帕拉米韦杂质41 | 251327-00-1

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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
• 中文名称: 帕拉米韦杂质41
• 英文名称: methyl (4S)-4-[(tert-butyloxycarbonyl)amino]cyclopent-1-ene-1-carboxylate
• 英文别名: (4S)-4-tert-butoxycarbonylaminocyclopent-1-enecarboxylic acid methyl ester；methyl (4S)-4-{[(tert-butoxy)carbonyl]amino}cyclopent-1-ene-1-carboxylate；methyl (4S)-4-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentene-1-carboxylate
• CAS: 251327-00-1
• 化学式: C₁₂H₁₉NO₄
• 分子量: 241.287
• InChiKey: BPVUUOLKMLXVJR-VIFPVBQESA-N

物化性质

• 沸点：
  340.6±42.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

制备方法与用途

本品为帕拉米韦的杂质，主要用于作为标准品和对照品。

反应信息

• 作为反应物：
  描述：

  帕拉米韦杂质41 在 盐酸 、 溶剂黄146 作用下， 反应 1.0h， 以77%的产率得到(+)-(4S)-4-aminocyclopent-1-ene-1-carboxylic acid
  参考文献：
  名称：

  Inhibition and Substrate Activity of Conformationally Rigid Vigabatrin Analogues with γ-Aminobutyric Acid Aminotransferase

  摘要：

  Several cyclopentene GABA analogues were synthesized as conformationally rigid analogues of the epilepsy drug vigabatrin and tested as inhibitors and substrates of gamma-aminobutyric acid aminotransferase (GABA-AT). None of these compounds produced time-dependent inhibition. (1R,4S)-(+)-4-Amino-2-cyclopentene-1-carboxylic acid ((+)-3), (4R)-(-)-4-amino-1-cyclopentene-1-carboxylic acid ((-)-4), and d,l-3-amino-1-cyclopentene-1-carboxylic acid (6) are good substrates. The K-m and k(cat) values far the latter two compounds are very similar to those of GABA, suggesting that they bind in an orientation similar to that of GABA. The K-m value for (+)-3 is 24 times lower than that for GABA, although its k(cat) value is only one-fourth that for GABA; nonetheless, it is a better substrate for GABA-AT than is GABA. All of these compounds, as well as the enantiomers of 3 and 4 and d,l-trans-4-amino-2-cyclopentene-1-carboxylic acid (5), are competitive inhibitors of GABA-AT. These results demonstrate the effects of the carboxylate group orientation and the stereochemistry of the amino and carboxylate groups on the substrate activity and inhibitor activity, and this should be important to the future design of inhibitors of GABA-AT.

  DOI：

  10.1021/jm990271o
• 作为产物：
  描述：

  (1S,4R)-4-甲基环戊-2-烯甲酸甲酯盐酸盐 在 TEA 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 74.0h， 生成 帕拉米韦杂质41
  参考文献：
  名称：

  对映纯4-（叔丁氧基羰基氨基）环戊-1-烯羧酸甲酯的高选择性定向氢化

  摘要：

  同时使用的ñ -叔叔丁氧羰和羟基定向加氢方法得到的3-基本上单非对映体（叔丁氧基羰基）-4- hydroxycyclopentanecarboxylic酸甲酯和3-（叔丁氧基羰基）环戊烷羧酸甲酯进行说明。这些结果结合了第一个报道的官能化环戊烯的氨基甲酸酯定向加氢反应。

  DOI：

  10.1016/s0040-4039(00)02210-3

文献信息

• Substituted cyclopentenes, their preparation and their use for chiral scaffolds
  申请人：ChirotechTechnology Limited

  公开号：US06593489B1

  公开（公告）日：2003-07-15

  3,4-Disubstituted-1-cyclopentene compounds, in substantially enantiopure form, have the relative stereochemistry according to formula (1A) or (1B) including the opposite enantiomers thereof, wherein R1 is either COOX, wherein X is selected from the group consisting of alkyl, H, and a salt-forming cation, or CH2OH, whererin the hydroxy group is optionally protected; R2 is H or a protecting group; R3 is H or alkyl, and R4 is selected from the group consisting of H, alkoxy, alkyl, aryl, and aralkyl; or, in the case of formula (1A), R2 and R4 are linked to form an oxazolidonone ring. These compounds can be used to prepare a series of complementary stereochemcially varied cyclopentane scaffolds.

  3,4-二取代-1-环戊烯化合物，在基本对映纯形式下，具有相对立体化学结构，符合式（1A）或（1B），包括其相反对映异构体，其中R1为COOX，其中X选自烷基、H和形成盐的阳离子组成的群；或CH2OH，其中羟基可选地被保护；R2为H或保护基；R3为H或烷基；R4选自H、烷氧基、烷基、芳基和芳基烷基组成的群；或者在式（1A）的情况下，R2和R4连接形成噁唑烷酮环。这些化合物可用于制备一系列互补的立体化学变化的环戊烷支架。
• [EN] SUBSTITUTED CYCLOPENTENES, THEIR PREPARATION AND THEIR USE FOR CHIRAL SCAFFOLDS<br/>[FR] CYCLOPENTENES SUBSTITUES, LEUR PREPARATION ET LEUR UTILISATION POUR DES OSSATURES CHIRALES
  申请人：CHIROTECH TECHNOLOGY LTD

  公开号：WO2001017952A1

  公开（公告）日：2001-03-15

  3,4-Disubstituted-1-cyclopentene compounds, in substantially enantiopure form, have the relative stereochemistry according to formula (1A) or (1B) including the opposite enantiomers thereof, wherein R1 is either COOX, wherein X is alkyl, H or a salt-forming cation, or CH¿2?OH, wherein the hydroxyl group is optionally protected; R?2¿ is H or a protecting group; R3 is H or alkyl; and R4 is H, alkoxy, alkyl, aryl or aralkyl; or, in the case of formula 1A, R?2 and R4¿ are linked to form an oxazolidinone ring. These compounds can be used to prepare a series of complementary stereochemically varied cyclopentane scaffolds.

  3,4-二取代-1-环戊烯化合物，其绝大部分为对映体纯形式，具有相对立体化学式(1A)或(1B)，包括其相反对映体，其中R1为COOX，其中X为烷基，氢或形成盐的阳离子，或CH2OH，其中羟基可选地被保护；R2为氢或保护基；R3为氢或烷基；R4为氢，烷氧基，烷基，芳基或芳基烷基；或者，在公式1A的情况下，R2和R4结合形成噁唑烷酮环。这些化合物可用于制备一系列互补的立体化学变化的环戊烷支架。
• [EN] PRODUCTION OF TRANS-4-AMINOCYCLOPENT-2-ENE-1-CARBOXYLIC ACID DERIVATIVES<br/>[FR] PRODUCTION DE DÉRIVÉS D'ACIDE TRANS-4-AMINOCYCLOPENT-2-ÈNE-1-CARBOXYLIQUE
  申请人：REDDYS LAB LTD DR

  公开号：WO2011003061A3

  公开（公告）日：2011-05-05
• SUBSTITUTED CYCLOPENTENES, THEIR PREPARATION AND THEIR USE FOR CHIRAL SCAFFOLDS
  申请人：Chirotech Technology Limited

  公开号：EP1210324B1

  公开（公告）日：2004-03-31
• PRODUCTION OF TRANS-4-AMINOCYCLOPENT-2-ENE-1-CARBOXYLIC ACID DERIVATIVES
  申请人：Dr. Reddy's Laboratories, Ltd.

  公开号：EP2448916B1

  公开（公告）日：2014-09-03