methyl 2-<(2R)-2-(benzothiazol-2-yldisulphanyl)-4-oxoazetidin-1-yl>-3-methylbut-2-enoate | 69078-05-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: methyl 2-<(2R)-2-(benzothiazol-2-yldisulphanyl)-4-oxoazetidin-1-yl>-3-methylbut-2-enoate
• 英文别名: methyl 2-<-4-(2-benzothiazolyldithio)-2-azetidinon-1-yl>-3-methyl-2-butenoate；2-(2-benzothiazol-2-yldisulfanyl-4-oxo-azetidin-1-yl)-3-methyl-but-2-enoic acid methyl ester；2-[(4R)-4-(benzthiazol-2-yldithio)-2-oxoazetidin-1-yl]-3-methylcrotonic acid methyl ester；2-[(4R)-4-(benzthiazol-2-yl-dithio)-2-oxoazetidin-1yl]-3-methylcrotonic acid methyl ester；methyl 2-[(2R)-2-(1,3-benzothiazol-2-yldisulfanyl)-4-oxoazetidin-1-yl]-3-methylbut-2-enoate
• CAS: 69078-05-3
• 化学式: C₁₆H₁₆N₂O₃S₃
• 分子量: 380.513
• InChiKey: VSDKBALLNLDCQO-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-<(2R)-2-(benzothiazol-2-yldisulphanyl)-4-oxoazetidin-1-yl>-3-methylbut-2-enoate 生成 2-[(4R)-4-acetylthio-2-oxoazetidin-1-yl]-3-methylcrotonic acid methyl ester
  参考文献：
  名称：

  GOSTELI, J.;ERNEST, I.;WOODWARD, R. B.

  摘要：

  DOI：
• 作为产物：
  描述：

  6-氨基青霉烷酸 在 Pd/BaCO₃ 氢气 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 4.0h， 生成 methyl 2-<(2R)-2-(benzothiazol-2-yldisulphanyl)-4-oxoazetidin-1-yl>-3-methylbut-2-enoate
  参考文献：
  名称：

  The penems, a new class of .beta.-lactam antibiotics. 3. Synthesis of optically active 2-methyl-(5R)-penem-3-carboxylic acid

  摘要：

  DOI：

  10.1021/ja00515a025

文献信息

• Thia-aza compounds with a .beta.-lactam ring
  申请人：Ciba-Geigy Corporation

  公开号：US04331676A1

  公开（公告）日：1982-05-25

  2-Penem-3-carboxylic acid compounds of the formula ##STR1## in which R.sub.1 represents hydrogen, an organic radical bonded by a carbon atom to the ring carbon atom or an etherified mercapto group and R.sub.2 represents hydroxy or a radical R.sub.2.sup.A forming together with the carbonyl grouping --C(.dbd.O)-- a protected carboxyl group, 1-oxides thereof, as well as salts of such compounds having salt-forming groups, in racemic and optically active form, processes for their preparation, pharmaceutical compositions containing such compounds, and their use as antibiotics, and intermediates and their processes which are useful in the production of the compounds of the formula I.

  公式为##STR1##的2-青霉素-3-羧酸化合物，其中R.sub.1代表氢，由碳原子与环碳原子结合的有机基团或醚化巯基团，R.sub.2代表羟基或与羰基团--C(.dbd.O)--一起形成保护羧基的基团R.sub.2.sup.A，其1-氧化物，以及具有形成盐的盐基团的这种化合物的盐，以拉克米和光学活性形式存在，它们的制备方法，含有这种化合物的药物组合物，以及它们作为抗生素的用途，以及在生产公式I化合物中有用的中间体及其制备方法。
• Reactions of Disulfides Derived from Penicillin Sulfoxides with Tertiary Phosphines in Presence of Carboxylic Acids
  作者：Kapa Prasad、Helmut Hamberger、Peter Stüutz、Gerhard Schulz

  DOI：10.1002/hlca.19810640128

  日期：1981.2.4

  A novel method for the preparation of thioesters starting from Iso-Fujisawa disulfides is reported. The presence of an acylamino group cis to the disulfide function on the β-lactam nucleus seems to be an essential requirement for this reaction. In the absence of such a cis-acylamino group, desulfurization, is the preferred course.

  据报道，从二藤异藤泽开始制备硫酯的新方法。在β-内酰胺核上存在与二硫键功能顺式的酰氨基似乎是该反应的必要条件。在不存在这种顺式-酰基氨基的情况下，脱硫是优选的过程。
• Intermediates for thia-aza compounds with a .beta.-lactam ring
  申请人：Ciba-Geigy Corporation

  公开号：US04447360A1

  公开（公告）日：1984-05-08

  2-Penem-3-carboxylic acid compounds of the formula ##STR1## in which R.sub.1 represents hydrogen, an organic radical bonded by a carbon atom to the ring carbon atom or an etherified mercapto group and R.sub.2 represents hydroxy or a radical R.sub.2.sup.A forming together with the carbonyl grouping --C(.dbd.O)-- a protected carboxyl group, 1-oxides thereof, as well as salts of such compounds having salt-forming groups, in racemic and optically active form, processes for their preparation, pharmaceutical compositions containing such compounds, and their use as antibiotics, and intermediates and their processes which are useful in the production of the compounds of the formula I.

  公式为 ##STR1## 的2-Penem-3-羧酸化合物，其中R.sub.1代表氢、通过碳原子与环碳原子结合的有机基团或醚化的巯基团，R.sub.2代表羟基或与羰基团--C(.dbd.O)--形成保护羧基团的基团R.sub.2.sup.A，其1-氧化物，以及具有形成盐的基团的这种化合物的盐，包括外消旋和光学活性形式，其制备过程，含有这种化合物的制药组合物，以及它们作为抗生素的用途，以及在公式I化合物的生产中有用的中间体和它们的制备方法。
• Azetidinone-4-disulfides as intermediates for thia-aza compounds with a
  申请人：Ciba Geigy Corporation

  公开号：US04518533A1

  公开（公告）日：1985-05-21

  2-Penem-3-carboxylic acid compounds of the formula ##STR1## in which R.sub.1 represents hydrogen, an organic radical bonded by a carbon atom to the ring carbon atom or an etherified mercapto group and R.sub.2 represents hydroxy or a radical R.sub.2.sup.A forming together with the carbonyl grouping --C(.dbd.O)--a protected carboxyl group, 1-oxides thereof, as well as salts of such compounds having salt-forming groups, in racemic and optically active form, processes for their preparation, pharmaceutical compositions containing such compounds, and their use as antibiotics, and intermediates and their processes which are useful in the production of the compounds of the formula I.

  公式为##STR1##的2-Penem-3-羧酸化合物，其中R.sub.1代表氢，通过碳原子与环碳原子相结合的有机基团或醚化巯基团，R.sub.2代表羟基或与羰基团--C(.dbd.O)--形成保护羧基团的基团R.sub.2.sup.A，其1-氧化物，以及具有成盐基团的这样的化合物的盐，包括外消旋和光学活性形式，其制备过程，含有这样的化合物的制药组合物，以及它们作为抗生素的用途，以及用于制备公式I化合物的中间体及其制备过程。
• Process for preparing thia-aza compounds with a beta-lactam ring
  申请人：Ciba-Geigy Corporation

  公开号：US04500457A1

  公开（公告）日：1985-02-19

  2-Penem-3-carboxylic acid compounds of the formula ##STR1## in which R.sub.1 represents hydrogen, an organic radical bonded by a carbon atom to the ring carbon atom or an etherified mercapto group and R.sub.2 represents hydroxy or a radical R.sub.2.sup.A forming together with the carbonyl grouping --C(.dbd.O)-- a protected carboxyl group, 1-oxides thereof, as well as salts of such compounds having salt-forming groups, in racemic and optically active form, processes for their preparation, pharmaceutical compositions containing such compounds, and their use as antibiotics, and intermediates and their processes which are useful in the production of the compounds of the formula I.

  公式为##STR1##的2-Penem-3-羧酸化合物，其中R.sub.1代表氢，通过碳原子与环碳原子连接的有机基团或醚化巯基团，R.sub.2代表羟基或与羰基团--C(.dbd.O)--一起形成受保护羧基团的基团R.sub.2.sup.A，其1-氧化物，以及具有形成盐的基团的这种化合物的盐，包括外消旋和光学活性形式，它们的制备过程，含有这种化合物的制药组合物，以及它们作为抗生素的用途，以及在公式I的化合物的生产中有用的中间体和它们的制备过程。