3-methoxy-5-(4-trifluoromethylphenyl)pent-4-ynal | 574730-46-4

• 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: 3-methoxy-5-(4-trifluoromethylphenyl)pent-4-ynal
• 英文别名: 3-Methoxy-5-[4-(trifluoromethyl)phenyl]pent-4-ynal
• CAS: 574730-46-4
• 化学式: C₁₃H₁₁F₃O₂
• 分子量: 256.224
• InChiKey: LZGFUKMZPCMMGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-methoxy-5-(4-trifluoromethylphenyl)pent-4-ynal 在 [Rh(nbd)((S)-Tol-BINAP)]BF₄ 、 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以34%的产率得到(S)-3-methoxy-2-(4-trifluoromethylbenzylidene)cyclobutanone
  参考文献：
  名称：

  Parallel Kinetic Resolution of 4-Alkynals Catalyzed by Rh(I)/Tol-BINAP:  Synthesis of Enantioenriched Cyclobutanones and Cyclopentenones

  摘要：

  A Rh(I)/(R)-Tol-BINAP catalyst reacts with a racemic mixture of 4-alkynals to selectively furnish a cyclobutanone from the (R)-substrate and a cyclopentenone from the (S)-substrate. This method is noteworthy from several standpoints, including the scarcity of parallel kinetic resolutions (especially those that are catalyzed or that involve carbon-carbon bond formation) and the dearth of catalytic processes that generate enantioenriched cyclobutanones.

  DOI：

  10.1021/ja035489l
• 作为产物：
  描述：

  4-乙炔基-α,α,α-三氟甲苯 在 正丁基锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 生成 3-methoxy-5-(4-trifluoromethylphenyl)pent-4-ynal
  参考文献：
  名称：

  Parallel Kinetic Resolution of 4-Alkynals Catalyzed by Rh(I)/Tol-BINAP:  Synthesis of Enantioenriched Cyclobutanones and Cyclopentenones

  摘要：

  A Rh(I)/(R)-Tol-BINAP catalyst reacts with a racemic mixture of 4-alkynals to selectively furnish a cyclobutanone from the (R)-substrate and a cyclopentenone from the (S)-substrate. This method is noteworthy from several standpoints, including the scarcity of parallel kinetic resolutions (especially those that are catalyzed or that involve carbon-carbon bond formation) and the dearth of catalytic processes that generate enantioenriched cyclobutanones.

  DOI：

  10.1021/ja035489l

文献信息

• Parallel Kinetic Resolution of 4-Alkynals Catalyzed by Rh(I)/Tol-BINAP:  Synthesis of Enantioenriched Cyclobutanones and Cyclopentenones
  作者：Ken Tanaka、Gregory C. Fu

  DOI：10.1021/ja035489l

  日期：2003.7.1

  A Rh(I)/(R)-Tol-BINAP catalyst reacts with a racemic mixture of 4-alkynals to selectively furnish a cyclobutanone from the (R)-substrate and a cyclopentenone from the (S)-substrate. This method is noteworthy from several standpoints, including the scarcity of parallel kinetic resolutions (especially those that are catalyzed or that involve carbon-carbon bond formation) and the dearth of catalytic processes that generate enantioenriched cyclobutanones.