(Z)-2-(hydroxy(4-(trifluoromethyl)phenyl)methyl)-3-(thiophen-3-yl)-1-(4-(trifluoromethyl)phenyl)prop-2-en-1-one | 1184872-86-3

• 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)-2-(hydroxy(4-(trifluoromethyl)phenyl)methyl)-3-(thiophen-3-yl)-1-(4-(trifluoromethyl)phenyl)prop-2-en-1-one
• 英文别名: (Z)-2-[hydroxy-[4-(trifluoromethyl)phenyl]methyl]-3-thiophen-3-yl-1-[4-(trifluoromethyl)phenyl]prop-2-en-1-one
• CAS: 1184872-86-3
• 化学式: C₂₂H₁₄F₆O₂S
• 分子量: 456.408
• InChiKey: INOACWIGYPHCHI-WQRHYEAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  对三氟甲基苯甲醛 、 3-三甲硅基乙炔基噻吩 在 P(PhCH₂NCH₂CH₂)3N 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以68%的产率得到(Z)-2-(hydroxy(4-(trifluoromethyl)phenyl)methyl)-3-(thiophen-3-yl)-1-(4-(trifluoromethyl)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  P(PhCH₂NCH₂CH₂)₃N: An Efficient Lewis Base Catalyst for the Synthesis of Propargylic Alcohols and Morita−Baylis−Hillman Adducts via Aldehyde Alkynylation

  摘要：

  Proazaphosphatrane P(PhCH2NCH2CH2)(3)N (1a) is an efficient catalyst for the addition of aryl trimethylsilyl alkynes to a variety of aromatic, aliphatic, and heterocyclic aldehydes in THF at room temperature. The reaction conditions are mild and employ a low catalyst loading (ca. 5 mol %). Only propargylic alcohols were isolated in good to excellent isolated yields when electron-rich, electron-neutral, heterocyclic, and aliphatic aldehydes were employed, whereas beta-branched Morita-Baylis-Hillman (MBH) type adducts were isolated with electron-deficient aromatic aldehydes after conventional acid hydrolysis of the TMS ether products. Alkynes containing heterocyclic and aromatic groups bearing electron-withdrawing or -donating substituents underwent clean addition to cyclohexanecarboxaldehyde and to electron-rich aromatic aldehydes to give propargylic alcohols in excellent isolated yields. beta-Branched Morita-Baylis-Hillman (MBH) type adducts were isolated when electron-deficient aromatic aldehydes were employed. Reaction pathways to both types of products are proposed.

  DOI：

  10.1021/jo9012332

文献信息

• P(PhCH₂NCH₂CH₂)₃N: An Efficient Lewis Base Catalyst for the Synthesis of Propargylic Alcohols and Morita−Baylis−Hillman Adducts via Aldehyde Alkynylation
  作者：Kuldeep Wadhwa、Venkat Reddy Chintareddy、John G. Verkade

  DOI：10.1021/jo9012332

  日期：2009.9.4

  Proazaphosphatrane P(PhCH2NCH2CH2)(3)N (1a) is an efficient catalyst for the addition of aryl trimethylsilyl alkynes to a variety of aromatic, aliphatic, and heterocyclic aldehydes in THF at room temperature. The reaction conditions are mild and employ a low catalyst loading (ca. 5 mol %). Only propargylic alcohols were isolated in good to excellent isolated yields when electron-rich, electron-neutral, heterocyclic, and aliphatic aldehydes were employed, whereas beta-branched Morita-Baylis-Hillman (MBH) type adducts were isolated with electron-deficient aromatic aldehydes after conventional acid hydrolysis of the TMS ether products. Alkynes containing heterocyclic and aromatic groups bearing electron-withdrawing or -donating substituents underwent clean addition to cyclohexanecarboxaldehyde and to electron-rich aromatic aldehydes to give propargylic alcohols in excellent isolated yields. beta-Branched Morita-Baylis-Hillman (MBH) type adducts were isolated when electron-deficient aromatic aldehydes were employed. Reaction pathways to both types of products are proposed.