(E)-1-(4-bromophenyl)-4,4-dimethylpent-2-en-1-one

• 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: (E)-1-(4-bromophenyl)-4,4-dimethylpent-2-en-1-one
• 化学式: C₁₃H₁₅BrO
• 分子量: 267.166
• InChiKey: PXQBJTVPEHPCRY-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  硫代苯甲酸 、 (E)-1-(4-bromophenyl)-4,4-dimethylpent-2-en-1-one 在 N-[3,5-双（三氟甲基）苯基]-N''-[（8α，9S）-6''-甲氧基七氢呋喃-9-基]脲 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 、
  参考文献：
  名称：

  Enantioselective sulfa-Michael addition of thioacids to α,β-unsaturated ketones with bifunctional organocatalyst

  摘要：

  Organocatalytic conjugate addition of thioacids to alpha,beta-unsaturated ketones has been studied in the presence of cinchona alkaloid derived urea catalyst. Both the enantiomers of products are accessible with the same level of enantioselectivity using pseudoenantiomeric quinine/quinidine derived catalysts. The catalytic process provides optically active thioesters with high chemical yields (up to 99%) and useful enantiselectivity (up to 83% ee). The reaction was performed with 1 mol % of catalyst in toluene at room temperature. A transition state model has been proposed to explain the stereochemical outcome of the reaction. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2012.02.052
• 作为产物：
  描述：

  3,3-二甲基-1-丁炔 、 4-溴苯甲酰氯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 四丁基氟化铵 polymethylhydrosiloxane 、 三(2-呋喃基)膦 、 三甲基氟锡烷 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以99%的产率得到(E)-1-(4-bromophenyl)-4,4-dimethylpent-2-en-1-one
  参考文献：
  名称：

  一锅钯催化加氢锡化/苯乙烯反应，以酰氯为亲电子试剂

  摘要：

  已经开发了适用于使用酰氯亲电试剂的一锅加氢锡烷/ Stille偶联序列。在该方案中，使用Me 3 SnF / PMHS作为原位三甲基氢化锡源进行钯介导的炔烃氢化，然后在单个罐中添加酰氯，以提供多种α，β-不饱和酮。

  DOI：

  10.1016/j.jorganchem.2005.11.041

文献信息

• One-pot Pd-catalyzed hydrostannation/Stille reaction with acid chlorides as the electrophiles
  作者：Kyoungsoo Lee、William P. Gallagher、Elli A. Toskey、Wenzheng Chong、Robert E. Maleczka

  DOI：10.1016/j.jorganchem.2005.11.041

  日期：2006.4

  sequence amenable to the employment of acid chloride electrophiles has been developed. In this protocol, palladium mediated alkyne hydrostannations using Me3SnF/PMHS as an in situ trimethyltin hydride source are followed by the addition of the acid chloride to afford a variety of α,β-unsaturated ketones in a single pot.

  已经开发了适用于使用酰氯亲电试剂的一锅加氢锡烷/ Stille偶联序列。在该方案中，使用Me 3 SnF / PMHS作为原位三甲基氢化锡源进行钯介导的炔烃氢化，然后在单个罐中添加酰氯，以提供多种α，β-不饱和酮。
• Enantioselective sulfa-Michael addition of thioacids to α,β-unsaturated ketones with bifunctional organocatalyst
  作者：Nirmal K. Rana、Rajshekhar Unhale、Vinod K. Singh

  DOI：10.1016/j.tetlet.2012.02.052

  日期：2012.4

  Organocatalytic conjugate addition of thioacids to alpha,beta-unsaturated ketones has been studied in the presence of cinchona alkaloid derived urea catalyst. Both the enantiomers of products are accessible with the same level of enantioselectivity using pseudoenantiomeric quinine/quinidine derived catalysts. The catalytic process provides optically active thioesters with high chemical yields (up to 99%) and useful enantiselectivity (up to 83% ee). The reaction was performed with 1 mol % of catalyst in toluene at room temperature. A transition state model has been proposed to explain the stereochemical outcome of the reaction. (C) 2012 Published by Elsevier Ltd.