(2R,5S,1'R,2'R,3'R)-2,5-dihydro-2-isopropyl-5-(2'-ethoxycarbonyl-3'-methylcyclopropyl)-3,6-dimethoxypyrazine | 216164-20-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,5S,1'R,2'R,3'R)-2,5-dihydro-2-isopropyl-5-(2'-ethoxycarbonyl-3'-methylcyclopropyl)-3,6-dimethoxypyrazine
• 英文别名: ethyl (1R,2R,3R)-2-[(2S,5R)-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazin-2-yl]-3-methylcyclopropane-1-carboxylate
• CAS: 216164-20-4
• 化学式: C₁₆H₂₆N₂O₄
• 分子量: 310.393
• InChiKey: QZBQCLYLIRUTLD-VEGXAWMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  69.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,5S,1'R,2'R,3'R)-2,5-dihydro-2-isopropyl-5-(2'-ethoxycarbonyl-3'-methylcyclopropyl)-3,6-dimethoxypyrazine 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以62%的产率得到(1R,2R,3R)-2-((S)-Amino-methoxycarbonyl-methyl)-3-methyl-cyclopropanecarboxylic acid ethyl ester
  参考文献：
  名称：

  Enantioselective synthesis of 2-(3′-alkyl-2′-carboxy cyclopropyl)glycines

  摘要：

  New conformationally restricted glutamate analogues 2-(3'-alkyl-2'-carboxycyclopropyl)glycines (1a-c and 2a-c) were enantioselectively prepared by the addition-elimination reaction of the chiral lithium bislactim ether anion of 3 to racemic 4-alkyl-4-bromobut-2-enoates, (C) 1999 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00333-6
• 作为产物：
  描述：

  ethyl (E)-4-bromopent-2-enoate 、 (R)-2,5-二氢-3,6-二甲氧基-2-异丙基吡嗪 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以20%的产率得到(2R,5S,1'S,2'S,3'S)-2,5-dihydro-2-isopropyl-5-(2'-ethoxycarbonyl-3'-methylcyclopropyl)-3,6-dimethoxypyrazine
  参考文献：
  名称：

  Enantioselective synthesis of 2-(3′-alkyl-2′-carboxy cyclopropyl)glycines

  摘要：

  New conformationally restricted glutamate analogues 2-(3'-alkyl-2'-carboxycyclopropyl)glycines (1a-c and 2a-c) were enantioselectively prepared by the addition-elimination reaction of the chiral lithium bislactim ether anion of 3 to racemic 4-alkyl-4-bromobut-2-enoates, (C) 1999 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00333-6

文献信息

• Cyclopropyl glycine derivatives with pharmaceutical properties
  申请人：LILLY S.A.

  公开号：EP0870760A1

  公开（公告）日：1998-10-14

  A pharmaceutical compound of the formula in which R1 is C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, C3-10 cycloalkyl, C3-10 cycloalkyl-C1-10 alkyl, C3-10 cycloalkyl-C2-10 alkenyl, C3-10 cycloalky-C2-10 alkynyl, optionally substituted phenyl-C1-10 alkyl, optionally substituted phenyl-C2-10 alkenyl, optionally substituted phenyl-C2-10 alkynyl, optionally substituted naphthyl, optionally substituted naphthyl-C1-10 alkyl, C1-10 alkoxy-C1-10 alkyl, C3-10 cycloalkoxy-C1-10 alkyl, optionally substituted heterocyclyl, optionally substituted heterocyclyl-C1-10 alkyl, optionally substituted phenyl fused to C5-10 cycloalkyl, optionally substituted tricyclic, optionally substituted tricyclic-C1-10 alkyl, or [optionally substituted phenyl(CH2)n]2-C1-10 alkyl, where n is 0 or 1 to 4, and R2 is hydrogen or one of the values for R1; or a salt or ester thereof.

  一种药物化合物，其式如下 其中 R1 是 C1-10 烷基、C2-10 烯基、C2-10 炔基、C3-10 环烷基、C3-10 环烷基-C1-10 烷基、C3-10 环烷基-C2-10 烯基、C3-10 环烷基-C2-10 炔基、任选取代的苯基-C1-10 烷基、任选取代的苯基-C2-10 烯基、任选取代的苯基-C2-10 炔基、任选取代的萘基、任选取代的萘基-C1-10 烷基、C1-10烷氧基-C1-10烷基，C3-10环烷氧基-C1-10烷基，任选取代的杂环基，任选取代的杂环基-C1-10烷基，与C5-10环烷基融合的任选取代的苯基，任选取代的三环基，任选取代的三环基-C1-10烷基，或[任选取代的苯基（CH2）n]2-C1-10烷基，其中 n 为 0 或 1 至 4，且 R2 是氢或 R1 的值之一； 或其盐或酯。
• US6172058B1
  申请人：——

  公开号：US6172058B1

  公开（公告）日：2001-01-09
• Enantioselective synthesis of 2-(3′-alkyl-2′-carboxy cyclopropyl)glycines
  作者：Angel Mazón、Concepción Pedregal、William Prowse

  DOI：10.1016/s0040-4020(99)00333-6

  日期：1999.5

  New conformationally restricted glutamate analogues 2-(3'-alkyl-2'-carboxycyclopropyl)glycines (1a-c and 2a-c) were enantioselectively prepared by the addition-elimination reaction of the chiral lithium bislactim ether anion of 3 to racemic 4-alkyl-4-bromobut-2-enoates, (C) 1999 Elsevier Science Ltd, All rights reserved.