4-chloro-4-phenylbut-3-en-2-one | 91667-26-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-chloro-4-phenylbut-3-en-2-one
• 英文别名: 1-Phenyl-3-oxo-trans-buten-(1)-ylchlorid；(E)-4-chloro-4-phenylbut-3-en-2-one
• CAS: 91667-26-4
• 化学式: C₁₀H₉ClO
• 分子量: 180.634
• InChiKey: ACMZBZXKCMCEQW-JXMROGBWSA-N

物化性质

• 沸点：
  137-138 °C(Press: 10 Torr)
• 密度：
  1.2373 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  苯乙炔 在 四氟硼酸-二乙醚络合物 、 三甲基氯硅烷 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 2-甲基四氢呋喃 为溶剂， 反应 24.33h， 生成 (Z)-4-chloro-4-phenylbut-3-en-2-one 、 4-chloro-4-phenylbut-3-en-2-one
  参考文献：
  名称：

  Synthesis of (Z)-β-halo α,β-unsaturated carbonyl systems via the combination of halotrimethylsilane and tetrafluoroboric acid

  摘要：

  通过对炔酮进行HX的共轭加成，已开发出一种β-卤乙烯衍生物的立体选择性合成方法。

  DOI：

  10.1039/c8ob02110d

文献信息

• Metal-free, Regio-, and Stereo-Controlled Hydrochlorination and Hydrobromination of Ynones and Ynamides
  作者：Xiaojun Zeng、Zhichao Lu、Shiwen Liu、Gerald B. Hammond、Bo Xu

  DOI：10.1021/acs.joc.7b02257

  日期：2017.12.15

  We developed an atom-economical and metal-free method for the regio- and stereo-selective hydrohalogenation of ynones and ynamides using easy to handle DMPU/HX (X = Br or Cl) reagents. The reaction operates under mild conditions and a range of functional groups is well tolerated. We propose that the hydrohalogenation of ynones gives the anti-addition products via a concerted multimolecular AdE3 mechanism

  我们开发了一种原子经济且无金属的方法，可使用易于处理的DMPU / HX（X = Br或Cl）试剂对炔酮和乙酰胺进行区域和立体选择性氢卤化反应。该反应在温和的条件下进行，并且对一系列官能团的耐受性良好。我们建议ynones的氢卤化使反通过协调一致的多分子广告-addition产品ë 3机制和ynamides的氢卤化产生SYN通过阳离子keteniminium中间-addition产品。
• Regioselective synthesis of (trifluoromethyl)-β-chloroenones
  作者：Gérard Alvernhe、Abdelkader Bensadat、Abdelkader Ghobsi、André Laurent、Eliane Laurent

  DOI：10.1016/s0022-1139(96)03523-3

  日期：1997.3

  The regioselectivity of the conversion of 1,3-diketones into beta-chloroenones can be changed by the appropriate choice of the reagent: reaction with ''Vilsmeier's reagent'' prepared from POCl3 and dimethylformamide or treatment of the diketone with the oxalyl chloride in the presence of dimethylformamide.
• MANOIU D.; MANOIU M.; DINULESCU I. G.; AVRAM M., REV. ROUM. CHIM., 29,(1986) N 2, 201-206
  作者：MANOIU D.、 MANOIU M.、 DINULESCU I. G.、 AVRAM M.

  DOI：——

  日期：——
• MANOIU D.; MANOIU M.; DINULESCU I. G.; AVRAM M., REV. ROUM. CHIM., 29,(1984) N 2, 193-199
  作者：MANOIU D.、 MANOIU M.、 DINULESCU I. G.、 AVRAM M.

  DOI：——

  日期：——
• [EN] CATALYTIC ASYMMETRIC SYNTHESIS OF OPTICALLY ACTIVE COMPOUNDS<br/>[FR] SYNTHESE ASYMETRIQUE CATALYTIQUE DE COMPOSES OPTIQUEMENT ACTIFS
  申请人：CHEMINOVA AS

  公开号：WO2003050105A2

  公开（公告）日：2003-06-19

  A one step catalytic asymmetric process for the synthesis of an optically active compound of formula la or lb wherein R is selected from C1-7 alkyl, C1-7 haloalkyl, C1-7 alkoxy, C1-7 haloalkoxy, halogen and hydroxy; R3 is H or C1-4 alkyl; R4 is selected from H, C1-7 alkyl, C1-7 haloalkyl, C1-7 alkoxy, COOH, CO-C1-7 alkoxy and an optionally substituted aryl or heterocycle; AR represents C1-7 alkyl, optionally substituted aryl, an optionally substituted heterocycle or AR and R4 may be bridged together forming part of a ring system; X is O or S; m is a number between 0-4; comprising the step of reacting a compound of the formula 2 with a compound of formula 3 in the presence of a catalytic amount of a chiral nitrogen containing organic compound.