2-(S)-isocyanomethylpyrrolidine-1-carboxylic acid tert-butyl ester | 1245908-97-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2-(S)-isocyanomethylpyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: (S)-2-Isocyanomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester；tert-butyl (2S)-2-(isocyanomethyl)pyrrolidine-1-carboxylate
• CAS: 1245908-97-7
• 化学式: C₁₁H₁₈N₂O₂
• 分子量: 210.276
• InChiKey: RHJWPRSOYYDGJX-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  33.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(S)-isocyanomethylpyrrolidine-1-carboxylic acid tert-butyl ester 在 selenium 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到(S)-tert-butyl 2-(isoselenocyanatomethyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Isoselenocyanates derived from Boc/Z-amino acids: synthesis, isolation, characterization, and application to the efficient synthesis of unsymmetrical selenoureas and selenoureidopeptidomimetics

  摘要：

  Isoselenocyanates derived from Boc/Z-amino acids are prepared by the reaction of the corresponding isonitriles with selenium powder in presence of triethylamine at reflux. The utility of these new classes of isoselenocyanates in the preparation of selenoureidodipeptidomimetics possessing both amino as well as carboxy termini has been accomplished. The H-1 NMR analysis confirmed that the protocol involving the conversion of isonitriles to isoselenocyanates and their use as coupling agents in assembling selenour-eido derivatives is free from racemization. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.082
• 作为产物：
  描述：

  (S)-tert-butyl 2-(formamidomethyl)pyrrolidine-1-carboxylate 在 伯吉斯试剂 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到2-(S)-isocyanomethylpyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Isoselenocyanates derived from Boc/Z-amino acids: synthesis, isolation, characterization, and application to the efficient synthesis of unsymmetrical selenoureas and selenoureidopeptidomimetics

  摘要：

  Isoselenocyanates derived from Boc/Z-amino acids are prepared by the reaction of the corresponding isonitriles with selenium powder in presence of triethylamine at reflux. The utility of these new classes of isoselenocyanates in the preparation of selenoureidodipeptidomimetics possessing both amino as well as carboxy termini has been accomplished. The H-1 NMR analysis confirmed that the protocol involving the conversion of isonitriles to isoselenocyanates and their use as coupling agents in assembling selenour-eido derivatives is free from racemization. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.082

文献信息

• Discovery of nonpeptide 3,4-dihydroquinazoline-4-carboxamides as potent and selective sst2 agonists
  作者：Jian Zhao、Shimiao Wang、Sangdon Han、Sun Hee Kim、Ana Karin Kusnetzow、Julie Nguyen、Elizabeth Rico-Bautista、Hannah Tan、Stephen F. Betz、R. Scott Struthers、Yunfei Zhu

  DOI：10.1016/j.bmcl.2020.127391

  日期：2020.9

  Nonpeptide sst2 agonists can provide a new treatment option for patients with acromegaly, carcinoid tumors, and neuroendocrine tumors. Our medicinal chemistry efforts have led to the discovery of novel 3,4-dihy-droquinazoline-4-carboxamides as sst2 agonists. This class of molecules exhibits excellent human sst2 potency and selectivity against sst1, sst3, sst4 and sst5 receptors. Leading compound 3-(3-chloro-5-methylphenyl)-6-(3- fluoro-2-hydroxyphenyl)-N,7-dimethyl-N-[(2S)-pyrrolidin-2-yl]methyl}-3,4-dihydroquinazoline-4-carbox-amide (28) showed no inhibition of major CYP450 enzymes (2C9, 2C19, 2D6 and 3A4) and weak inhibition of the hERG channel.