(4R)-4-fluoromethyl-1-[(1R)-1-phenylethyl]-2-pyrrolidone | 307976-21-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4R)-4-fluoromethyl-1-[(1R)-1-phenylethyl]-2-pyrrolidone
• 英文别名: (4S)-4-fluoromethyl-1-[(1R)-1-phenylethyl]-2-pyrrolidone；(4S)-4-(fluoromethyl)-1-[(1R)-1-phenylethyl]pyrrolidin-2-one
• CAS: 307976-21-2
• 化学式: C₁₃H₁₆FNO
• 分子量: 221.275
• InChiKey: LOSHCCKMXMTECP-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R)-4-fluoromethyl-1-[(1R)-1-phenylethyl]-2-pyrrolidone 、 氯甲酸乙酯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以85%的产率得到(3S,4S)-3-ethoxycarbonyl-4-fluoromethyl-1-[(1R)-1-phenylethyl]-2-pyrrolidone
  参考文献：
  名称：

  Tri-, tetra-substituted-3-aminopyrrolidine derivative

  摘要：

  提供了一种喹诺酮合成抗菌剂和治疗感染的药物，对革兰氏阳性和革兰氏阴性细菌均表现出广谱和强效的抗菌活性，并且具有很高的安全性。所提供的化合物由以下式（I）表示： 其中R1和R2代表氢原子，或类似物；R3代表含有1至6个碳原子的烷基基团，或类似物；R4和R5独立地代表氢原子，含有1至6个碳原子的烷基基团，或类似物，但R4和R5不同时代表氢原子；或取代基R4和R5一起代表（a）包括由R4和R5共享的碳原子形成螺环结构与吡咯烷环形成螺环结构的3至6成员环结构；R6和R7独立地代表氢原子，含有1至6个碳原子的烷基基团，或类似物；R8代表含有1至6个碳原子的卤代烷基基团，或类似物；X1代表氢原子或卤原子；A代表氮原子或由式（II）表示的基团。

  公开号：

  US20060264428A1

文献信息

• CIS-SUBSTITUTED FLUOROMETHYLPYRROLIDINE DERIVATIVE
  申请人：——

  公开号：US20020072608A1

  公开（公告）日：2002-06-13

  An antibacterial drug having potent antibacterial activities upon various bacteria including resistant strains and high safety is disclosed, which comprises as an active ingredient, quinolone derivatives represented by the following formula (I), its salts or hydrates thereof: 1 wherein R 1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R 2 represents a halogenomethoxyl group or an alkoxyl group, R 3 represents an alkyl group, an alkenyl group, a halogenoalkyl group, a cyclic alkyl group, a heteroaryl group, an alkoxyl group or an alkylamino group, and R 4 represents a hydrogen atom, a phenyl group, an acetoxymethyl group, a pivaloyloxymethyl group, an ethoxycarbonyl group, a choline group, a dimethylaminoethyl group, a 5-indanyl group, a phthalidinyl group, a 5-alkyl-2-oxo-1,3-dioxol-4-ylmethyl group, 3-acetoxy-2-oxobutyl group, an alkyl group, an alkoxylmethyl group or a phenylalkyl group. These substituents may further have additional substituents.

  揭示了一种具有对各种细菌具有强效抗菌活性，包括耐药菌株和高安全性的抗菌药物，其包括以下式(I)所代表的喹诺酮衍生物作为活性成分，其盐或水合物：其中R1代表氢原子或具有1至6个碳原子的烷基基团，R2代表卤代甲氧基基团或烷氧基基团，R3代表烷基基团、烯基基团、卤代烷基基团、环烷基基团、杂环芳基团、烷氧基基团或烷基氨基基团，R4代表氢原子、苯基、乙酰氧甲基基团、戊二酰氧甲基基团、乙氧羰基基团、胆碱基团、二甲氨基乙基基团、5-茚基基团、邻苯二甲酰基基团、5-烷基-2-氧代-1,3-二氧杂环戊-4-基甲基基团、3-乙酰氧基-2-氧代丁基基团、烷基基团、烷氧基甲基基团或苯基烷基基团。这些取代基还可能具有额外的取代基。
• TRI-, TETRA-SUBSTITUTED-3-AMINOPYRROLIDINE DERIVATIVE
  申请人：TAKAHASHI Hisashi

  公开号：US20090253726A1

  公开（公告）日：2009-10-08

  A quinolone synthetic antibacterial agent and a therapeutic agent for an infection which exhibit broad spectrum and strong antibacterial activity for both Gram positive and Gram negative bacteria, and which are also highly safe are provided. The compound provided is represented by formula (I):

  提供了一种喹诺酮合成抗菌剂和治疗感染的药物，具有广谱和强大的抗菌活性，对革兰氏阳性和革兰氏阴性细菌均有作用，并且非常安全。所提供的化合物由式（I）表示。
• Cis-substituted fluoromethylpyrrolidine derivative
  申请人：Daiichi Pharmaceutical Co., Ltd.

  公开号：US06656952B2

  公开（公告）日：2003-12-02

  An antibacterial drug having potent antibacterial activities upon various bacteria including resistant strains and high safety is disclosed, which comprises as an active ingredient, quinolone derivatives represented by the following formula (I), its salts or hydrates thereof: wherein R1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R2 represents a halogenomethoxyl group or an alkoxyl group, R3 represents an alkyl group, an alkenyl group, a halogenoalkyl group, a cyclic alkyl group, a heteroaryl group, an alkoxyl group or an alkylamino group, and R4 represents a hydrogen atom, a phenyl group, an acetoxymethyl group, a pivaloyloxymethyl group, an ethoxycarbonyl group, a choline group, a dimethylaminoethyl group, a 5-indanyl group, a phthalidinyl group, a 5-alkyl-2-oxo-1,3-dioxol-4-ylmethyl group, 3-acetoxy-2-oxobutyl group, an alkyl group, an alkoxylmethyl group or a phenylalkyl group. These substituents may further have additional substituents.

  本发明公开了一种具有强大的抗菌活性，对包括耐药菌株在内的各种细菌具有高安全性的抗菌药物，其包括以下式（I）所表示的喹诺酮衍生物作为活性成分，其盐或水合物：其中R1表示氢原子或具有1至6个碳原子的烷基；R2表示卤代甲氧基基团或烷氧基基团；R3表示烷基、烯基、卤代烷基、环烷基、杂环芳基、烷氧基或烷基氨基基团；R4表示氢原子、苯基、乙酰氧甲基、季戊酰氧甲基、乙氧羰基、胆碱基、二甲基氨基乙基基团、5-吲哚基基团、邻苯二甲酰亚胺基团、5-烷基-2-氧代-1,3-二氧杂环-4-基甲基基团、3-乙酰氧基-2-氧代丁基基团、烷基、烷氧基甲基基团或苯基烷基基团。这些取代基可能进一步具有其他取代基。
• CIS-SUBSTITUTED FLUOROMETHYLPYRROLIDINE DERIVATIVES
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP0995744A1

  公开（公告）日：2000-04-26

  An antibacterial drug having potent antibacterial activities upon various bacteria including resistant strains and high safety is disclosed, which comprises as an active ingredient, quinolone derivatives represented by the following formula (I), its salts or hydrates thereof: wherein R1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R2 represents a halogenomethoxyl group or an alkoxyl group, R3 represents an alkyl group, an alkenyl group, a halogenoalkyl group, a cyclic alkyl group, a heteroaryl group, an alkoxyl group or an alkylamino group, and R4 represents a hydrogen atom, a phenyl group, an acetoxymethyl group, a pivaloyloxymethyl group, an ethoxycarbonyl group, a choline group, a dimethylaminoethyl group, a 5-indanyl group, a phthalidinyl group, a 5-alkyl-2-oxo-1,3-dioxol-4-ylmethyl group, 3-acetoxy-2-oxobutyl group, an alkyl group, an alkoxylmethyl group or a phenylalkyl group. These substituents may further have additional substituents.

  本发明公开了一种对包括耐药菌株在内的各种细菌具有强效抗菌活性且安全性高的抗菌药，其活性成分包括下式(I)代表的喹诺酮衍生物、其盐类或水合物： 其中 R1 代表氢原子或具有 1 至 6 个碳原子的烷基、 R2 代表卤代甲氧基或烷氧基、 R3 代表烷基、烯基、卤代烷基、环烷基、杂芳基、烷氧基或烷基氨基，以及 R4 代表氢原子、苯基、乙酰氧甲基、新戊酰氧甲基、乙氧基羰基、胆碱基、二甲基氨基乙基、5-茚满基、酞丁基、5-烷基-2-氧代-1,3-二氧戊环-4-基甲基、3-乙酰氧基-2-氧代丁基、烷基、烷氧基甲基或苯基烷基。这些取代基可进一步具有其他取代基。
• TRI- OR TETRA-SUBSTITUTED-3-AMINOPYRROLIDINE DERIVATIVES
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP1882689A1

  公开（公告）日：2008-01-30

  A quinolone synthetic antibacterial agent and a therapeutic agent for an infection which exhibit broad spectrum and strong antibacterial activity for both Gram positive and Gram negative bacteria, and which are also highly safe are provided. The compound provided is represented by following formula (I): wherein R1 and R2 represent hydrogen atom, or the like; R3 represents an alkyl group containing 1 to 6 carbon atoms, or the like; R4 and R5 independently represents hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, or the like, with the proviso that R4 and R5 do not simultaneously represent hydrogen atom; or the substituents R4 and R5 together represent (a) a 3- to 6-membered cyclic structure including the carbon atom shared by R4 and R5 to form a spirocyclic structure with the pyrrolidine ring; R6 and R7 independently represents hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, or the like; R8 represents a halogen-substituted alkyl group containing 1 to 6 carbon atoms, or the like; X1 represents hydrogen atom or a halogen atom; A represents nitrogen atom or a moiety represented by formula (II):

  本发明提供了一种喹诺酮类合成抗菌剂和一种治疗感染的药物，对革兰氏阳性菌和革兰氏阴性菌均具有广谱、强效的抗菌活性，而且安全性高。所提供的化合物由下式(I)表示： 其中 R1 和 R2 代表氢原子或类似物；R3 代表含有 1 至 6 个碳原子的烷基或类似物；R4 和 R5 独立地代表氢原子、含有 1 至 6 个碳原子的烷基或类似物，但 R4 和 R5 不同时代表氢原子；或取代基 R4 和 R5 共同代表 (a) 3 至 6 元环状结构，包括 R4 和 R5 共用的碳原子，与吡咯烷环形成螺环结构；R6 和 R7 独立代表氢原子、含 1 至 6 个碳原子的烷基或类似物；R8 代表含 1 至 6 个碳原子的卤素取代烷基或类似物；X1 代表氢原子或卤素原子；A 代表氮原子或式 (II) 所代表的分子：