(S)-3-Methoxycarbonylmethyl-1-(9-phenyl-9H-fluoren-9-yl)-4-thiophen-2-yl-2,5-dihydro-1H-pyrrole-2-carboxylic acid benzyl ester | 274914-43-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-3-Methoxycarbonylmethyl-1-(9-phenyl-9H-fluoren-9-yl)-4-thiophen-2-yl-2,5-dihydro-1H-pyrrole-2-carboxylic acid benzyl ester
• 英文别名: benzyl (2S)-3-(2-methoxy-2-oxoethyl)-1-(9-phenylfluoren-9-yl)-4-thiophen-2-yl-2,5-dihydropyrrole-2-carboxylate
• CAS: 274914-43-1
• 化学式: C₃₈H₃₁NO₄S
• 分子量: 597.734
• InChiKey: QHALKJIRJZVZRZ-BHVANESWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  84.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-3-Methoxycarbonylmethyl-1-(9-phenyl-9H-fluoren-9-yl)-4-thiophen-2-yl-2,5-dihydro-1H-pyrrole-2-carboxylic acid benzyl ester 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 以87%的产率得到(S)-3-Carboxymethyl-1-(9-phenyl-9H-fluoren-9-yl)-4-thiophen-2-yl-2,5-dihydro-1H-pyrrole-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and pharmacology of new enantiopure Δ 3 -4-arylkainoids

  摘要：

  Seven Delta(3)-4-arylkainoids possessing various 4-position aromatic and heteroaromatic groups were synthesized and their apparent affinities were measured in order to explore the influences of 4-position electron density and stereochemistry on receptor affinity and specificity. Kainoids 1a-f were shown to be selective agonists at the NMDA receptor and the electron rich furanyl and thienyl analogues exhibited the highest affinities. Naphthylkainoid 1g proved to be a nonselective antagonist at the iGluRs. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00093-7
• 作为产物：
  描述：

  2-噻吩硼酸 、 (2S)-benzyl-3-methoxycarbonylmethyl-Δ³-4-triflyloxy-N-(PhF)prolinate 在 四(三苯基膦)钯 、 sodium carbonate 、 lithium chloride 作用下， 以 甲苯 为溶剂， 以80%的产率得到(S)-3-Methoxycarbonylmethyl-1-(9-phenyl-9H-fluoren-9-yl)-4-thiophen-2-yl-2,5-dihydro-1H-pyrrole-2-carboxylic acid benzyl ester
  参考文献：
  名称：

  Synthesis and pharmacology of new enantiopure Δ 3 -4-arylkainoids

  摘要：

  Seven Delta(3)-4-arylkainoids possessing various 4-position aromatic and heteroaromatic groups were synthesized and their apparent affinities were measured in order to explore the influences of 4-position electron density and stereochemistry on receptor affinity and specificity. Kainoids 1a-f were shown to be selective agonists at the NMDA receptor and the electron rich furanyl and thienyl analogues exhibited the highest affinities. Naphthylkainoid 1g proved to be a nonselective antagonist at the iGluRs. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00093-7

文献信息

• Synthesis and pharmacology of new enantiopure Δ 3 -4-arylkainoids
  作者：Dany Rondeau、Patrice Gill、Monique Chan、Kenneth Curry、William D. Lubell

  DOI：10.1016/s0960-894x(00)00093-7

  日期：2000.4

  Seven Delta(3)-4-arylkainoids possessing various 4-position aromatic and heteroaromatic groups were synthesized and their apparent affinities were measured in order to explore the influences of 4-position electron density and stereochemistry on receptor affinity and specificity. Kainoids 1a-f were shown to be selective agonists at the NMDA receptor and the electron rich furanyl and thienyl analogues exhibited the highest affinities. Naphthylkainoid 1g proved to be a nonselective antagonist at the iGluRs. (C) 2000 Elsevier Science Ltd. All rights reserved.