tert-butyl (S)-2-(hydroxymethyl)aziridine-1-carboxylate | 1198080-11-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丙烷
• 英文名称: tert-butyl (S)-2-(hydroxymethyl)aziridine-1-carboxylate
• 英文别名: (S)-N-Boc-2-(hydroxymethyl)aziridine；(S)-tert-butyl 2-(hydroxymethyl)aziridine-1-carboxylate；tert-butyl (2S)-2-(hydroxymethyl)aziridine-1-carboxylate
• CAS: 1198080-11-3
• 化学式: C₈H₁₅NO₃
• 分子量: 173.212
• InChiKey: CFIQLGGGUSYWKT-AADKRJSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  49.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-2-(hydroxymethyl)aziridine-1-carboxylate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二异丙胺 、 三苯基膦 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 82.0h， 生成 (S)-tert-butyl 2-((5-ethynylpyridin-3-yloxy)methyl)azetidine-1-carboxylate
  参考文献：
  名称：

  Design, Synthesis and Discovery of Picomolar Selective α4β2 Nicotinic Acetylcholine Receptor Ligands

  摘要：

  Developing novel and selective compounds that desensitize alpha 4 beta 2 nicotinic acetylcholine receptors (nAChRs) could provide new effective treatments for nicotine addiction, as well as other disorders. Here we report a new class of nAChR ligands that display high selectivity and picomolar binding affinity for alpha 4 beta 2 nicotinic receptors. The novel compounds have K-i; values in the range of 0.031-0.26 nM and properties that should make them good candidates as drugs acting in the CNS. The selected lead compound 1 (VMY-2-95) binds with high affinity and potently desensitizes alpha 4 beta 2 nAChRs. At a dose of 3 mg/kg, compound 1 significantly reduced rat nicotine self-administration. The overall results support further characterizations of compound 1 and its analogues in preclinical models of nicotine addiction and perhaps other disorders involving nAChRs.

  DOI：

  10.1021/jm4008455
• 作为产物：
  描述：

  tert-butyl (S)-2-formylaziridine-1-carboxylate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 tert-butyl (S)-2-(hydroxymethyl)aziridine-1-carboxylate
  参考文献：
  名称：

  Enantioselective aziridination reaction of α,β-unsaturated aldehydes using an organocatalyst and tert-butyl N-arenesulfonyloxycarbamates

  摘要：

  An organocatalytic enantioselective aziridination reaction of alpha,beta-unsaturated aldehydes including aromatic substrates using N-arenesulfonyloxycarbamates in the presence of diphenylprolinol triethylsilyl ether and sodium carbonate or sodium acetate is described.

  DOI：

  10.1016/j.tetlet.2009.02.095

文献信息

• 一种LZC696中间体及其合成方法
  申请人：上海博氏医药科技有限公司

  公开号：CN105237560B

  公开（公告）日：2018-07-06

  本发明公开了一种化合物，所述化合物为(R)‑叔丁基(1‑((1,1’联苯)‑4‑基)3‑((叔丁基二甲基硅基)氧)丙烷‑2‑基)氨基甲酸酯，其结构式如式A所示：A。采用这种化合物合成LZC696中间体，整个工艺过程没有昂贵的试剂和原料，无对氧气敏感反应，纯化程序简单，只需要在化合物3和最终产品重结晶纯化就可以达到商业化使用纯度。本发明合成工艺成本低，简单环保，适合工业化放量生产。
• Asymmetric Total Syntheses of (−)-Renieramycin M and G and (−)-Jorumycin Using Aziridine as a Lynchpin
  作者：Yan-Chao Wu、Jieping Zhu

  DOI：10.1021/ol9024919

  日期：2009.12.3

  By exploring the triple reactivity of two aziridines and double nucleophilicity of two aromatics, convergent and versatile syntheses of the above four natural products were developed.
• Enantioselective aziridination reaction of α,β-unsaturated aldehydes using an organocatalyst and tert-butyl N-arenesulfonyloxycarbamates
  作者：Hiromi Arai、Naomi Sugaya、Neri Sasaki、Kazuishi Makino、Sylvain Lectard、Yasumasa Hamada

  DOI：10.1016/j.tetlet.2009.02.095

  日期：2009.7

  An organocatalytic enantioselective aziridination reaction of alpha,beta-unsaturated aldehydes including aromatic substrates using N-arenesulfonyloxycarbamates in the presence of diphenylprolinol triethylsilyl ether and sodium carbonate or sodium acetate is described.
• Design, Synthesis and Discovery of Picomolar Selective α4β2 Nicotinic Acetylcholine Receptor Ligands
  作者：Venkata M. Yenugonda、Yingxian Xiao、Edward D. Levin、Amir H. Rezvani、Thao Tran、Nour Al-Muhtasib、Niaz Sahibzada、Teresa Xie、Corinne Wells、Susan Slade、Joshua E. Johnson、Sivanesan Dakshanamurthy、Hye-Sik Kong、York Tomita、Yong Liu、Mikell Paige、Kenneth J. Kellar、Milton L. Brown

  DOI：10.1021/jm4008455

  日期：2013.11.14

  Developing novel and selective compounds that desensitize alpha 4 beta 2 nicotinic acetylcholine receptors (nAChRs) could provide new effective treatments for nicotine addiction, as well as other disorders. Here we report a new class of nAChR ligands that display high selectivity and picomolar binding affinity for alpha 4 beta 2 nicotinic receptors. The novel compounds have K-i; values in the range of 0.031-0.26 nM and properties that should make them good candidates as drugs acting in the CNS. The selected lead compound 1 (VMY-2-95) binds with high affinity and potently desensitizes alpha 4 beta 2 nAChRs. At a dose of 3 mg/kg, compound 1 significantly reduced rat nicotine self-administration. The overall results support further characterizations of compound 1 and its analogues in preclinical models of nicotine addiction and perhaps other disorders involving nAChRs.