4-<2-hydroxy-1-methylethyl>-azetidin-2-one | 75486-38-3

• 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: 4-<2-hydroxy-1-methylethyl>-azetidin-2-one
• 英文别名: 4-(2-hydroxy-1-methyl-ethyl)-2-azetidinone；4-(1-methyl-2-hydroxyethyl)-2-azetidinone；4-(1-Hydroxypropan-2-yl)azetidin-2-one
• CAS: 75486-38-3
• 化学式: C₆H₁₁NO₂
• mdl: MFCD19217917
• 分子量: 129.159
• InChiKey: BWMRFFJBRCEWGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-<2-hydroxy-1-methylethyl>-azetidin-2-one 生成 (5S)-2,2,5-trimethyl-3-oxa-1-azabicyclo[4.2.0]octan-8-one
  参考文献：
  名称：

  CHRISTENSEN, B. G.;SHIH, D. H.

  摘要：

  DOI：
• 作为产物：
  描述：

  4-(1-methyl-2-acetoxyethyl)-2-azetidinone 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 4-<2-hydroxy-1-methylethyl>-azetidin-2-one
  参考文献：
  名称：

  6- and 1-Substituted-1-carbadethiapen-2-em-3-carboxylic acid

  摘要：

  本发明涉及以下结构的6-和1-取代的1-卡巴德硫杂青霉烷-2-烯-3-羧酸：##STR1## 其中R.sup.1，R.sup.2和R.sup.3是独立选择自氢，烷基，芳基和芳烷基等组的。这些化合物以及它们的药学上可接受的盐，酯和酰胺衍生物可用作抗生素。还揭示了制备这些化合物的过程，包括这些化合物的药物组合物和在需要抗生素效果时给予这些化合物和组合物的治疗方法。

  公开号：

  US04206219A1

文献信息

• Synthetic carbapenem antibiotics II. Stereoisomers of 7-hydroxyethyl-2,2,5-trimethyl-3-oxa-1-azabicyclo[4.2.O]octan-8-one
  作者：David H. Shih、Judith A. Fayter、L.D. Cama、Burton G. Christensen、Jordan Hirshfield

  DOI：10.1016/s0040-4039(00)89153-4

  日期：1985.1

  The titled compounds are key synthetic intermediates in the structure-activity relationship studies of novel 1-methyl carbapenem antibiotics. Preparation and structural determination of these stereoisomers by x-ray crystallography and proton NMR spectroscopy are reported.

  标题化合物是新型1-甲基碳青霉烯抗生素的结构-活性关系研究中的关键合成中间体。报道了通过X射线晶体学和质子NMR光谱法制备和立体确定这些立体异构体。
• 1-, 6- And 2-substituted-1-carba-2-penem-3-carboxylic acids
  申请人：Merck & Co., Inc.

  公开号：US04260627A1

  公开（公告）日：1981-04-07

  Disclosed are 1-, 6- and 2-substituted-1-carba-2-penem-3-carboxylic acids of the following structure: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are, inter alia, independently selected from the group consisting of hydrogen, alkyl, aryl, and aralkyl. Such compounds as well as their pharmaceutically acceptable salt, ester and amide derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds, pharmaceutical compositions comprising such compounds and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.

  本发明涉及以下结构的1-，6-和2-取代的1-卡巴-2-青霉烷-3-羧酸：##STR1## 其中R.sup.1，R.sup.2，R.sup.3和R.sup.4是独立地选自氢，烷基，芳基和芳烷基等组中的化合物。此类化合物及其药学上可接受的盐，酯和酰胺衍生物可用作抗生素。还公开了制备这种化合物的方法，包括含有这种化合物的制药组合物以及在需要抗生素效果时给予这种化合物和组合物的治疗方法。
• 6- and 1-Substituted-1-carbadethiapen-2-em-3-carboxylic acid
  申请人：Merck & Co., Inc.

  公开号：US04206219A1

  公开（公告）日：1980-06-03

  Disclosed are 6- and 1-substituted-1-carbadethiapen-2-em-3-carboxylic acids of the following structure: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are, inter alia, independently selected from the group consisting of hydrogen, alkyl, aryl, and aralkyl. Such compounds as well as their pharmaceutically acceptable salt, ester and amide derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds, pharmaceutical compositions comprising such compounds and methods of treatment comprising administering such compounds and compositions when an antibiotics effect is indicated.

  本发明涉及以下结构的6-和1-取代的1-卡巴德硫杂青霉烷-2-烯-3-羧酸：##STR1## 其中R.sup.1，R.sup.2和R.sup.3是独立选择自氢，烷基，芳基和芳烷基等组的。这些化合物以及它们的药学上可接受的盐，酯和酰胺衍生物可用作抗生素。还揭示了制备这些化合物的过程，包括这些化合物的药物组合物和在需要抗生素效果时给予这些化合物和组合物的治疗方法。
• 1-, 6- and 2-substituted-1-carba-2-penem-3-carboxylic acids, process for preparing the same and pharmaceutical compositions containing the same
  申请人：Merck & Co., Inc.

  公开号：EP0010316A1

  公开（公告）日：1980-04-30

  Disclosed are 1-, 6- and 2-substituted-1-carba -2-penem-3-carboxylic acids of the following structure: wherein R1, R2, R3 and R4 are, inter alia, independently selected from the group consisting of hydrogen, alkyl, aryl, and aralkyl. Such compounds as well as their pharmaceutically acceptable salt, ester and amide derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds and pharmaceutical compositions comprising such compounds.

  本发明公开了具有以下结构的 1-、6-和 2-取代-1-咔巴-2-烯-3-羧酸： 其中 R1、R2、R3 和 R4 除其他外独立地选自氢、烷基、芳基和芳烷基组成的组。此类化合物及其药学上可接受的盐、酯和酰胺衍生物可用作抗生素。此外，还公开了制备此类化合物和包含此类化合物的药物组合物的工艺。
• 1-, and 1,1-disubstituted-6-substituted-2-carbamimidoyl-1-carbadethiapen-2-em-3-carboxylic acids, a process for preparing and an antibiotic composition containing the same
  申请人：Merck & Co., Inc.

  公开号：EP0071908A1

  公开（公告）日：1983-02-16

  Disclosed are 1-, and 1,1-disubstituted-6-substituted-2-carbamimidoyl-1-carbadethiapen-2-em-3-carboxylic acids having the structure: wherein R9 and R10 are, inter alia, hydrogen R9 and R10 are not both hydrogen) alkyl, cycloalkyl, aryl, and aralkyl; R9 and R10 may be joined; R6 and R7 are, inter alia, independently selected from the group consisting of hydrogen, alkyl, alkenyl, aryl, aralkyl; A is a direct, single bond connecting the indicated S and C atoms, or A is a cyclic or acylic connecting group selected, inter alia, from alkyl, cycloalkyl, aryl, heteroaryl, heteroalkyl; R1 and R2, which define the carbamimidoyl function, are, inter alia, independently selected from hydrogen, alkyl, aryl; additionally, said carbamimidoyl is characterized by cyclic structures achieved by the joinder of the two nitrogen atoms via their substituents and by their joinder to connecting group A; additionally, "carbami- midiums" are disclosed by quarternization of on of the nitrogen atoms of said carbamimidoyl. Such compounds as well as their pharmaceutically acceptable salt, ester and amide derivates are useful as antibiotics. Also disclosed are processes for the preparation of such compounds and pharmaceutical compositions comprising such compounds.

  公开了具有以下结构的1-和1,1-二取代-6-取代-2-氨基甲酰亚胺基-1-碳二硫杂庚烯-2-em-3-羧酸： 其中 R9 和 R10 除其他外，是氢 R9 和 R10 不都是氢）烷基、环烷基、芳基和芳烷基；R9 和 R10 可以连接；R6 和 R7 除其他外，独立地选自氢、烷基、烯基、芳基、芳烷基组成的组；A 是连接所指 S 原子和 C 原子的直接单键，或者 A 是除其他外选自烷基、环烷基、芳基、杂芳基、杂烷基的环状或酰基连接基团；定义氨基甲酰亚胺官能团的 R1 和 R2 除其他外，独立地选自氢、烷基、芳基；此外，所述氨基甲酰亚胺的特征是通过取代基连接两个氮原子以及连接基 A 实现环状结构；此外，通过对所述氨基甲酰亚胺的一个氮原子进行仲氨化，公开了 "氨基甲酰亚胺"。此类化合物及其药学上可接受的盐、酯和酰胺衍生物可用作抗生素。此外，还公开了制备此类化合物和含有此类化合物的药物组合物的工艺。