(S)-N-(p-toluenesulfonyl)azetidine-2-carboxylic acid | 39897-13-7

• 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: (S)-N-(p-toluenesulfonyl)azetidine-2-carboxylic acid
• 英文别名: 1-(4-toluenesulfonyl)azetidine-(2S)-carboxylic acid；(S)-1-tosylazetidine-2-carboxylic acid；L-N-tosylazetidine 2-carboxylic acid；(2S)-N-p-toluenesulfonylazetidine-2-carboxylic acid；(2S)-1-(4-methylphenyl)sulfonylazetidine-2-carboxylic acid
• CAS: 39897-13-7
• 化学式: C₁₁H₁₃NO₄S
• 分子量: 255.295
• InChiKey: PCZMDMOEFYSSGY-JTQLQIEISA-N

物化性质

• 沸点：
  458.3±55.0 °C(Predicted)
• 密度：
  1.435±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 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：
  83.1
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

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

反应信息

• 作为反应物：
  描述：

  (S)-N-(p-toluenesulfonyl)azetidine-2-carboxylic acid 在 N-甲基吗啉 、 1-羟基苯并三唑 、 戴斯-马丁氧化剂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-1-(Toluene-4-sulfonyl)-azetidine-2-carboxylic acid ((S)-1-formyl-2-phenyl-ethyl)-amide
  参考文献：
  名称：

  Peptidyl aldehyde inhibitors of calpain incorporating P2-proline mimetics

  摘要：

  Four new peptidyl aldehydes bearing proline mimetics at the P-2-Position were synthesized and studied as inhibitors of calpain 1, cathepsin B, and selected serine proteases. The ring size of the P-2-constraining residue influenced the inhibitory potency and selectivity of the compounds for calpain I compared to the other proteases. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00021-0
• 作为产物：
  描述：

  (S)-4-甲基-N-(2-氧代四氢呋喃-3-基)苯磺酰胺 在 lithium hydroxide 、 氯化亚砜 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 (S)-N-(p-toluenesulfonyl)azetidine-2-carboxylic acid
  参考文献：
  名称：

  N-甲苯磺酰基环状α-氨基酸的热Arndt-Eistert反应

  摘要：

  摘要 研究了 N-甲苯磺酰基环状 α-氨基酸的热 Arndt-Eistert 反应，以探索带有末端甲苯磺酰基氨基的 α,β-不饱和酯的制备。对于L-N-甲苯磺酰基-氮丙啶2-羧酸和L-N-甲苯磺酰基-氮杂环丁烷2-羧酸，可以立体定向地获得相应的(E)-α,β-不饱和酯。

  DOI：

  10.1080/00397910500213021

文献信息

• Novel chiral dirhodium catalysts derived from aziridine and azetidine carboxylic acid for intermolecular cyclopropanation reactions with methyl phenyldiazoacetate
  作者：Wim A.J. Starmans、Lambertus Thijs、Binne Zwanenburg

  DOI：10.1016/s0040-4020(97)10322-2

  日期：1998.1

  Three new chiral dirhodium(II) tetracarboxylate catalysts, based on azetidine- and aziridine-2-carboxylic acid, were prepared. Their selectivities in the cyclopropanation reaction of methyl phenyldiazoacetate and olefins were determined in solvents of decreasing polarity and compared with those obtained with proline derived catalysts.

  制备了三种新的基于氮杂环丁烷-和氮丙啶-2-羧酸的手性四羧酸二铑（II）手性催化剂。在极性递减的溶剂中测定了它们在苯基重氮乙酸甲酯和烯烃的环丙烷化反应中的选择性，并将其与脯氨酸衍生的催化剂的选择性进行了比较。
• Process for preparation of optically active n-substituted azetidine-2-carboxylic acids
  申请人：——

  公开号：US20030045730A1

  公开（公告）日：2003-03-06

  The object of the present invention is to produce an optically active N-substituted azetidine-2-carboxylic acid by an efficient, expedient and commercially profitable process. The present invention provides a production method of an optically active N-substituted azetidine-2-carboxylic acid which comprises cyclizing an optically active 4-substituted amino-2-halobutyric acid in the presence of a base.

  本发明的目的是通过一种高效、快捷且商业利润丰厚的方法生产光学活性的N-取代的氮杂环-2-羧酸。本发明提供了一种生产光学活性的N-取代的氮杂环-2-羧酸的方法，其包括在碱的存在下使光学活性的4-取代氨基-2-卤丙酸环化。
• Process for producing optically active N-substituted azetidine-2-carboxylic acid compound
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP0974670A2

  公开（公告）日：2000-01-26

  There is provided a process for producing an optically active N-substituted azetidine-2-carboxylic acid compound represented by the formula (2): by contacting a corresponding N-substituted azetidine-2-carboxylic acid ester of formula (2) with an enzyme derived from a microorganism selected from Arthrobacter SC-6-98-28 strain, Arthrobacter sp. ATCC21908 strain, Chromobacterium SC-YM-1 strain, and a mutant thereof. A process is also provided for preparing an optically active azetidine-2-carboxylic acid by eliminating the N-substituent of a N-substituted azetidine-2-carboxylic acid ester of formula (2).

  提供了一种生产具有光学活性的 N-取代氮杂环丁烷-2-羧酸化合物的工艺，该化合物由式（2）代表： 将相应的式(2)N-取代的氮杂环丁烷-2-羧酸酯与一种酶接触，该酶来源于一种微生物，该微生物选自节杆菌 SC-6-98-28 株、节杆菌 ATCC21908 株、色杆菌 SC-YM-1 株及其突变体。还提供了一种通过消除式（2）N-取代的氮杂环丁烷-2-羧酸酯的 N-取代基来制备光学活性氮杂环丁烷-2-羧酸的工艺。
• Enantiodivergent synthesis of N-protected azetidine-2-carboxylic acid
  作者：Tanmoy Biswas、Jyoti Prasad Mukherjee、Shital K. Chattopadhyay

  DOI：10.1016/j.tetasy.2012.08.016

  日期：2012.10

  A new route to both enantiomers of N-tosyl-azetidine-2- carboxylic acid has been developed from (R)-2-cyclohexylideneglyceraldehyde which proceeded with good overall yield and excellent enantiomeric purity. (C) 2012 Elsevier Ltd. All rights reserved.
• PROCESS FOR PREPARATION OF OPTICALLY ACTIVE N-SUBSTITUTED AZETIDINE-2-CARBOXYLIC ACIDS
  申请人：KANEKA CORPORATION

  公开号：EP1170287B1

  公开（公告）日：2003-12-03