(Z)-3-((2-bromophenyl)(hydroxy)methyl)-4-phenylbut-3-en-2-one | 960600-91-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (Z)-3-((2-bromophenyl)(hydroxy)methyl)-4-phenylbut-3-en-2-one
• 英文别名: (R,Z)-3-((2-bromophenyl)(hydroxy)methyl)-4-phenylbut-3-en-2-one；(Z)-3-[(R)-(2-bromophenyl)-hydroxymethyl]-4-phenylbut-3-en-2-one
• CAS: 960600-91-3
• 化学式: C₁₇H₁₅BrO₂
• 分子量: 331.209
• InChiKey: FQAUXWAMEJSSGR-JMPLCFMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-3-((2-bromophenyl)(hydroxy)methyl)-4-phenylbut-3-en-2-one 在 1,2,2,6,6-五甲基哌啶 、 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.42h， 以85%的产率得到1-[(1S)-3-hydroxy-1-phenyl-1H-inden-2-yl]ethanone
  参考文献：
  名称：

  Enantioselective Synthesis of Substituted Indanones from Silyloxyallenes

  摘要：

  A new approach for the synthesis of enantioenriched indanones by asymmetric carbonyl-ene/intramolecular Heck cyclization from racemic silyloxyallenes has been developed. The modular procedure affords highly substituted indenes and indanones with excellent chirality transfer from the optically active carbinols. Full transfer of stereochemical information is achieved in the presence of 1,2,2,6,6-pentamethylpiperidine and PdCl2(PPh3)(2) (1 mol %) in DMF under microwave heating. Short reaction times and high yields have been demonstrated on a variety of substrates.

  DOI：

  10.1021/ja909669e
• 作为产物：
  描述：

  、 邻溴苯甲醛 在 (R,R)-N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminochromium(III) hexafluoroantimonate 、 2,6-二叔丁基-4-甲基吡啶 、 盐酸 作用下， 以 二氯甲烷 、 四氢呋喃 、 水 为溶剂， 反应 0.25h， 生成 (Z)-3-((2-bromophenyl)(hydroxy)methyl)-4-phenylbut-3-en-2-one
  参考文献：
  名称：

  Enantioselective Synthesis of Substituted Indanones from Silyloxyallenes

  摘要：

  A new approach for the synthesis of enantioenriched indanones by asymmetric carbonyl-ene/intramolecular Heck cyclization from racemic silyloxyallenes has been developed. The modular procedure affords highly substituted indenes and indanones with excellent chirality transfer from the optically active carbinols. Full transfer of stereochemical information is achieved in the presence of 1,2,2,6,6-pentamethylpiperidine and PdCl2(PPh3)(2) (1 mol %) in DMF under microwave heating. Short reaction times and high yields have been demonstrated on a variety of substrates.

  DOI：

  10.1021/ja909669e

文献信息

• Catalytic Enantioselective α-Acylvinyl Anion Reactions of Silyloxyallenes
  作者：Troy E. Reynolds、Karl A. Scheidt

  DOI：10.1002/anie.200702818

  日期：2007.10.15
• Enantioselective Synthesis of Substituted Indanones from Silyloxyallenes
  作者：Jonathan A. Brekan、Troy E. Reynolds、Karl A. Scheidt

  DOI：10.1021/ja909669e

  日期：2010.2.10

  A new approach for the synthesis of enantioenriched indanones by asymmetric carbonyl-ene/intramolecular Heck cyclization from racemic silyloxyallenes has been developed. The modular procedure affords highly substituted indenes and indanones with excellent chirality transfer from the optically active carbinols. Full transfer of stereochemical information is achieved in the presence of 1,2,2,6,6-pentamethylpiperidine and PdCl2(PPh3)(2) (1 mol %) in DMF under microwave heating. Short reaction times and high yields have been demonstrated on a variety of substrates.