(-)-5-(1-Methyl-5-methylthiopyrrol-2-oyl)-1,2-dihydro-6-methyl-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid | 89567-41-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (-)-5-(1-Methyl-5-methylthiopyrrol-2-oyl)-1,2-dihydro-6-methyl-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid
• 英文别名: 5-(1-methyl-5-methylthio-2-pyrroyl)-1,2-dihydro-6-methyl-3H-pyrrolo-[1,2-a]-pyrrole-1-carboxylic acid；6-methyl-5-(1-methyl-5-methylsulfanylpyrrole-2-carbonyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid
• CAS: 89567-41-9
• 化学式: C₁₆H₁₈N₂O₃S
• 分子量: 318.397
• InChiKey: ATNDSNXDCWPHGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  89.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-5-(1-Methyl-5-methylthiopyrrol-2-oyl)-1,2-dihydro-6-methyl-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid 、 (S)-(-)-1-苯乙醇 生成 [(1S)-1-phenylethyl] 6-methyl-5-(1-methyl-5-methylsulfanylpyrrole-2-carbonyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylate
  参考文献：
  名称：

  HAGMANN, W. K., SYNTH. COMMUN., 1986, 16, N 4, 437-440

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 5-(1-methyl-5-methylthiopyrrol-2-oyl)-1,2-dihydro-6-methyl-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate 生成 (-)-5-(1-Methyl-5-methylthiopyrrol-2-oyl)-1,2-dihydro-6-methyl-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid
  参考文献：
  名称：

  CHANG, M. N.;BIFTU, T.

  摘要：

  DOI：

文献信息

• 5-(Pyrrol-2-oyl)-1,2-dihydro-3H-pyrrolo [1,2-a]pyrrole derivatives as
  申请人：Merck & Co., Inc.

  公开号：US04511724A1

  公开（公告）日：1985-04-16

  Substituted 5-(pyrrol-2-oyl)1,2-dihydropyrrolo[1,2-a]-pyrrole derivatives have been prepared via decarboxylation of the corresponding 1,7-dicarboxylate prepared from condensation of a dialkyl 1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-7-dicarboxylate-7-carboxylic acid with an appropriately substituted 2-pyrroyl chloride, or conversely, an acid chloride of the former bicyclic compounds with a substituted pyrrole. The compounds are analgesic and anti-inflammatory agents of high activities but low ulcerogenic side effects.

  通过将相应的1,7-二羧酸酯（由二烷基1,2-二氢吡咯并[1,2-a]吡咯-1-7-二羧酸-7-羧酸与适当取代的2-吡咯酰氯缩合制备而成）脱羧，制备了取代的5-(吡咯-2-酰基)1,2-二氢吡咯并[1,2-a]吡咯衍生物，或者反过来，用取代的吡咯酸氯与前一种双环化合物的酸氯缩合。这些化合物是具有高活性但低溃疡副作用的镇痛和抗炎药物。
• Resolution of racemic derivatives of
  申请人：Merck & Co., Inc.

  公开号：US04622407A1

  公开（公告）日：1986-11-11

  Racemic mixture of derivatives of 5-(1-methyl-5-methylthiopyrrol-2-oyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole -2-carboxylic acid and analogs were resolved into pure l- or d-isomers via concomitant isomerization and functional crystallization.

  通过同时异构化和功能晶体化，将5-(1-甲基-5-甲硫基吡咯-2-酰基)-1,2-二氢-3H-吡咯并[1,2-a]吡咯-2-羧酸及其类似物的混合物分离成纯的l-或d-异构体。
• New 5-(pyrrol-2-oyl)-1,2-dihydro-3H-pyrrolo(1,2-a)pyrrole derivatives as anti-inflammatory and analgesic agents
  申请人：Merck & Co., Inc.

  公开号：EP0096816A2

  公开（公告）日：1983-12-28

  Substituted 5-(pyrrol-2-oyl)-1,2-dihydro-pyrrolo [1,2-a]-pyrrole derivatives are disclosed having the structural formula: or a pharmaceutically acceptable salt, ester or amide thereof wherein R is, e.g., hydrogen or loweralkyl; R' is hydrogen, loweralkyl or lower haloalkyl; R2Z can be at any available positions and R2 is R; n is 1 to 3; R3 is, e.g., hydroxy or loweralkoxy; Y is, e.g., oxygen, sulfur or H with the proviso that when Y is H, R is not present; Z is, e.g.,-0-,-S-or halo providing that when Z is halo, R is not present. These compounds have been prepared via decarboxylation of the corresponding 1,7-dicarboxylate prepared from condensation of a dialkyl 1,2-dihydro-3H-pyrrolo[1,2-a]-pyrrole-1-7-dicarboxylate 7 carboxylic acid with an appropriately substituted 2-pyrroyl chloride, or conversely, an acid chloride of the former bicyclic compound with a substituted pyrrole. The compounds are analgesic and antiinflammatory agents of high activities but low ulcerogenic side effects.

  公开了结构式如下的取代的 5-(吡咯-2-酰基)-1,2-二氢-吡咯并[1,2-a]-吡咯衍生物： 或其药学上可接受的盐、酯或酰胺 其中 R 是氢或低级烷基； R' 是氢、低级烷基或低级卤代烷基； R2Z 可以位于任何可用位置，R2 是 R； n 为 1 至 3； R3 是羟基或低级烷氧基； Y 是，例如，氧、硫或 H，但当 Y 是 H 时，R 不存在； Z 是，例如-0-、-S-或卤素，但当 Z 为卤素时，R 不存在。这些化合物是由 1,2-二氢-3H-吡咯并[1,2-a]-吡咯-1-7-二甲酸二烷基 7 羧酸与适当取代的 2-吡咯酰氯缩合制备的相应 1,7-二羧酸盐脱羧制备而成，或者相反，由前一种双环化合物的酰氯与取代的吡咯缩合制备而成。这些化合物是镇痛和抗炎药物，活性高，但致溃副作用小。
• Resolution of racemic derivatives of 5-(1-methyl-5-methyl-thiopyrrol-2-oyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-2-carboxylic acid and analogs
  申请人：Merck & Co., Inc.

  公开号：EP0159674A2

  公开（公告）日：1985-10-30

  Racemic mixture of derivatives of 5-(1-methyl-5-methyl- thiopyrrol - 2 - oyl) -1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-2-carboxylic acid and analogs were resolved into pure I-or d-isomers via concomitant isomerization and functional crystallization.

  通过异构化和功能结晶，5-(1-甲基-5-甲基-硫代吡咯-2-基)-1,2-二氢-3H-吡咯并[1,2-a]吡咯-2-羧酸及其类似物的外消旋混合物衍生物被分离成纯净的 I-或 d-异构体。
• HAGMANN, WILLIAM K.
  作者：HAGMANN, WILLIAM K.

  DOI：——

  日期：——