4-nitrobenzyl 1-tert-butyldimethylsilyl-4,β-dioxo-2-azetidinebutyrate | 81946-77-2

• 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-nitrobenzyl 1-tert-butyldimethylsilyl-4,β-dioxo-2-azetidinebutyrate
• 英文别名: N-(t-butyldimethylsilyl)-4-[3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl]-azetidin-2-one；(4-nitrophenyl)methyl 4-[1-[tert-butyl(dimethyl)silyl]-4-oxoazetidin-2-yl]-3-oxobutanoate
• CAS: 81946-77-2
• 化学式: C₂₀H₂₈N₂O₆Si
• 分子量: 420.538
• InChiKey: ZAWBXXOJQIBFRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-nitrobenzyl 1-tert-butyldimethylsilyl-4,β-dioxo-2-azetidinebutyrate 生成 4-nitrobenzyl 4,β-dioxo-2-azetidinebutyrate
  参考文献：
  名称：

  CHRISTENSEN, BURTON G.;RATCLIFFE, RONALD W.

  摘要：

  DOI：
• 作为产物：
  描述：

  1-tert-butyldimethylsilyl-4-propargyl-2-azetidinone 以 四氢呋喃 为溶剂， 生成 4-nitrobenzyl 1-tert-butyldimethylsilyl-4,β-dioxo-2-azetidinebutyrate
  参考文献：
  名称：

  将丙二酸酯转化为β-酮酸酯的温和方法。在（±）-硫霉素的正式全合成中的应用

  摘要：

  据报道，通过硫醇加成将丙酸酯转化为β-酮酸酯的极其温和的方法，包括其成功地用于合成（±）-硫霉素的方法。

  DOI：

  10.1016/s0040-4039(00)88437-3

文献信息

• Process for preparing
  申请人：Merck & Co., Inc.

  公开号：US04820817A1

  公开（公告）日：1989-04-11

  Disclosed is a process for preparing 3-substituted-thio-6-(1'-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene -2-carboxylic acids (I) ##STR1## wherein X is a leaving group such as chloro, bromo, tosyl, mesyl or the like; and R.sup.8 is, inter alia, selected from the group consisting of hydrogen, alkyl, alkenyl, aryl and aralkyl. The compounds I as well as their pharmaceutically acceptable O- and carboxyl derivatives are useful as antibiotics.

  揭示了一种制备3-取代硫-6-(1'-羟乙基)-7-氧代-1-氮杂双环[3.2.0]庚-2-烯-2-羧酸(I)的过程##STR1##其中X是氯、溴、对甲苯磺酰基、甲磺酰基或类似物等离去基团；R.sup.8包括氢、烷基、烯基、芳基和芳基烷基等，化合物I及其药用可接受的O-和羧基衍生物可用作抗生素。
• 6- and
  申请人：Merck & Co. Inc.

  公开号：US05021566A1

  公开（公告）日：1991-06-04

  Disclosed are 6- and 6,6-disubstituted-3-substituted-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carbo xylic acids (I): ##STR1## wherein R.sup.1 and R.sup.2 are, inter alia, independently selected from the group consisting of hydrogen (both are not hydrogen at the same time), substituted and unsubstituted: alkyl, aryl and aralkyl; X is halo, oxygen (the 2-3 bond is saturated and the species I exists as carboxylate salt or ester), or --OR wherein R is, inter alia, acyl, alkyl, or aralkyl. Such compounds and 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.

  公开了6-和6,6-二取代-3-取代-1-氮杂双环[3.2.0]庚-2-烯-7-酮-2-羧酸（I）：其中R.sup.1和R.sup.2是，包括但不限于，独立选择自羟基（两者同时不是氢）的羟基，取代和未取代的：烷基，芳基和芳基烷基；X是卤素，氧（2-3键饱和且物种I存在为羧酸盐或酯），或--OR其中R是，包括但不限于，酰基，烷基或芳基烷基。这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。还公开了制备这类化合物的方法，包括这类化合物的药物组合物和在需要抗生素效果时给予这类化合物和组合物的治疗方法。
• 6-(1'-Hydroxyethyl)-3-substituted
  申请人：Merck & Co., Inc.

  公开号：US04424230A1

  公开（公告）日：1984-01-03

  Disclosed are 6-(1'-hydroxyethyl)-3-substituted amino-1-azabicyclo\x9b3.2.0!hept-2-en-7-one-2-carboxylic acids (I): \n' ##STR1## wherein R' and R" are independently selected from H, substituted and unsubstituted alkyl and aralkyl groups, or together form a substituted or unsubstituted cyclic group. Such compounds and their O- and carboxyl 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.

  揭示了6-(1'-羟乙基)-3-取代氨基-1-氮杂双环[3.2.0]庚-2-烯-7-酮-2-羧酸(I)：其中R'和R"分别选自H、取代和未取代的烷基和芳基烷基，或者一起形成取代或未取代的环状基团。这些化合物及其O-和羧酸衍生物可用作抗生素。还揭示了制备这类化合物的方法、包含这类化合物的药物组合物以及在需要抗生素效果时给予这类化合物和组合物的治疗方法。
• 6- And 6,6-disubstituted-3-substituted
  申请人：Merck & Co., Inc.

  公开号：US04530841A1

  公开（公告）日：1985-07-23

  Disclosed are 6- and 6,6-disubstituted-3-substituted amino-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylic acids (I): ##STR1## wherein R.sup.1 and R.sup.2 are, inter alia, independently selected from the group consisting of hydrogen, substituted and unsubstituted: alkyl, aryl, and aralkyl; and R' and R" are independently selected from the group consisting of: H, substituted and unsubstituted alkyl and aralkyl, or together form a substituted or unsubstituted cyclic group. Such compounds and 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 compounds and compositions when an antibiotic effect is indicated.

  揭示了6-和6,6-二取代-3-取代氨基-1-氮杂双环[3.2.0]庚-2-烯-7-酮-2-羧酸（I）：其中R.sup.1和R.sup.2等可独立地选择自氢、取代和未取代的烷基、芳基和芳基甲基等组成的群；R'和R"等可独立地选择自H、取代和未取代的烷基和芳基甲基，或者一起形成取代或未取代的环状基团。这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。还公开了制备这类化合物的方法、包含这类化合物的药物组合物以及在需要抗生素效果时给予化合物和组合物的治疗方法。
• 6-(1-Hydroxyethyl)-3-substituted-1-azabicyclo(3.2.0)-hept-2-en-7-one-2-ca
  申请人：Merck & Co., Inc.

  公开号：US04318912A1

  公开（公告）日：1982-03-09

  Disclosed are 6-(1'-hydroxyethyl)-3-substituted-1-azabicyclo[3.2.0]hept-2-en-7-one-2-car boxylic acids(I): ##STR1## wherein X is halo, oxygen (the 2-3 bond is saturated and the species I exists as the carboxylate salt or ester), or --OR wherein R is, inter alia, acyl, alkyl or aralkyl. Such compounds and their O- and carboxyl 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.

  揭示了6-(1'-羟乙基)-3-取代-1-氮杂双环[3.2.0]庚-2-烯-7-酮-2-羧酸(I)：其中X是卤素、氧（2-3键饱和，且该物种I存在为羧酸盐或酯），或--OR其中R是酰基、烷基或芳基烷基等。这些化合物及其O-和羧基衍生物可用作抗生素。还公开了制备这类化合物的方法、包含这类化合物的药物组合物以及在需要抗生素效果时给予这类化合物和组合物的治疗方法。