4-(3-phenyl-allylideneamino)-benzoic acid methyl ester | 890707-31-0

• 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-(3-phenyl-allylideneamino)-benzoic acid methyl ester
• CAS: 890707-31-0
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: ARIPOTIFJUYKCA-XKKIXLAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(3-phenyl-allylideneamino)-benzoic acid methyl ester 在 yttrium(III) trifluoromethanesulfonate 吡啶 、 4-二甲氨基吡啶 、 臭氧 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 27.5h， 生成 (Z)-4-(2-cyano-vinyl)-5-(2,2,2-trifluoro)-2,3,3a,4,5,9b-hexahydro-pyrrolo[3,2-c]quinoline-1,8-dicarboxylic acid 1-benzyl ester 8-methyl ester
  参考文献：
  名称：

  Synthesis of the heterocyclic core of martinelline and martinellic acid

  摘要：

  A Povarov reaction, between an aromatic imine derived from cinnamaldehyde and a cyclic enamide, was employed to rapidly construct the tricyclic core of the alkaloids martinelline and martinellic acid. The cycloaddition was completely regioselective though the exolendo selectivity was poor. The diastercoisomers were readily separated by flash chromatography and the relative stereochemistry of the exo-isomer confirmed by single crystal X-ray crystallography. This intermediate was converted to the central core of the aforementioned alkaloids in five additional synthetic operations. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.02.029
• 作为产物：
  描述：

  反式肉桂醛 、 4-氨基苯甲酸甲酯 在 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以90%的产率得到4-(3-phenyl-allylideneamino)-benzoic acid methyl ester
  参考文献：
  名称：

  Synthesis of the heterocyclic core of martinelline and martinellic acid

  摘要：

  A Povarov reaction, between an aromatic imine derived from cinnamaldehyde and a cyclic enamide, was employed to rapidly construct the tricyclic core of the alkaloids martinelline and martinellic acid. The cycloaddition was completely regioselective though the exolendo selectivity was poor. The diastercoisomers were readily separated by flash chromatography and the relative stereochemistry of the exo-isomer confirmed by single crystal X-ray crystallography. This intermediate was converted to the central core of the aforementioned alkaloids in five additional synthetic operations. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.02.029

文献信息

• Method for coupling polymers obtained by the anionic polymerization of dienic and/or vinylaromatic monomers
  申请人：ENIRICERCHE S.p.A.

  公开号：EP0212693A1

  公开（公告）日：1987-03-04

  Coupling agents of general formula (Y-CH=CH-CH=N)n-X and/or (Y - CH = CH - N =)n′ - Z and their use in a method for the termination of living polymers obtained by the anionic polymerization of dienic and/or vinylaromatic monomers.

  通式偶联剂 (Y-CH=CH-CH=N)n-X 和/或 (Y-CH=CH-N=)n′-Z 和/或乙烯芳香族单体阴离子聚合得到的活聚合物的终止方法中的应用。
• Synthesis of the heterocyclic core of the alkaloids martinelline and martinellic acid
  作者：Mark Hadden、Mark Nieuwenhuyzen、Daire Osborne、Paul J Stevenson、Norris Thompson

  DOI：10.1016/s0040-4039(01)01267-9

  日期：2001.9

  The tricyclic core of martinelline and martinellic acid was rapidly assembled utilising an imino Diels-Alder reaction of an imine derived from cinnamaldehyde with a cyclic enamide. The cycloaddition was completely regioselective though the exo endo selectivity was poor. These diastercoisomers were readily separated by flash chromatography and the relative stereochemistry of the exo-isomer confirmed by single crystal X-ray crystallography. This intermediate was converted to the central core of the aforementioned alkaloids in five additional synthetic operations. (C) 2001 Elsevier Science Ltd. All rights reserved.
• CIUFOLINI, MARCO A.;SPENCER, GEORGE O., J. ORG. CHEM., 54,(1989) N0, C. 4739-4741
  作者：CIUFOLINI, MARCO A.、SPENCER, GEORGE O.

  DOI：——

  日期：——
• US4734461A
  申请人：——

  公开号：US4734461A

  公开（公告）日：1988-03-29