Methyl (2R,3S)-3-phenyl-1H-aziridine-2-carboxylate | 129939-52-2

• 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: Methyl (2R,3S)-3-phenyl-1H-aziridine-2-carboxylate
• 英文别名: methyl (2R,3S)-(-)-3-phenylaziridine-2-carboxylate；methyl (2R,3S)-3-phenylaziridine-2-carboxylate
• CAS: 129939-52-2
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: FCVUIWBWIUKGDX-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  48.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl (2R,3S)-3-phenyl-1H-aziridine-2-carboxylate 生成 (2R,3S)-1-(Biphenyl-4-carbonyl)-3-phenyl-aziridine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  THIJS, LAMBERTUS;PORSKAMP, JOS J. M.;LOON, ADRIANN A. W. M. VAN;DERKS, MA+, TETRAHEDRON, 46,(1990) N, C. 2611-2622

  摘要：

  DOI：
• 作为产物：
  描述：

  3-苯基环氧乙烷甲酸乙酯 在 sodium azide 、 水 、 sodium ethanolate 作用下， 以 乙醚 、 水 、 乙腈 为溶剂， 反应 25.58h， 生成 Methyl (2R,3S)-3-phenyl-1H-aziridine-2-carboxylate
  参考文献：
  名称：

  Synthesis of all four homochiral stereoisomers of methyl 3-phenyl-1h-aziridine-2-car☐ylate

  摘要：

  DOI：

  10.1016/s0040-4020(01)82040-8

文献信息

• A convenient synthesis of aziridine-2-carboxylic esters
  作者：Johan Legters、Lambertus Thijs、Binne Zwanenburg

  DOI：10.1002/recl.19921110101

  日期：——

  Optically active oxirane-2-carboxylic esters, prepared from allylic alcohols employing the Sharpless epoxidation, were treated with sodium azide. The azido alcohols obtained were subsequently converted into aziridine-2-carboxylic esters by reaction with triphenylphosphine, in good yields and with high optical purity. Various racemic oxirane-2-carboxylic esters were subjected to the same sequence of

  用叠氮化钠处理由使用Sharpless环氧化的烯丙基醇制备的旋光环氧乙烷-2-羧酸酯。随后通过与三苯基膦反应以高收率和高光学纯度将获得的叠氮基醇转化为氮丙啶-2-羧酸酯。使各种外消旋环氧乙烷-2-羧酸酯进行相同的反应顺序。
• Convenient synthesis of optically active 2H-azirine-2-carboxylic esters by Swern oxidation of aziridine-2-carboxylic esters
  作者：Luca Gentilucci、Yvonne Grijzen、Lambertus Thijs、Binne Zwanenburg

  DOI：10.1016/0040-4039(95)00833-x

  日期：1995.6

  The synthesis of optically active 2H-azirine-2-carboxylic esters was achieved by Swern oxidation of the corresponding aziridine-carboxylic esters. For both trans and cis aziridine esters this oxidation gives a regioselective introduction of the double bond which is not in conjugation with the ester function. The methyl ester of ent-Azirinomycin was prepared in this manner.

  旋光的2 H-叠氮基-2-羧酸酯的合成是通过相应氮丙啶-羧酸酯的Swern氧化实现的。对于这两种反式和CIS氮丙啶酯该氧化给出一个区域选择性引入双键不与酯官能团缀合。以这种方式制备了对-阿奇霉素的甲酯。
• Asymmetric synthesis of syn hydroxyphenylalanine via aziridine ring expansion to an oxazoline
  作者：Giuliana Cardillo、Luca Gentilucci、Alessandra Tolomelli

  DOI：10.1016/s0040-4039(99)01734-7

  日期：1999.11

  The synthesis of (2R,3S)- and (2S,3R)-hydroxyphenylalanine is reported. The main steps are the 1,4-addition of O-benzylhydroxylamine to unsaturated imides and the ring expansion of trans-aziridines.

  报道了（2 R，3 S）-和（2 S，3 R）-羟基苯丙氨酸的合成。主要步骤是将O-苄基羟胺1，4-加成到不饱和酰亚胺上，以及反式-氮丙啶的扩环。
• Beta disubstituted metalloprotease inhibitors
  申请人：The Procter &Gamble Company

  公开号：US20040142975A1

  公开（公告）日：2004-07-22

  Disclosed are compounds which are inhibitors of metalloproteases and which are effective in treating conditions characterized by excess activity of these enzymes. In particular, the compounds have a structure according to the following Formula (I): 1 where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , G and Z have the meanings described in the specification. This invention also includes optical isomers, diastereomers and enantiomers of Formula I, and pharmaceutically-acceptable salts, biohydrolyzable amides, esters, and imides thereof. Also described are pharmaceutical compositions comprising these compounds, and methods of treating metalloprotease-related maladies using the compounds or the pharmaceutical compositions.

  本发明揭示了一类金属蛋白酶抑制剂，可用于治疗由这些酶过度活性引起的疾病。具体而言，该类化合物的结构如下式（I）所示：其中，R1、R2、R3、R4、R5、R6、G和Z的含义在说明书中有所描述。本发明还包括式（I）的光学异构体、对映异构体和对映体，以及其药学上可接受的盐、生物可水解的酰胺、酯和亚胺。此外，还描述了包含这些化合物的药物组合物，并使用这些化合物或药物组合物治疗金属蛋白酶相关疾病的方法。
• A convenient synthesis of optically active 1H-aziridine-2-carboxylic acids (esters)
  作者：J. Legters、L. Thijs、B. Zwanenburg

  DOI：10.1016/s0040-4039(01)80534-7

  日期：1989.1