(S)-3-mercapto-1-[ N-(4-nitrobenzyloxycarbonyl)acetimidoyl]pyrrolidine | 211501-45-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-3-mercapto-1-[ N-(4-nitrobenzyloxycarbonyl)acetimidoyl]pyrrolidine
• 英文别名: (S)-3-mercapto-1-[N-(p-nitrobenzyloxycarbonyl)acetimidoyl]pyrrolidine；(S)-[1-(3-Mercapto-1-pyrrolidinyl)ethylidene]carbamic acid (4-nitrophenyl)methyl ester；(4-nitrophenyl)methyl (NE)-N-[1-[(3S)-3-sulfanylpyrrolidin-1-yl]ethylidene]carbamate
• CAS: 211501-45-0
• 化学式: C₁₄H₁₇N₃O₄S
• 分子量: 323.373
• InChiKey: ZQWBMXVEMVZOQI-LERPTODRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  88.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-3-mercapto-1-[ N-(4-nitrobenzyloxycarbonyl)acetimidoyl]pyrrolidine 在 三乙胺 sodium chloride 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 以86.1%的产率得到(3S,4R)-3-[(R)-1-t-Butyldimethylsilyloxyethyl]-4-([(S)-1-[N-(p-nitrobenzyloxycarbonyl)acetimidoyl]-pyrrolidin-3-ylthio]carbonylmethyl)-2-azetidinone
  参考文献：
  名称：

  Azetidinone derivatives, a process for their preparation and their use

  摘要：

  式(I)的化合物：##STR1##（其中R.sup.1代表氢或羟基保护基，R.sup.2和R.sup.3代表氢、烷基或芳基；R.sup.4代表可选择取代的烷基、脂环杂环、芳基、芳香杂环、可选择取代的烯基或可选择取代的炔基；R.sup.5代表氢或羧基保护基；R.sup.6代表烷氧基、芳氧基、二烷基氨基或二芳基氨基，或两个R.sup.6一起代表o-苯二氧基，或三个一起代表CH.sup.3 C(--CH.sub.2 O--).sub.3）可以通过将相应的羰基化合物与式P(R.sup.6).sub.3的化合物反应来制备。化合物(I)可以环化以制备羧基青霉素衍生物，其中许多具有有价值的抗生素活性。

  公开号：

  US05856556A1

文献信息

• Azetidinone compounds useful in the preparation of carbapenem
  申请人：Sankyo Company, Limited

  公开号：US05541317A1

  公开（公告）日：1996-07-30

  Compounds of formula (I): ##STR1## wherein: R.sup.1 is hydrogen or a hydroxy-protecting group; R.sup.2 is alkyl, alkoxy, halogen, optionally substituted phenyl or optionally substituted phenoxy; R.sup.3 is optionally substituted pyridyl, optionally substituted quinolyl or phenyl group which has a substituent of formula --CYNR.sup.5 R.sup.6, where Y is oxygen or sulfur, and R.sup.5 and R.sup.6 are each alkyl, aryl or aralkyl, or R.sup.5 and R.sup.6 and the nitrogen to which they are attached together form a heterocyclic group; is R.sup.4 hydrogen or an amino-protecting group; and Z is sulfur or oxygen; are valuable intermediates in the preparation of carbapenem compounds and retain a desirable configuration during conversion to such carbapenem compounds. Penem and carbapenem compounds having a group of formula --SA' are prepared from a corresponding compound having a substituted thio, sulfinyl or sulfonyl group at this position by reaction with a compound A'SH (where A' is an organic group) in the presence of a salt of a metal of Group II or III of the Periodic Table.

  化合物的化学式（I）：##STR1##其中：R.sup.1是氢或羟基保护基；R.sup.2是烷基，烷氧基，卤素，可选择取代的苯基或可选择取代的苯氧基；R.sup.3是可选择取代的吡啶基，可选择取代的喹啉基或带有化学式--CYNR.sup.5 R.sup.6的苯基，其中Y为氧或硫，R.sup.5和R.sup.6分别为烷基，芳基或芳基烷基，或R.sup.5和R.sup.6以及它们连接的氮共同形成杂环基；R.sup.4为氢或氨基保护基；Z为硫或氧；在头孢内酯类化合物的制备中是有价值的中间体，并在转化为这类头孢内酯类化合物时保持理想的构型。具有化学式--SA'的头孢内酯和头孢内酯类化合物是通过将在该位置具有取代硫，亚硫酰基或磺酰基团的相应化合物与存在于周期表第II或III族金属盐的存在下与化合物A'SH（其中A'为有机基）反应制备的。
• Practical Synthesis of 1.BETA.-Methylcarbapenem Antibiotics: Side Chain Substitution Reaction of 2-Arylsulfinyl and 2-Arylsulfonyl Carbapenems.
  作者：Kozo ODA、Akira YOSHIDA

  DOI：10.1248/cpb.46.893

  日期：——

  The C-2 side-chain substitution reaction of a sulfoxide and a sulfone derived from a p-nitrobenzyl (1R, 5S, 6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-[2-(diethylcarbamoyl)phenylthio]-1-methylcarbapen-2-em-3-carboxylate with various mercaptans progressed smoothly in the presence of magnesium bromide. Bromomagnesium thiolate prepared from mercaptans proved to be especially effective for the substitution reaction and gave precursors of 1β-methylcarbapenem antibiotics in high yield.

  由对硝基苄基 (1R,5S,6S)-6-[(1R)-1-(叔丁基二甲基硅氧基)乙基]-2-[2-(二乙基氨基甲酰基)苯硫基]-1-甲基碳青霉烯-2-em-3-甲酸酯衍生的亚砜和砜与各种硫醇的 C-2 侧链取代反应在溴化镁存在下进展顺利。由硫醇制备的硫酸溴镁被证明对取代反应特别有效，并能以高产率得到 1β- 甲基碳青霉烯类抗生素的前体。
• Azetidinone derivatives, a process for their preparation and their use as intermediates in the preparation of carbapenem antibiotics
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0102239A1

  公开（公告）日：1984-03-07

  Compounds of formula (I): (wherein R' represents hydrogen or a hydroxy-protecting group, R2 and R3 represent hydrogen, alkyl or aryl; R4 represents optionally substituted alkyl, alicyclic heterocyclic, aryl, aromatic heterocyclic, optionally substituted alkenyl or optionally substituted alkynyl; R6 represents hydrogen or a carboxy-protecting group; and R5 represents alkoxy, aryloxy, dialkylamino or diarylamino or two of R6 together represent o-phenylenedioxy or three together represent CH3C (-CH2O-)3) may be prepared by reacting the corresponding carbonyl compound with a compound of formula P(R6)3. Compounds (I) may be cyclised to prepare carbapenem derivatives, many of which have valuable antibiotic activity.

  式(I)化合物： (其中 R' 代表氢或羟基保护基团，R2 和 R3 代表氢、烷基或芳基；R4 代表任选取代的烷基、脂环杂环基、芳基、芳香杂环基、任选取代的烯基或任选取代的炔基；R6 代表氢或羧基保护基团；以及 R5 代表烷氧基、芳氧基、二烷基氨基或二芳基氨基或两个 R6 共同代表邻苯二氧基或三个 R6 共同代表 CH3C (-CH2O-)3)可通过相应的羰基化合物与式 P(R6)3 的化合物反应制备。化合物 (I) 可通过环化制备碳青霉烯衍生物，其中许多具有重要的抗生素活性。
• Carbapenem derivatives and compositions containing them
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0160391A1

  公开（公告）日：1985-11-06

  Compounds of formula (I): wherein: one or both of R' and R2 are selected from a variety of organic groups; R3 is an optionally substituted heterocycle; and R4 is hydrogen or optionally substituted alkyl or alkoxy. and salts and esters thereof have valuable antibiotic activity.

  式(I)化合物： 其中 R' 和 R2 中的一个或两个选自各种有机基团； R3 是任选取代的杂环；以及 R4 是氢或任选取代的烷基或烷氧基。 其盐类和酯类具有重要的抗生素活性。
• Process for preparing carbapenem and penem compounds and new compounds involved in that process
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0587436B1

  公开（公告）日：2000-05-10