(Z)-1-(4-(methoxycarbonyl)phenyl)-2-((4-(methoxycarbonyl)phenyl)(hydroxy)methyl)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-one | 1184872-87-4

• 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)-1-(4-(methoxycarbonyl)phenyl)-2-((4-(methoxycarbonyl)phenyl)(hydroxy)methyl)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-one
• 英文别名: 4-[(Z)-2-[alpha-Hydroxy-4-(methoxycarbonyl)benzyl]-3-[4-(trifluoromethyl)phenyl]propenoyl]benzoic acid methyl ester；methyl 4-[(Z)-1-hydroxy-2-(4-methoxycarbonylbenzoyl)-3-[4-(trifluoromethyl)phenyl]prop-2-enyl]benzoate
• CAS: 1184872-87-4
• 化学式: C₂₇H₂₁F₃O₆
• 分子量: 498.455
• InChiKey: FZIXGHDVQRMQDF-JCMHNJIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1-[(三甲基硅基)乙炔基]-4-(三氟甲基)苯 、 对甲酰基苯甲酸甲酯 在 P(PhCH₂NCH₂CH₂)3N 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以73%的产率得到(Z)-1-(4-(methoxycarbonyl)phenyl)-2-((4-(methoxycarbonyl)phenyl)(hydroxy)methyl)-3-(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.