4-oxo-4-(4-methoxy-3-methyl-phenyl)-trans-crotonic acid | 861896-80-2

• 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: 4-oxo-4-(4-methoxy-3-methyl-phenyl)-trans-crotonic acid
• 英文别名: 4-Oxo-4-(4-methoxy-3-methyl-phenyl)-trans-crotonsaeure；(E)-4-(4-methoxy-3-methylphenyl)-4-oxobut-2-enoic acid
• CAS: 861896-80-2
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: NMSKZNJJNKOMGX-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-oxo-4-(4-methoxy-3-methyl-phenyl)-trans-crotonic acid 在 sodium tetrahydroborate 、 manganese(ll) chloride 作用下， 以 甲醇 为溶剂， 反应 4.5h， 生成 (2R,4S)-4-hydroxy-4-(4-methoxy-3-methylphenyl)-2-{[(1R)-1-phenylethyl]amino}butanoic acid
  参考文献：
  名称：

  Crystallization-induced asymmetric transformations (CIAT): stereoconvergent acid-catalyzed lactonization of substituted 2-amino-4-aryl-4-hydroxybutanoic acids

  摘要：

  Acid-catalyzed lactonization in dilute hydrochloric acid of N-substituted 2-amino-4-aryl-4-hydroxybutanoic acids with electron donating aryl substituents is stereoconvergent. The stereochemical outcome is controlled by the precipitation of little soluble cis-lactones, starting from both syn-2-amino-4-aryl-4-hydroxybutanoic acids and anti-2-amino-4-aryl-4-hydroxybutanoic acids or their mixtures. A highly diastereoselective two-step sequence (acid-catalyzed lactonization with CIAT process followed by alkaline hydrolysis) for the transformation of syn-3b-d to the corresponding anti-3b-d is reported. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.04.024
• 作为产物：
  描述：

  马来酸酐 、 2-甲基苯甲醚 在 三氯化铝 、 硝基苯 作用下， 生成 4-oxo-4-(4-methoxy-3-methyl-phenyl)-trans-crotonic acid
  参考文献：
  名称：

  Dave; Nargund, Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences and Medicine, 1938, vol. 7/3, p. 191,194

  摘要：

  DOI：

文献信息

• Stereoselective sodium borohydride reduction, catalyzed by manganese(II) chloride, of γ-oxo-α-amino acids. A practical approach to syn-γ-hydroxy-α-amino acids
  作者：Dušan Berkeš、Andrej Kolarovič、František Považanec

  DOI：10.1016/s0040-4039(00)00800-5

  日期：2000.7

  A highly stereoselective reduction of γ-oxo-α-amino acids by sodium borohydride in the presence of a catalytic amount of manganese(II) chloride gives syn-γ-hydroxy-α-amino acids. Enantiomerically pure syn-(2S,4R,1′S)-4-aryl-4-hydroxy-2-(1′-phenylethylamino)butanoic acids form stable gels in methanol.

  在催化量的氯化锰（II）存在下，硼氢化钠可高度立体选择性地还原γ-氧代-α-氨基酸，生成顺式-γ-羟基-α-氨基酸。对映体纯的顺式-（2 S，4 R，1 'S）-4-芳基-4-羟基-2-（1'-苯基乙基氨基）丁酸在甲醇中形成稳定的凝胶。
• SUBSTITUTED 2(5H)FURANONE, 2(5H)THIOPHENONE AND 2(5H)PYRROLONE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS ENDOTHELIN ANTAGONISTS
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0714391A1

  公开（公告）日：1996-06-05