2-(p-chlorophenyl)-2H-chromene-3-carbaldehyde

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(p-chlorophenyl)-2H-chromene-3-carbaldehyde
• 英文别名: 2-(4-chlorophenyl)-2H-chromene-3-carbaldehyde
• 化学式: C₁₆H₁₁ClO₂
• 分子量: 270.715
• InChiKey: XHKVKGKYURPMDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(p-chlorophenyl)-2H-chromene-3-carbaldehyde 、 diethylzinc 在 (S)-2-((S)-1'-phenylethylamino)-1,1,2-triphenylethan-1-ol 作用下， 以 正己烷 、 甲基叔丁基醚 为溶剂， 反应 3.0h， 以89%的产率得到
  参考文献：
  名称：

  Asymmetric Preparation of New N,N-Dialkyl-2-amino-1,1,2-triphenylethanol Catalysts and a Kinetic Resolution in the Addition of Diethylzinc to Flavene-3-carbaldehydes

  摘要：

  Enantiopure N,N-dialkyl-(S)-2-amino-1,1,2-triphenylethanols were prepared using a new synthetic methodology and tested for their ability to catalyze the enantioselective addition of diethylzinc to aldehydes. The structural modification of N- substituents of the catalysts led us to identify N- methyl- N-(S)-1-phenylethyl-substituted 4d as an effective catalyst for the addition. Also disclosed is a kinetic resolution of racemic flavene-3-carbaldehydes with the chiral catalyst.

  DOI：

  10.1055/s-0032-1318301
• 作为产物：
  描述：

  4-chlorocinnamaldehyde 、 水杨醛 在 四氢吡咯 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-(p-chlorophenyl)-2H-chromene-3-carbaldehyde
  参考文献：
  名称：

  Asymmetric Preparation of New N,N-Dialkyl-2-amino-1,1,2-triphenylethanol Catalysts and a Kinetic Resolution in the Addition of Diethylzinc to Flavene-3-carbaldehydes

  摘要：

  Enantiopure N,N-dialkyl-(S)-2-amino-1,1,2-triphenylethanols were prepared using a new synthetic methodology and tested for their ability to catalyze the enantioselective addition of diethylzinc to aldehydes. The structural modification of N- substituents of the catalysts led us to identify N- methyl- N-(S)-1-phenylethyl-substituted 4d as an effective catalyst for the addition. Also disclosed is a kinetic resolution of racemic flavene-3-carbaldehydes with the chiral catalyst.

  DOI：

  10.1055/s-0032-1318301

文献信息

• One-Pot Pyrrolidine-Catalyzed Synthesis of Benzopyrans, Benzothiopyranes, and Dihydroquinolidines
  作者：Ismail Ibrahem、Henrik Sundén、Ramon Rios、Gui-Ling Zhao、Armando Córdova

  DOI：10.2533/chimia.2007.219

  日期：——

  A simple catalytic racemic synthesis of benzopyranes, benzothiopyranes and 1,2-dihydroquinolines is presented. The organocatalytic domino reactions between 2-heteroatom substituted aldehyde derivatives and ?,?-unsaturated aldehydes or ?,?-unsaturated cyclic ketones proceed with excellent chemoselectivity to give the corresponding products in good to high yields.

  介绍了一种简单的催化不对称合成苯并吡喃、苯并噻吩和1,2-二氢喹啉的方法。2-杂原子取代的醛衍生物与α，β-不饱和醛或α，β-不饱和环状酮之间的有机催化多米诺反应具有良好的化学选择性，产物收率在良好到高收率之间。
• Asymmetric Preparation of New N,N-Dialkyl-2-amino-1,1,2-triphenylethanol Catalysts and a Kinetic Resolution in the Addition of Diethylzinc to Flavene-3-carbaldehydes
  作者：Yong Park、Seock Kang、Jinho Baek、Yi Ko、Chan Im

  DOI：10.1055/s-0032-1318301

  日期：——

  Enantiopure N,N-dialkyl-(S)-2-amino-1,1,2-triphenylethanols were prepared using a new synthetic methodology and tested for their ability to catalyze the enantioselective addition of diethylzinc to aldehydes. The structural modification of N- substituents of the catalysts led us to identify N- methyl- N-(S)-1-phenylethyl-substituted 4d as an effective catalyst for the addition. Also disclosed is a kinetic resolution of racemic flavene-3-carbaldehydes with the chiral catalyst.