1-<4-<(Z)-Hex-1-enyl>phenyl>ethanon | 137365-00-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-<4-<(Z)-Hex-1-enyl>phenyl>ethanon
• 英文别名: (Z)-1-[4-(hex-1-enyl)phenyl]ethanone；(Z)-1-(1-acylphenyl)-1-hexene；(Z)-1-(4-(hex-1-en-1-yl)phenyl)ethanone；1-[4-[(Z)-hex-1-enyl]phenyl]ethanone
• CAS: 137365-00-5
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: BWEPZNANRIFTAF-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• 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：

  4-(1-hexyn-1-yl)acetophenone 在 [(6-Mes)Cu(OtBu)] 作用下， 以 氘代苯 、 叔丁醇 为溶剂， 反应 3.0h， 以35%的产率得到1-<4-<(Z)-Hex-1-enyl>phenyl>ethanon
  参考文献：
  名称：

  铜-NHC介导的炔烃的半氢化和氢硼化：使用环扩碳烯的增强的催化活性。

  摘要：

  由（NHC）CuMes与t BuOH质子分解制得的一系列带有五元，六元和七元环N-杂环卡宾的二配位叔丁醇铜配合物已被用作苯甲酸半加氢反应的催化前体。炔烃与硅烷/ t BuOH的混合，以及炔烃与HBPin的硼氢化。两种方法都具有较高的区域选择性，并显示六元和七元环卡宾具有增强作用。

  DOI：

  10.1021/acs.organomet.8b00467

文献信息

• A Versatile Catalyst for Heck Reactions of Aryl Chlorides and Aryl Bromides under Mild Conditions
  作者：Adam F. Littke、Gregory C. Fu

  DOI：10.1021/ja010988c

  日期：2001.7.1

  for Heck reactions of aryl chlorides and bromides. A sterically and electronically diverse array of aryl bromides, as well as activated aryl chlorides, couple with a range of mono- and disubstituted olefins at room temperature, furnishing the arylated product with high E/Z stereoselection. The corresponding reactions of a broad spectrum of electron-neutral and electron-rich aryl chlorides proceed at

  在 Cy2NMe 存在下，Pd/P(t-Bu)3 可作为一种非常温和且用途广泛的催化剂，用于芳基氯化物和溴化物的 Heck 反应。空间和电子上不同的芳基溴化物阵列以及活化的芳基氯化物，在室温下与一系列单取代和双取代的烯烃偶联，为芳基化产物提供高 E/Z 立体选择。广泛的电子中性和富电子芳基氯化物的相应反应在升高的温度下进行，并且具有高选择性。在范围和温和性方面，Pd/P(t-Bu)3/Cy2NMe 代表了先前报道的这些 Heck 偶联过程的催化剂的进步。
• Kauffmann, Thomas; Laarmann, Barbara; Menges, Detlef, Chemische Berichte, 1992, vol. 125, # 1, p. 163 - 169
  作者：Kauffmann, Thomas、Laarmann, Barbara、Menges, Detlef、Neiteler, Gabriele

  DOI：——

  日期：——
• Nanoporous Gold Catalyst for Highly Selective Semihydrogenation of Alkynes: Remarkable Effect of Amine Additives
  作者：Mei Yan、Tienan Jin、Yoshifumi Ishikawa、Taketoshi Minato、Takeshi Fujita、Lu-Yang Chen、Ming Bao、Naoki Asao、Ming-Wei Chen、Yoshinori Yamamoto

  DOI：10.1021/ja3087592

  日期：2012.10.24

  We report for the first time the highly selective semihydrogenation of alkynes using the unsupported nanoporous gold (AuNPore) as a catalyst and organosilanes with water as a hydrogen source. Under the optimized reaction conditions, the present semihydrogenation of various terminal- and internal-alkynes affords the corresponding alkenes in high chemical yields and excellent Z-selectivity without any, over-reduced alkanes. The use of DMF as solvent, which generates amines in situ, or pyridine as an additive is crucial to suppress the association of hydrogen atoms on AuNPore to form H-2 gas, which is unable to reduce alkynes on the unsupported gold catalysts. The AuNPore catalyst can be readily recovered and reused without any loss of catalytic activity. In addition, the SEM and TEM characterization of nanoporosity show that the AuNPore catalyst has a bicontinuous 3D structure and a high density of atomic steps and kinks on ligament surfaces, which should be one of the important origins of catalytic activity.
• HECK REACTIONS OF ARYL CHLORIDES CATALYZED BY PALLADIUM/TRI-tert-BUTYLPHOSPHINE: (E)-2-METHYL-3-PHENYLACRYLIC ACID BUTYL ESTER AND (E)-4-(2-PHENYLETHENYL)BENZONITRILE
  作者：Littke, Adam F.、Fu, Gregory C.、Ober, Michael H.、Denmark, Scott E.

  DOI：10.15227/orgsyn.081.0063

  日期：——
• Copper-NHC-Mediated Semihydrogenation and Hydroboration of Alkynes: Enhanced Catalytic Activity Using Ring-Expanded Carbenes
  作者：Jonathan W. Hall、Darcy M. L. Unson、Paul Brunel、Lee R. Collins、Mateusz K. Cybulski、Mary F. Mahon、Michael K. Whittlesey

  DOI：10.1021/acs.organomet.8b00467

  日期：2018.9.24

  tert-butoxide complexes bearing five-, six-, and seven-membered ring N-heterocyclic carbenes, prepared by protonolysis of (NHC)CuMes with tBuOH, have been used as catalytic precursors in the semihydrogenation of alkynes with silanes/tBuOH and the hydroboration of alkynes with HBPin. Both processes proceed with high regioselectivity and show enhancements with six- and seven-membered ring carbenes.

  由（NHC）CuMes与t BuOH质子分解制得的一系列带有五元，六元和七元环N-杂环卡宾的二配位叔丁醇铜配合物已被用作苯甲酸半加氢反应的催化前体。炔烃与硅烷/ t BuOH的混合，以及炔烃与HBPin的硼氢化。两种方法都具有较高的区域选择性，并显示六元和七元环卡宾具有增强作用。