1-(tert-butyldimethylsilyl)-4-oxoazetidine-2(R)-carboxylic acid | 188304-72-5

• 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: 1-(tert-butyldimethylsilyl)-4-oxoazetidine-2(R)-carboxylic acid
• 英文别名: (4S)-1-t-butyldimethylsilylazetidin-2-one-4-carboxylic acid；(S)-1-t-butyldimethylsilyl-2-azetidinone-4-carboxylic acid；(S)-1-t-butyldimethylsilyl-4-oxo-2-azetidinecarboxylic acid；1-tert-butyldimethylsilyl-4S-carboxyazetidin-2-one；N-(tert-butyldimethylsilyl)-4-oxo-azetidin-2-carboxylic acid；1-(Tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylic acid；1-[tert-butyl(dimethyl)silyl]-4-oxoazetidine-2-carboxylic acid
• CAS: 188304-72-5
• 化学式: C₁₀H₁₉NO₃Si
• mdl: MFCD11100946
• 分子量: 229.351
• InChiKey: LIEWITJXZYCDLE-UHFFFAOYSA-N

物化性质

• 沸点：
  309.3±35.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.27
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(tert-butyldimethylsilyl)-4-oxoazetidine-2(R)-carboxylic acid 在 四溴化碳 、 TEA 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 4-(2-Bromo-ethyl)-1-(tert-butyl-dimethyl-silanyl)-azetidin-2-one
  参考文献：
  名称：

  β-氨基丙烯酸酯的自由基环化：双环吡咯烷衍生物的合成

  摘要：

  衍生自4-（2-溴乙基）氮杂环丁烷-2-酮的β-氨基丙烯酸酯的自由基环化导致立体选择性地形成双环β-内酰胺产物，其可用作顺式-2,5-二取代的吡咯烷的前体。

  DOI：

  10.1016/s0040-4039(00)00970-9
• 作为产物：
  描述：

  4-benzyloxycarbonyl-1-t-butyldimethylsilyl-2-azetidinone 在 palladium on activated charcoal 氢气 作用下， 生成 1-(tert-butyldimethylsilyl)-4-oxoazetidine-2(R)-carboxylic acid
  参考文献：
  名称：

  新型与β-内酰胺环稠合的新型环状烯二炔内酯的合理设计，合成和反应性

  摘要：

  已经立体选择性地制备了与N-保护的和N-未保护的β-内酰胺反式融合的一系列10元环烯二炔。发现这些化合物对伯格曼环芳化反应是稳定的，另一方面，当氮杂环丁酮环打开时，该反应容易发生。

  DOI：

  10.1016/s0040-4020(97)00036-7

文献信息

• Cyclic dipeptides and azetidinone compounds and their use in treating CNS injury and neurodegenerative disorders
  申请人：Georgetown University

  公开号：US07202279B1

  公开（公告）日：2007-04-10

  The present invention provides 4-substituted-2-azetidinone compounds, bicyclic 2-5-diketopiperazine compounds, and pharmaceutical compositions thereof that are potent, safe and effective neuroprotective agents. Due to their strong central nervous system (CNS) activity, the compounds can be used to enhance memory and to treat a variety of neurological disorders. The compounds are particularly useful for treating neurological disorders caused by, or associated with, CNS trauma.

  本发明提供了4-取代-2-氮杂环己酮化合物、双环2-5-二酮哌嗪化合物及其药物组合物，它们是有效、安全且有效的神经保护剂。由于它们具有强大的中枢神经系统（CNS）活性，这些化合物可用于增强记忆力并治疗各种神经系统疾病。这些化合物特别适用于治疗由中枢神经系统创伤引起或与之相关的神经系统疾病。
• Beta lactam compounds and their use as inhibitors of tryptase
  申请人：Bristol-Myers Squibb Co.

  公开号：US06335324B1

  公开（公告）日：2002-01-01

  Compounds of the formulas: are disclosed. These compounds inhibit tryptase as well as other enzyme systems or are selective tryptase inhibitors and are useful as antiinflammatory agents particularly in the treatment of chronic asthma.

  这些化合物的结构式已被披露。这些化合物抑制色胺酸蛋白酶以及其他酶系统，或者是选择性色胺酸蛋白酶抑制剂，并且在特别是治疗慢性哮喘方面作为抗炎药物是有用的。
• Azetidinone derivatives for the treatment of HCMV infections
  申请人：Boehringer Ingelheim (Canada) Ltd.

  公开号：US06242439B1

  公开（公告）日：2001-06-05

  A compound of formula I wherein R1 is hydrogen, methyl, ethyl, methoxy or methylthio; R2 and R3 each independently is hydrogen or lower alkyl; R4 is hydrogen, lower alkyl, methoxy, ethoxy or benzyloxy; R5 is lower alkyl, lower cycloalkyl, (CH2)mC(O)OR6 wherein m is the integer 1 or 2 and R6 is lower alkyl, phenyl optionally substituted; optionally Het or Het(lower alkyl); or R4 and R5 together with the nitrogen atom to which they are attached form a nitrogen containing ring optionally substituted with C(O)O-benzyl or with phenyl optionally substituted with C(O)OR7 wherein R7 is lower alkyl or (lower alkyl)phenyl; and Z is lower alkyl or optionally substituted phenyl or Het; with the proviso that when Z is (CH2)p-(Het), then R2 and R3 each is hydrogen; or a therapeutically acceptable acid addition salt thereof which compound is useful in the treatment of HCMV infections.

  式I的化合物中，其中R1为氢、甲基、乙基、甲氧基或甲硫基；R2和R3各自独立地为氢或较低的烷基；R4为氢、较低的烷基、甲氧基、乙氧基或苄氧基；R5为较低的烷基、较低的环烷基、(CH2)mC(O)OR6，其中m是整数1或2，R6为较低的烷基、苯基可选择地取代；可选择地为Het或Het(较低的烷基)；或者R4和R5与它们连接的氮原子一起形成一个含氮环，该环可选择地取代为C(O)O-苄基或苯基，该苯基可选择地取代为C(O)OR7，其中R7为较低的烷基或(较低的烷基)苯基；Z为较低的烷基或可选择地取代的苯基或Het；但是当Z为(CH2)p-(Het)时，那么R2和R3各自为氢；或其治疗上可接受的酸盐，该化合物在HCMV感染的治疗中有用。
• Substituted azetidinones as anti-inflammatory and antidegenerative agents
  申请人：Merck & Co., Inc.

  公开号：US05229381A1

  公开（公告）日：1993-07-20

  New substituted azetidinones of the general formula (A') which have been found to be potent elastase inhibitors and thereby useful anti-inflammatory and antidegenerative agents are described. ##STR1##

  已发现具有强大弹性蛋白酶抑制剂作用的通用公式（A'）的新替代氮杂环丙酮类化合物，并因此被用作有用的抗炎和抗退行性药物。
• Synthesis and evaluation of N1/C4-substituted β-lactams as PPE and HLE inhibitors
  作者：Stéphane Gérard、Moreno Galleni、Georges Dive、Jacqueline Marchand-Brynaert

  DOI：10.1016/j.bmc.2003.10.009

  日期：2004.1

  4-(Alkylamino)carbonyl-1-(alkoxy)carbonyl-2-azetidinones (9-11) have been prepared in five steps from 4-(benzyloxy)carbonyl-1-(t-butyidimethyl)silyl-2-azetidinone (1). The P-lactam reactivity of 9 has been established by H-1 NMR experiment. Compound 11 was a good reversible inhibitor of PPE and HLE. Based on theoretical design, series of 2-azetidinones (12-17) and 4(alkoxy)carbonyl-2-azetidinones (18-21) bearing various carbonyl (ester, thiolester, amide) and thiocarbonyl (thioamide) functionalities at position N1 were similarly prepared. In the absence of C4-substituent, the compounds were inactive against elastases. On the other hand, 4-(benzyloxy)carbonyl-1-(ethylthioxy)carbonyl-2-azetidinone (19) and 4-(benzyloxy)carbonyl-1-(benzylamino)-thiocarbonyl-2-azetidinone (21) were both good reversible inhibitors, but acting most probably via different mechanisms (enzymic processing of the exocyclic ester function or beta-lactam ring opening). (C) 2003 Elsevier Ltd. All rights reserved.