benzyl 2-methylaziridine-1-carboxylate | 946088-68-2

• 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: benzyl 2-methylaziridine-1-carboxylate
• 英文别名: (S)-Benzyl 2-methylaziridine-1-carboxylate；benzyl (2S)-2-methylaziridine-1-carboxylate
• CAS: 946088-68-2
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: LUBRSMFTXSITMJ-QHGLUPRGSA-N

物化性质

• 沸点：
  289.1±19.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  benzyl 2-methylaziridine-1-carboxylate 在 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 (S)-2-甲基氮丙啶
  参考文献：
  名称：

  Scalable Synthesis of N-Acylaziridines from N-Tosylaziridines

  摘要：

  N-Acylaziridines are important starting materials for the synthesis of chiral amine derivatives. The traditional methods for producing these activated aziridines have significant drawbacks. The gram scale synthesis of N-acylaziridines by deprotection of N-tosylaztridines and reprotection with N-hydroxysuccinimide derivatives is described. Mono- and disubstituted aziridines perform well, with complete retention of stereochemical purity. The consistently moderate yields are linked to the N-tosylaziridine deprotection step, while acylation with N-hydroxysuccinimide derivatives is highly efficient.

  DOI：

  10.1021/jo401267j
• 作为产物：
  描述：

  N-苄氧基羰基-L-丙氨醇 在 氢氧化钾 、 对甲苯磺酰氯 作用下， 以 乙醚 为溶剂， 生成 benzyl 2-methylaziridine-1-carboxylate
  参考文献：
  名称：

  Comparative approaches toward diamines containing spatially separated homobenzylic and benzylic nitrogen stereocenters

  摘要：

  Several synthetic strategies to diamines 1-3 are described. The optimum approach via opening of aziridine afforded 1 3 in 29-60% yield over 3-5 steps. A study on formation of the benzylic stereocenter using Toste's rhenium-catalyzed asymmetric reduction of phosphinyl ketimines was also evaluated and afforded 15 in 92% de. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.073

文献信息

• Stereoselective synthesis of 2,5-disubstituted morpholines using a palladium-catalyzed hydroamination reaction
  作者：Alicia McGhee、Brian M. Cochran、Torrey A. Stenmark、Forrest E. Michael

  DOI：10.1039/c3cc44117b

  日期：——

  A palladium-catalyzed hydroamination reaction is the key step in a stereoselective synthesis of 2,5-disubstituted and 2,3,5-trisubsituted morpholines from carbamate-protected aziridines. Aziridines are selectively attacked at the more substituted position by unsaturated alcohol nucleophiles using Lewis acid catalysts. Palladium-catalyzed hydroamination of the resulting aminoalkenes gives morpholines

  钯催化的加氢胺化反应是从氨基甲酸酯保护的氮丙啶立体选择性合成2，5-二取代和2,3,5-三取代吗啉的关键步骤。使用路易斯酸催化剂，不饱和醇亲核试剂选择性地在更取代的位置上攻击氮丙啶。所得氨基烯烃的钯催化加氢胺化反应可将吗啉作为单一非对映异构体以极佳的收率得到。
• METHOD FOR PREPARING DIPEPTIDYL PEPTIDASE-IV INHIBITOR AND INTERMEDIATE
  申请人：Kwak Woo Young

  公开号：US20120016125A1

  公开（公告）日：2012-01-19

  The present invention relates to an improved method for preparing dipeptidyl peptidase-IV inhibitor and intermediate. The present invention is able to reduce preparation costs by using low cost reagents on reaction and is able to be used in mass production by improving yield.

  本发明涉及一种改进的制备二肽基肽酶-IV抑制剂和中间体的方法。本发明能够通过在反应中使用低成本试剂来降低制备成本，并且通过提高产率能够用于大规模生产。
• Synthesis of novel N-protected β3-amino nitriles: study of their hydrolysis involving a nitrilase-catalyzed step
  作者：Maité Sylla-Iyarreta Veitía、Pierre Louis Brun、Pierre Jorda、Annie Falguières、Clotilde Ferroud

  DOI：10.1016/j.tetasy.2009.07.045

  日期：2009.9

  Several commercially available nitrilases were investigated with regard to their potential to hydrolyze N-protected beta(3)-amino nitriles into their corresponding N-protected beta(3)-amino acids.The biotransformations were obtained in different proportions depending oil the nitrilase involved The best hydrolysis results were achieved for the N-Cbz-beta(3)-amino nitrile from i-alanine using the NIT-107, in a phosphate buffer at 0 05 M However, no biotransformation into the corresponding acids was observed for the N-sulfonylamide beta(3)-amino nitriles. Two simple and efficient procedures to prepare the beta(3)-amino nitriles from their analogous alpha-amino acids are described Thirty four new substances were synthesized and characterized over the course of this work. (C) 2009 Elsevier Ltd All rights reserved