(2S)-benzyl-3-methoxycarbonylmethyl-Δ³-4-triflyloxy-N-(PhF)prolinate | 163594-20-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2S)-benzyl-3-methoxycarbonylmethyl-Δ³-4-triflyloxy-N-(PhF)prolinate
• 英文别名: benzyl (2S)-3-(2-methoxy-2-oxoethyl)-1-(9-phenylfluoren-9-yl)-4-(trifluoromethylsulfonyloxy)-2,5-dihydropyrrole-2-carboxylate
• CAS: 163594-20-5
• 化学式: C₃₅H₂₈F₃NO₇S
• 分子量: 663.671
• InChiKey: RARIALAAZLHYCK-YTTGMZPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  47
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2S)-benzyl-3-methoxycarbonylmethyl-Δ³-4-triflyloxy-N-(PhF)prolinate 在 sodium hydroxide 、 四(三苯基膦)钯 、 sodium carbonate 、 苯甲醚 、 三氟乙酸 、 lithium chloride 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 甲苯 为溶剂， 生成 (2S)-Δ³-4-Phenylkainic 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：

  N-苯基双(三氟甲烷磺酰)亚胺 、 Benzyl 3-((methoxycarbonyl)methyl)-4-oxo-N-(9-(9-phenylfluorenyl))prolinate 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到(2S)-benzyl-3-methoxycarbonylmethyl-Δ³-4-triflyloxy-N-(PhF)prolinate
  参考文献：
  名称：

  Synthesis of Enantiopure Arylkainoids: Preparation of (2S)-.DELTA.3-4-Phenylkainic Acid

  摘要：

  DOI：

  10.1021/jo00114a007

文献信息

• Synthesis of Enantiopure Arylkainoids: Preparation of (2S)-.DELTA.3-4-Phenylkainic Acid
  作者：Patrice Gill、William D. Lubell

  DOI：10.1021/jo00114a007

  日期：1995.5
• 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.