  An efficient E-selective semihydrogenation of internal alkynes was developed under low dihydrogen pressure and low reaction temperature from commercially available reagents: Cl2Pd(PPh3)(2), Zn-0, and ZnI2. Kinetic studies and control experiments underline the significant role of ZnI2 in this process under H-2 atmosphere, establishing that the transformation involves syn-hydrogenation followed by isomerization. This simple and easy-to-handle system provides a route to E-alkenes under mild conditions.
• Oxidative Hydroxylation Mediated by Alkoxysulfonium Ions
  作者：Yosuke Ashikari、Toshiki Nokami、Jun-ichi Yoshida

  DOI：10.1021/ol203467v

  日期：2012.2.3

  Oxidative hydroxylation of toluene derivatives via alkoxysulfonium ion intermediates was achieved by integration of anodic oxidation and hydrolysis to give benzyl alcohols which are also susceptible to oxidation. Alkenes were also oxidized to give 1,2-diols without overoxidation. The integration of electrochemical oxidative cyclization and hydrolysis was achieved using alkenes bearing a nitrogen atom in an appropriate position to give cyclic beta-amino-substituted alcohols.