(2S)-2-(甲氧基甲基)-1-吡咯烷羰基氯化物 | 204580-51-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: (2S)-2-(甲氧基甲基)-1-吡咯烷羰基氯化物
• 英文名称: (S)-2-Methoxymethyl-pyrrolidine-1-carbonyl chloride
• 英文别名: (2s)-2-(Methoxymethyl)-1-pyrrolidinecarbonyl chloride；(2S)-2-(methoxymethyl)pyrrolidine-1-carbonyl chloride
• CAS: 204580-51-8
• 化学式: C₇H₁₂ClNO₂
• 分子量: 177.631
• InChiKey: GBUUCSBPNUWUCC-LURJTMIESA-N

物化性质

• 沸点：
  259.6±9.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-2-(甲氧基甲基)-1-吡咯烷羰基氯化物 在 tetraethylammonium metaperiodate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 3-(2'S-methoxymethyl)pyrrolidinocarbonyl-2-oxa-3-aza-3-bicyclo[2.2.1]hept-2-ene
  参考文献：
  名称：

  New acylnitroso compounds for the asymmetric oxyamination of dienes

  摘要：

  A series of new enantiomerically pure acylnitroso compounds have been prepared and tested as dienophiles for the asymmetric oxyamination of dienes. Very high selectivities were obtained with acylnitroso compounds derived from diphenylmethoxymethyl pyrrolidine 2c, the C-2-symmetric pyrrolidines 2d-e and camphorsultam 2f. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00504-3
• 作为产物：
  描述：

  三光气 、 (2S)-2-(甲氧基甲基)吡咯烷盐酸盐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.33h， 生成 (2S)-2-(甲氧基甲基)-1-吡咯烷羰基氯化物
  参考文献：
  名称：

  Synthesis and Evaluation of Carbamate Prodrugs of a Phenolic Compound

  摘要：

  酚类化合物1的一系列氨基甲酸酯被制备并作为前药在体内进行了评估。每种氨基甲酸酯被口服给予大鼠，并随着时间的推移测量母体化合物1的血浆浓度。我们从1的AUC值和血浆中无氨基甲酸酯存在这两方面来判断哪种氨基甲酸酯适合作为1的前药。口服给予2b后1的AUC值大约是直接给予1的40倍，且2b向1的生物转化非常出色。总体而言，双取代氨基甲酸酯导致1的血浆浓度高于单取代氨基甲酸酯。然而双取代氨基甲酸酯几乎总是被检测到在血浆中存在。因此，我们发现乙氨基甲酸酯衍生物2b在这一系列中显示出最佳的前药特性。

  DOI：

  10.1248/cpb.55.328

文献信息

• THIADIAZOLE DERIVATIVES FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES
  申请人：GRIFFIOEN Gerard

  公开号：US20090054410A1

  公开（公告）日：2009-02-26

  This invention provides specifically substituted 1,2,4-thiadiazole derivatives for use in the treatment of an α-synucleopathy such as Parkinson's disease, diffuse Lewy body disease, traumatic brain injury, amyotrophic lateral sclerosis, Niemann-Pick disease, Hallervorden-Spatz syndrome, Down syndrome, neuroaxonal dystrophy, multiple system atrophy and Alzheimer's disease. This invention also provides various methods for producing such substituted 1,2,4-thiadiazole derivatives.
• US8541406B2
  申请人：——

  公开号：US8541406B2

  公开（公告）日：2013-09-24
• Synthesis and Evaluation of Carbamate Prodrugs of a Phenolic Compound
  作者：Yasushi Igarashi、Erika Yanagisawa、Toshihiro Ohshima、Shuichi Takeda、Masaki Aburada、Ken-ichi Miyamoto

  DOI：10.1248/cpb.55.328

  日期：——

  A series of carbamates of the phenolic compound 1 were prepared and evaluated in vivo as its prodrug. Each carbamate was orally administered to rats, and plasma concentrations of the parent compound 1 were measured with the passage of time. We judged which carbamate was suitable for the prodrug of 1 from both the AUC value of 1 and absence of the carbamate in plasma. The AUC value of 1 after oral administration of 2b was approximately 40-fold higher than that for an administration of 1, and the bioconversion from 2b to 1 was excellent. As a whole, di-substituted carbamates resulted in higher plasma concentrations of 1 than did mono-substituted ones. However di-substituted carbamates were almost always detected in plasma. As a result, we found that the ethycarbamoyl derivative 2b demonstrates the best prodrug property in this series.

  酚类化合物1的一系列氨基甲酸酯被制备并作为前药在体内进行了评估。每种氨基甲酸酯被口服给予大鼠，并随着时间的推移测量母体化合物1的血浆浓度。我们从1的AUC值和血浆中无氨基甲酸酯存在这两方面来判断哪种氨基甲酸酯适合作为1的前药。口服给予2b后1的AUC值大约是直接给予1的40倍，且2b向1的生物转化非常出色。总体而言，双取代氨基甲酸酯导致1的血浆浓度高于单取代氨基甲酸酯。然而双取代氨基甲酸酯几乎总是被检测到在血浆中存在。因此，我们发现乙氨基甲酸酯衍生物2b在这一系列中显示出最佳的前药特性。
• New acylnitroso compounds for the asymmetric oxyamination of dienes
  作者：V. Gouverneur、S.J. McCarthy、C. Mineur、D. Belotti、G. Dive、L. Ghosez

  DOI：10.1016/s0040-4020(98)00504-3

  日期：1998.8

  A series of new enantiomerically pure acylnitroso compounds have been prepared and tested as dienophiles for the asymmetric oxyamination of dienes. Very high selectivities were obtained with acylnitroso compounds derived from diphenylmethoxymethyl pyrrolidine 2c, the C-2-symmetric pyrrolidines 2d-e and camphorsultam 2f. (C) 1998 Elsevier Science Ltd. All rights reserved.