(S)-(-)-1-benzylazetidine-2-carboxamide | 205443-26-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-(-)-1-benzylazetidine-2-carboxamide
• 英文别名: (2S)-1-benzylazetidine-2-carboxamide
• CAS: 205443-26-1
• 化学式: C₁₁H₁₄N₂O
• 分子量: 190.245
• InChiKey: NYSSYUHBYRIDQA-JTQLQIEISA-N

物化性质

• 熔点：
  93.0-94.0 °C
• 沸点：
  363.3±31.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 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：
  46.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(-)-1-benzylazetidine-2-carboxamide 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 11.0h， 以92%的产率得到氮杂环丁烷-2-甲酰胺
  参考文献：
  名称：

  7-（2-氨基甲基-1-氮杂环丁烷基）-4-氧代喹啉-3-羧酸作为有效的抗菌剂：设计，合成和抗菌活性。

  摘要：

  2-氨基甲基-1-氮杂环丁烷基，-1-吡咯烷基和-1-哌啶基被设计为新型C-7取代基，用于潜在的抗菌喹诺酮类药物。在三个取代基中，发现2-氨基甲基-1-氮杂环丁烷基（化合物12a）最有利于增强6,8-二氟喹啉分子12的活性。因此，2-氨基甲基-1-氮杂环丁烷基为引入各种喹啉（给24-26a和28a）和萘啶（给31a和32a）中。通过1-苄基氮杂环丁烷-2-羧酰胺的光学拆分（19）及其R-异构体的手性合成，还制备了2-氨基甲基-1-氮杂环丁烷基喹啉12a和24-26a的两个对映体。所有化合物中活性最高的是5-氨基-6,8-二氟喹啉（R）-26a。

  DOI：

  10.1248/cpb.46.787
• 作为产物：
  描述：

  N-苄基-2-氮杂环丁酸甲酯 在 immobilized lipase from Candida Antarctica 、 氨 作用下， 生成 (S)-(-)-1-benzylazetidine-2-carboxamide
  参考文献：
  名称：

  Enzymatic resolution of methyl N-alkyl-azetidine-2-carboxylates by Candida antarctica lipase-mediated ammoniolysis

  摘要：

  A facile method for the synthesis of optically active azetidine-2-carboxylic acid derivatives is presented. Racemic N-alkylated azetidine esters are resolved by lipase from Candida antarctica in an ammoniolysis reaction, and both the S-amide and the R-ester are obtained with excellent stereoselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00632-0

文献信息

• Highly Efficient and Enantioselective Biotransformations of Racemic Azetidine-2-carbonitriles and Their Synthetic Applications
  作者：Dong-Hui Leng、De-Xiang Wang、Jie Pan、Zhi-Tang Huang、Mei-Xiang Wang

  DOI：10.1021/jo9011656

  日期：2009.8.21

  Catalyzed by the Rhodococcus erythropolis AJ270 whole cell catalyst in neutral aqueous buffer at 30 degrees C, a number of racemic 1-benzylazetidine-2-carbonitriles, trans-1-benzyl-4-methylazetidine-2-carbonitrile. and 1-benzyl-2-methylazetidine-2-carbonitrile and their amide substrates underwent efficient and enantioselective biotransformations to afford the corresponding azetidine-2-carboxylic acids and their amide derivatives in excellent yields with cc up to >99.5%. The overall excellent, act enantioselectivity of the biocatalytic reactions stemmed from a combined effect of a very active but virtually nonenantioselective nitrite hydratase and a high R-enantioselective amidase involved in microbial whole cells. The synthetic applications have been demonstrated by the nucleophilic ring-opening reactions of azetidiniums of the resulting chiral azetidine-2-carbox amide derivatives for the preparation of alpha,gamma-diamino, alpha-phenoxy-gamma-amino, and alpha-cyano-gamma-amino carboxamides. The intramolecular Cul-catalyzed cross-coupling reaction for the synthesis of azetidine-fused 1,4-benzodiazepin-2-one derivative was also presented.
• Phyridonecarboxylic Acids as Antibacterial Agents. Part XX. 7-(2-Aminomethyl-1-azetidinyl)-4-oxoquinoline-3-carboxylic Acids as Potent Antibacterial Agents: Design, Synthesis, and Antibacterial Activity.
  作者：Masahiro FUJITA、Katsumi CHIBA、Yukio TOMINAGA、Katsuhiko HINO

  DOI：10.1248/cpb.46.787

  日期：——

  (giving 31a and 32a). Through optical resolution of 1-benzylazetidine-2-carboxamide (19) and chiral synthesis of its R-isomer, both enantiomers of 2-aminomethyl-1-azetidinyl quinolines 12a and 24-26a were also prepared. The most active of all the compounds was 5-amino-6,8-difluoroquinoline (R)-26a. The activity of (R)-26a was more potent than those of the corresponding 1-piperazinyl derivative (3) and sparfloxacin

  2-氨基甲基-1-氮杂环丁烷基，-1-吡咯烷基和-1-哌啶基被设计为新型C-7取代基，用于潜在的抗菌喹诺酮类药物。在三个取代基中，发现2-氨基甲基-1-氮杂环丁烷基（化合物12a）最有利于增强6,8-二氟喹啉分子12的活性。因此，2-氨基甲基-1-氮杂环丁烷基为引入各种喹啉（给24-26a和28a）和萘啶（给31a和32a）中。通过1-苄基氮杂环丁烷-2-羧酰胺的光学拆分（19）及其R-异构体的手性合成，还制备了2-氨基甲基-1-氮杂环丁烷基喹啉12a和24-26a的两个对映体。所有化合物中活性最高的是5-氨基-6,8-二氟喹啉（R）-26a。
• Enzymatic resolution of methyl N-alkyl-azetidine-2-carboxylates by Candida antarctica lipase-mediated ammoniolysis
  作者：Wim A.J Starmans、Roy G Doppen、Lambertus Thijs、Binne Zwanenburg

  DOI：10.1016/s0957-4166(97)00632-0

  日期：1998.2

  A facile method for the synthesis of optically active azetidine-2-carboxylic acid derivatives is presented. Racemic N-alkylated azetidine esters are resolved by lipase from Candida antarctica in an ammoniolysis reaction, and both the S-amide and the R-ester are obtained with excellent stereoselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.