3-(4-methylphenyl)but-2-enoyl chloride | 60796-10-3

• 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: 3-(4-methylphenyl)but-2-enoyl chloride
• CAS: 60796-10-3
• 化学式: C₁₁H₁₁ClO
• 分子量: 194.661
• InChiKey: DZKJAXITMVEBMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  4'-氯-2,2,2-三氟苯乙酮 、 3-(4-methylphenyl)but-2-enoyl chloride 在 BF₄*C₃₀H₃₆N₃OSi⁽¹⁺⁾ 、 caesium carbonate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 (RS)-4-(4-methylphenyl)-6-(trifluoromethyl)-6-(4-chlorophenyl)-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  N-杂环碳烯催化的不饱和酰基氯和酮的环化

  摘要：

  光学活性的三氟甲基二氢吡喃酮和螺环的羟吲哚-二氢吡喃酮的直接合成已经通过手性N-杂环卡宾催化的α，β-不饱和β-甲基酰氯与活化的三氟甲基酮或靛红衍生物的环化反应而实现。

  DOI：

  10.1002/adsc.201100178

文献信息

• Catalytic [4+2] Cyclization of α,β-Unsaturated Acyl Chlorides with 3-Alkylenyloxindoles: Highly Diastereo- and Enantioselective Synthesis of Spirocarbocyclic Oxindoles
  作者：Li-Tao Shen、Wen-Qiang Jia、Song Ye

  DOI：10.1002/anie.201207405

  日期：2013.1.7

  Cinchona alkaloids were used as Lewis base catalysts in the title reaction. The [4+2] cyclization of α,β‐unsaturated acyl chlorides with electron‐deficient alkenes derived from oxindole gave the corresponding spirocarbocyclic oxindoles.

  金鸡纳生物碱在标题反应中用作路易斯碱催化剂。α，β-不饱和酰氯与衍生自氧吲哚的缺电子烯烃的环化[4 + 2]得到了相应的螺碳环羰基吲哚。
• Organocatalytic [4 + 2] cyclocondensation of α,β-unsaturated acyl chlorides with imines: highly enantioselective synthesis of dihydropyridinone and piperidine derivatives
  作者：Wen-Qiang Jia、Xiang-Yu Chen、Li-Hui Sun、Song Ye

  DOI：10.1039/c4ob00114a

  日期：——

  alkaloid-catalyzed [4 + 2] cyclocondensation of α,β-unsaturated acyl chlorides with imines is developed to give the corresponding substituted dihydropyridinones in good yields with high to excellent enantioselectivities. Reduction of the dihydropyridinones gave highly optically active substituted tetrahydropyridinone and piperidine derivatives.

  开发了金鸡纳生物碱催化的亚胺与α，β-不饱和酰氯的[4 + 2]环缩合反应，可以以高收率和高至优异的对映选择性提供相应的取代二氢吡啶并酮。二氢吡啶酮的还原得到高度旋光的取代的四氢吡啶酮和哌啶衍生物。
• <i>N</i>-Heterocyclic Carbene-Catalyzed All Carbon-[4+2] Cyclocondensation of<i>α</i>,<i>β</i>-Unsaturated Acyl Chlorides with 3-Alkylenyloxindoles
  作者：Litao Shen、Wenqiang Jia、Song Ye

  DOI：10.1002/cjoc.201400411

  日期：2014.8

  AbstractAlthough the NHC‐catalyzed cyclization reactions have been well established for the synthesis of various heterocycles, the corresponding all carbon cyclization reaction for the synthesis of carbocycles is far less established. In this note, the NHC‐catalyzed all carbon [4+2] cyclocondensation of α,β‐unsaturated acyl chlorides and 3‐alkenyloxindoles was developed to give the corresponding spirocarbocyclic oxindoles in good yield with good to high diastereoselectivities.