1-benzyl 2-methyl (2S)-4-fluoropyrolidine-1,2-dicarboxylate | 556834-89-0

• 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: 1-benzyl 2-methyl (2S)-4-fluoropyrolidine-1,2-dicarboxylate
• 英文别名: 1-benzyl 2-methyl (2S)-4-fluoropyrrolidine-1,2-dicarboxylate；1-benzyl 2-methyl(2S)-4-fluoropyrrolidine-1,2-dicarboxylate；1-O-benzyl 2-O-methyl (2S)-4-fluoropyrrolidine-1,2-dicarboxylate
• CAS: 556834-89-0
• 化学式: C₁₄H₁₆FNO₄
• 分子量: 281.284
• InChiKey: FDPGMTFRBRCTSR-KIYNQFGBSA-N

物化性质

• 沸点：
  382.9±42.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-benzyl 2-methyl (2S)-4-fluoropyrolidine-1,2-dicarboxylate 在 sodium hydroxide 、 水 、 盐酸 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 cis-N-carbobenzyloxy-4-fluoro-L-proline
  参考文献：
  名称：

  1,3-Dihydro-2H-Indole-2-One Compound and Pyrrolidine-2-One Compound Fused With Aromatic Heterocycle

  摘要：

  旨在提供一种对与精氨酸加压素V1b受体相关的病理状况具有疗效的药物。更具体地说，旨在提供一种对抑郁症、焦虑症、阿尔茨海默病、帕金森病、亨廷顿舞蹈症、进食障碍、高血压、消化系统疾病、药物成瘾、癫痫、脑梗死、脑缺血、脑水肿、头部损伤、炎症、免疫疾病、脱发等具有治疗或预防作用的药物。经过深入研究，发现了一种新颖的1,3-二氢-2H-吲哚-2-酮化合物和与杂芳环融合的吡咯烷-2-酮化合物，它们是高度选择性的精氨酸加压素V1b受体拮抗剂，具有高代谢稳定性，表现出有利的血脑屏障穿透和高血浆浓度，从而实现了上述目标。

  公开号：

  US20080318923A1
• 作为产物：
  描述：

  N-CBZ-顺式-L-羟脯氨酸甲酯 在 N,N-二乙基-1,1,2,3,3,3-六氟丙胺 、 diethyl-(pentafluoro-propenyl)-amine 、 sodium fluoride 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 1-benzyl 2-methyl (2S)-4-fluoropyrolidine-1,2-dicarboxylate
  参考文献：
  名称：

  EP1659121

  摘要：

  公开号：

文献信息

• Process for producing fluoro-compounds
  申请人：Kondo Norihisa

  公开号：US20090030228A1

  公开（公告）日：2009-01-29

  The present invention provides a process for producing highly pure fluoro-compounds by making use of less costly and readily handleable N-(2-chloro-1,1,2-trifluoroethyl)diethylamine. The process produces little or no chlorinated by-products. Specifically the present invention provides a process for producing a fluoro-compound, comprising fluorinating an alcohol derivative represented by the following general formula (1): R 1 R 2 R 3 COH  (1) (wherein R 1 represents a hydrogen atom, a substituted or unsubstituted alkyl group, aryl group, alkylcarbonyl group, alkoxycarbonyl group, arylcarbonyl group or aryloxycarbonyl group; and R 2 and R 3 are each independently a substituted or unsubstituted alkyl group, aryl group, alkylcarbonyl group, alkoxycarbonyl group, arylcarbonyl group or aryloxycarbonyl group, wherein at least two of R 1 , R 2 and R 3 may together form part of a ring structure, either with or without a heteroatom) with N,N-diethyl-2-chloro-1,1,2-trifluoroethylamine to form a fluoro-compound represented by the following general formula (2): R 1 R 2 R 3 CF  (2) (wherein R 1 , R 2 and R 3 are as defined above), the process being characterized in that an alcohol derivative represented by the following general formula (3): R 4 OH  (3) (wherein R 4 represents a substituted or unsubstituted alkyl group or aryl group) is added to the reaction system.

  本发明提供了一种利用成本较低且易于处理的N-(2-氯-1,1,2-三氟乙基)二乙胺生产高纯度氟化合物的方法。该方法几乎不产生氯化副产物。具体而言，本发明提供了一种生产氟化合物的方法，包括将由下述通式(1)表示的醇衍生物进行氟化：R1R2R3COH (其中R1代表氢原子、取代或未取代的烷基、芳基、烷基羰基、烷氧羰基、芳基羰基或芳氧羰基；R2和R3分别独立地代表取代或未取代的烷基、芳基、烷基羰基、烷氧羰基、芳基羰基或芳氧羰基，其中R1、R2和R3中的至少两个可以共同形成环结构，带有或不带有杂原子)与N,N-二乙基-2-氯-1,1,2-三氟乙基胺反应，形成由下述通式(2)表示的氟化合物：R1R2R3CF (其中R1、R2和R3如上所定义)，其特征在于向反应体系中加入由下述通式(3)表示的醇衍生物：R4OH (其中R4代表取代或未取代的烷基或芳基)。
• Inhibitors of dipeptidyl peptidase iv
  申请人：Belyakov Sergei

  公开号：US20050070719A1

  公开（公告）日：2005-03-31

  Novel inhibitors of dipeptidyl peptidase IV (DPP IV), pharmaceutical compositions comprising therapeutically effective amounts of novel inhibitors of DPP IV, and novel methods of treating medical conditions are provided. The novel inhibitors of DPP IV described herein are useful in the treatment of neurological disorders, diabetes, inflammatory disorders such as arthritis, obesity, osteoporosis, and of such other enumerated conditions as can be treated with inhibitors of DPP IV.

  本发明提供了二肽酶IV（DPP IV）的新型抑制剂，包括含有治疗有效量的DPP IV新型抑制剂的制药组合物，以及新型治疗医学状况的方法。本发明所描述的DPP IV新型抑制剂在治疗神经系统疾病、糖尿病、炎症性疾病如关节炎、肥胖症、骨质疏松症以及其他可用DPP IV抑制剂治疗的疾病方面非常有用。
• 1,3-Dihydro-2h-indol-2-one derivative
  申请人：Kumagai Toshihito

  公开号：US20060276449A1

  公开（公告）日：2006-12-07

  A 1,3-dihydro-2H-indol-2-one derivative expressed by Formula 1 (wherein R 1 is a halogen atom, a C 1 to C 4 alkyl group, etc., and R 2 is a hydrogen atom, a halogen atom, etc., or R 2 is in the 6-position of the indol-2-one and R 1 and R 2 join together to form a C 3 to C 6 alkylene group, R 3 is a halogen atom, a hydroxyl group, etc., and R 4 is a hydrogen atom, a halogen atom, a C 1 to C 4 alkyl group, etc., or R 4 is in the 3-position of the phenyl and R 3 and R 4 join together to form a methylenedioxy group, R 5 is a hydrogen atom or a fluorine atom, R 6 is an ethylamino group, a dimethylamino group, etc., R 7 is a C 1 to C 4 alkoxy group, and R 8 is a C 1 to C 4 alkoxy group), or a pharmaceutically acceptable salt of this derivative. This is a novel compound that has antagonistic activity against an aruginine-vasopressin V1b receptor.

  公式1所表示的1,3-二氢吲哚-2-酮衍生物（其中R1是卤素原子、C1到C4烷基等，R2是氢原子、卤素原子等，或R2位于吲哚-2-酮的6位，且R1和R2结合形成C3到C6烷基，R3是卤素原子、羟基等，R4是氢原子、卤素原子、C1到C4烷基等，或R4位于苯环的3位，且R3和R4结合形成亚甲二氧基基团，R5是氢原子或氟原子，R6是乙基氨基基团、二甲基氨基基团等，R7是C1到C4烷氧基基团，R8是C1到C4烷氧基基团），或该衍生物的药学上可接受的盐。这是一种新型化合物，具有对抗arginine-vasopressin V1b受体的拮抗活性。
• 1,3-dihydro-2H-indol-2-one derivative
  申请人：Taisho Pharmaceutical Co., Ltd.

  公开号：US07528124B2

  公开（公告）日：2009-05-05

  A 1,3-dihydro-2H-indol-2-one derivative expressed by Formula 1 (wherein R1 is a halogen atom, a C1 to C4 alkyl group, etc., and R2 is a hydrogen atom, a halogen atom, etc., or R2 is in the 6-position of the indol-2-one and R1 and R2 join together to form a C3 to C6 alkylene group, R3 is a halogen atom, a hydroxyl group, etc., and R4 is a hydrogen atom, a halogen atom, a C1 to C4 alkyl group, etc., or R4 is in the 3-position of the phenyl and R3 and R4 join together to form a methylenedioxy group, R5 is a hydrogen atom or a fluorine atom, R6 is an ethylamino group, a dimethylamino group, etc., R7 is a C1 to C4 alkoxy group, and R8 is a C1 to C4 alkoxy group), or a pharmaceutically acceptable salt of this derivative. This is a novel compound that has antagonistic activity against an aruginine-vasopressin V1b receptor.

  公式1表示的是1,3-二氢吲哚-2-酮衍生物（其中R1是卤素原子、C1至C4烷基等，R2是氢原子、卤素原子等，或者R2位于吲哚-2-酮的6位，R1和R2结合形成C3至C6烷基，R3是卤素原子、羟基等，R4是氢原子、卤素原子、C1至C4烷基等，或者R4位于苯环的3位，R3和R4结合形成甲氧基二氧杂环丙基，R5是氢原子或氟原子，R6是乙基氨基基、二甲基氨基基等，R7是C1至C4烷氧基，R8是C1至C4烷氧基），或该衍生物的药学上可接受的盐。这是一种新型化合物，具有对抗arginine-vasopressin V1b受体的拮抗活性。
• PROCESS FOR PRODUCTION OF FLUOROCOMPOUNDS
  申请人：Tosoh F-Tech, Inc.

  公开号：EP1903021A1

  公开（公告）日：2008-03-26

  The present invention provides a process for producing highly pure fluoro-compounds by making use of less costly and readily handleable N-(2-chloro-1,1,2-trifluoroethyl)diethylamine. The process produces little or no chlorinated by-products. Specifically the present invention provides a process for producing a fluoro-compound, comprising fluorinating an alcohol derivative represented by the following general formula (1):         R1R2R3COH     (1) (wherein R1 represents a hydrogen atom, a substituted or unsubstituted alkyl group, aryl group, alkylcarbonyl group, alkoxycarbonyl group, arylcarbonyl group or aryloxycarbonyl group; and R2 and R3 are each independently a substituted or unsubstituted alkyl group, aryl group, alkylcarbonyl group, alkoxycarbonyl group, arylcarbonyl group or aryloxycarbonyl group, wherein at least two of R1, R2 and R3 may together form part of a ring structure, either with or without a heteroatom) with N,N-diethyl-2-chloro-1,1,2-trifluoroethylamine to form a fluoro-compound represented by the following general formula (2):         R1R2R3CF     (2) (wherein R1, R2 and R3 are as defined above), the process being characterized in that an alcohol derivative represented by the following general formula (3):         R4OH     (3) (wherein R4 represents a substituted or unsubstituted alkyl group or aryl group) is added to the reaction system.

  本发明提供了一种利用成本较低、易于处理的 N-(2-氯-1,1,2-三氟乙基)二乙胺生产高纯度氟化合物的工艺。该工艺几乎不会产生氯化副产品。 具体地说，本发明提供了一种生产氟化合物的工艺，包括对由下式通式（1）代表的醇衍生物进行氟化处理： R1R2R3COH (1) (其中 R1 代表氢原子、取代或未取代的烷基、芳基、烷基羰基、烷氧羰基、芳基羰基或芳氧羰基；和 R2 和 R3 各自独立地为取代或未取代的烷基、芳基、烷基羰基、烷氧羰基、芳基羰基或芳氧羰基，其中 R1、R2 和 R3 中至少有两个可共同构成环结构的一部分，可带或不带杂原子）与 N，N-二乙基-2-氯-1，1，2-三氟乙胺形成下通式（2）所代表的氟化合物： R1R2R3CF (2) (其中 R1、R2 和 R3 如上定义)，该工艺的特征在于由下式通式(3)代表的醇衍生物： R4OH (3) (其中 R4 代表取代或未取代的烷基或芳基）加入反应体系中。