t-Butyl 1-[(trifluoromethanesulfonyl)oxy]methylcyclopentanecarboxylate | 174767-44-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: t-Butyl 1-[(trifluoromethanesulfonyl)oxy]methylcyclopentanecarboxylate
• 英文别名: Tert-butyl 1-(trifluoromethylsulfonyloxymethyl)cyclopentane-1-carboxylate
• CAS: 174767-44-3
• 化学式: C₁₂H₁₉F₃O₅S
• 分子量: 332.341
• InChiKey: KEDAOMSXDXQHAE-UHFFFAOYSA-N

物化性质

• 沸点：
  322.7±37.0 °C(Predicted)
• 密度：
  1.299±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  t-Butyl 1-[(trifluoromethanesulfonyl)oxy]methylcyclopentanecarboxylate 在 palladium on activated charcoal N-甲基吗啉 、 盐酸 、 lithium hydroxide 、 氢气 、 N,N'-羰基二咪唑 、 lithium diisopropyl amide 作用下， 以 1,4-二氧六环 、 吡啶 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-2-[(1-{[(R)-1-(2,2-Dimethyl-propionylamino)-2-phenyl-ethyl]-hydroxy-phosphinoylmethyl}-cyclopentanecarbonyl)-amino]-3-(1H-indol-3-yl)-propionic acid
  参考文献：
  名称：

  Design and synthesis of phosphinic acids that triply inhibit endothelin converting enzyme, angiotensin converting enzyme and neutral endopeptidase 24.11

  摘要：

  We have synthesized a series of phosphinic acids as inhibitors of a metalloprotease endothelin converting enzyme (ECE). Potent ECE inhibitors 4g and 4o were identified. These compounds are members of a novel class of ECE inhibitors that are also potent inhibitors of angiotensin converting enzyme and neutral endopeptidase. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00297-1
• 作为产物：
  描述：

  三氟甲磺酸酐 、 t-Butyl 1-(Hydroxymethyl)cyclopentanecarboxylate 以 吡啶 、 二氯甲烷 为溶剂， 以80%的产率得到t-Butyl 1-[(trifluoromethanesulfonyl)oxy]methylcyclopentanecarboxylate
  参考文献：
  名称：

  Design and synthesis of phosphinic acids that triply inhibit endothelin converting enzyme, angiotensin converting enzyme and neutral endopeptidase 24.11

  摘要：

  We have synthesized a series of phosphinic acids as inhibitors of a metalloprotease endothelin converting enzyme (ECE). Potent ECE inhibitors 4g and 4o were identified. These compounds are members of a novel class of ECE inhibitors that are also potent inhibitors of angiotensin converting enzyme and neutral endopeptidase. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00297-1

文献信息

• AMINOPHOSPHINIC DERIVATIVES THAT CAN BE USED IN THE TREATMENT OF PAIN
  申请人：Roques Bernard

  公开号：US20110124601A1

  公开（公告）日：2011-05-26

  The present invention relates to a compound of the following general formula (I): R 1 —NH—CH(R 2 )—P(═O)(OR 3 )—CH 2 —C(R 4 )(R 5 )—CONH—CH(R 6 )—COOR 7 (I) or a pharmaceutically acceptable salt of the latter, an isomer or a mixture of isomers in any proportions, especially a mixture of enantiomers, and in particular a racemic mixture, for which R 1 represents a —C(═O)—O—C(R 8 )(R 9 )—OC(═O)—R 10 group; R 2 represents an optionally substituted hydrocarbon-based chain, an aryl or heteroaryl group or a methylene group substituted by a heterocycle; R 3 represents a hydrogen atom or a —C(R 12 )(R 13 )—OC(═O)—R 14 group; R 4 and R 5 form, together with the carbon that bears them, a saturated hydrocarbon-based ring or an optionally substituted piperidine ring or R 4 represents a hydrogen atom and R 5 represents a phenyl or a benzyl that is optionally substituted, a heteroaromatic ring or a methylene group substituted by a heterocycle; R 6 represents an optionally substituted hydrocarbon-based chain or a phenyl or a benzyl that is optionally substituted; and R 7 represents a hydrogen atom or a benzyl, alkyl, heteroaryl, alkylheteroaryl, —CHMe—COOR 18 , —CHR 19 —OC(═O)OR 20 and —CHR 19 —OC(═O)OR 20 group. The present invention also relates to the use of these compounds as a medicinal product, and in particular for the treatment of pain, more advantageously neuropathic and neuroinflammatory pain, to their method of synthesis and also to the compositions containing them.

  本发明涉及以下通式（I）的化合物：R1—NH—CH（R2）—P（═O）（OR3）—CH2—C（R4）（R5）—CONH—CH（R6）—COOR7或其药学上可接受的盐、异构体或任意比例的异构体混合物，特别是对映体混合物，尤其是外消旋混合物，其中R1代表—C（═O）—O—C（R8）（R9）—OC（═O）—R10基团；R2代表可选取代的碳氢链、芳基或杂环芳基基团或被杂环取代的亚甲基基团；R3代表氢原子或—C（R12）（R13）—OC（═O）—R14基团；R4和R5与承载它们的碳原子一起形成饱和碳氢基环或可选取代的哌啶环或R4代表氢原子，R5代表可选取代的苯基或苄基、杂环芳基环或被杂环取代的亚甲基基团；R6代表可选取代的碳氢链或可选取代的苯基或苄基；R7代表氢原子或苄基、烷基、杂环芳基、烷基杂环芳基、—CHMe—COOR18、—CHR19—OC（═O）OR20和—CHR19—OC（═O）OR20基团。本发明还涉及这些化合物作为药物的用途，特别是用于疼痛治疗，更有利的是神经病理性和神经炎性疼痛的治疗，以及它们的合成方法和含有它们的组合物。
• Aminophosphinic derivatives that can be used in the treatment of pain
  申请人：PHARMALEADS

  公开号：US10131681B2

  公开（公告）日：2018-11-20

  The present invention relates to a compound of the following general formula (I): R1—NH—CH(R2)—P(═O)(OR3)—CH2—C(R4)(R5)—CONH—CH(R6)—COOR7 (I) or a pharmaceutically acceptable salt of the latter, an isomer or a mixture of isomers in any proportions, especially a mixture of enantiomers, and in particular a racemic mixture, for which R1 represents a —C(═O)—O—C(R8)(R9)—OC(═O)—R10 group; R2 represents an optionally substituted hydrocarbon-based chain, an aryl or heteroaryl group or a methylene group substituted by a heterocycle; R3 represents a hydrogen atom or a —C(R12)(R13)—OC(═O)—R14 group; R4 and R5 form, together with the carbon that bears them, a saturated hydrocarbon-based ring or an optionally substituted piperidine ring or R4 represents a hydrogen atom and R5 represents a phenyl or a benzyl that is optionally substituted, a heteroaromatic ring or a methylene group substituted by a heterocycle; R6 represents an optionally substituted hydrocarbon-based chain or a phenyl or a benzyl that is optionally substituted; and R7 represents a hydrogen atom or a benzyl, alkyl, heteroaryl, alkylheteroaryl, —CHMe-COOR18, —CHR19—OC(═O)R20 and —CHR19—OC(═O)OR20 group. The present invention also relates to the use of these compounds as a medicinal product, and in particular for the treatment of pain, more advantageously neuropathic and neuroinflammatory pain, to their method of synthesis and also to the compositions containing them.

  本发明涉及以下通式(I)的化合物：R1-NH-CH(R2)-P(═O)(OR3)-CH2-C(R4)(R5)-CONH-CH(R6)-COOR7(I)或后者的药学上可接受的盐、异构体或任何比例的异构体混合物，特别是对映体混合物，尤其是外消旋混合物，其中R1代表-C(═O)-O-C(R8)(R9)-OC(═O)-R10基团；R2 代表任选取代的烃基链、芳基或杂芳基或被杂环取代的亚甲基； R3 代表氢原子或-C(R12)(R13)-OC(═O)-R14 基团；R4 和 R5 与含有它们的碳一起形成饱和烃基环或任选取代的哌啶环，或 R4 代表氢原子，R5 代表任选取代的苯基或苄基、杂芳环或被杂环取代的亚甲基；R6 代表任选取代的烃基链或任选取代的苯基或苄基；以及 R7 代表氢原子或苄基、烷基、杂芳基、烷基杂芳基、-CHMe-COR18、-CHR19-OC(═O)R20 和-CHR19-OC(═O)OR20 基团。本发明还涉及这些化合物作为医药产品的用途，特别是用于治疗疼痛，尤其是神经病理性疼痛和神经炎性疼痛，还涉及它们的合成方法以及含有它们的组合物。
• PHOSPHINIC ACID DERIVATIVES
  申请人：SCHERING CORPORATION

  公开号：EP0767794B1

  公开（公告）日：2000-02-02
• US5476847A
  申请人：——

  公开号：US5476847A

  公开（公告）日：1995-12-19
• US8703747B2
  申请人：——

  公开号：US8703747B2

  公开（公告）日：2014-04-22