(2R,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[(E)-2-(ethoxycarbonyl)vinyl]pyrrolidine | 442681-34-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2R,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[(E)-2-(ethoxycarbonyl)vinyl]pyrrolidine
• 英文别名: (2R,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[(E)-2-ethoxycarbonylvinyl]-pyrrolidine；tert-butyl (2R,4R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[(E)-3-ethoxy-3-oxoprop-1-enyl]pyrrolidine-1-carboxylate
• CAS: 442681-34-7
• 化学式: C₂₀H₃₇NO₅Si
• 分子量: 399.603
• InChiKey: QVOBTVSKXXGUCZ-HMUVLFPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[(E)-2-(ethoxycarbonyl)vinyl]pyrrolidine 在 镍 咪唑 、 盐酸 、 lithium aluminium tetrahydride 、 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 氢气 、 sodium hydride 、 magnesium 、 溶剂黄146 、 N,N-二异丙基乙胺 、 三苯基膦 、 sodium chloride 、 mercury dichloride 、 三甲基膦 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， -20.0~160.0 ℃ 、354.64 kPa 条件下， 反应 88.67h， 生成 (2R,4R)-4-acetoxy-2-[4-(N-allyloxycarbonylaminomethyl)cyclohexyl]-1-allyloxycarbonylpyrrolidine
  参考文献：
  名称：

  Structure–Activity Relationships of 1β-Methyl-2-(5-phenylpyrrolidin-3-ylthio)carbapenems

  摘要：

  Structure-activity relationship studies of 1beta-methyl-2-[(3S,5R)-5-(4-aminomethylphenyl)pyrrolidin-3-ylthio]carbapenems, especially those pertaining to the relationship between antibacterial activity and side-chain structure were conducted. These studies suggested that the trans-(3S,5R)-5-phenylpyrrolidin-3-ylthio side-chain and the aminomethyl group at the 4-position of the phenyl ring play a key role in enhancing the antibacterial activity against the MRSA and Pseudomonas aeruginosa strains. In particular, the basicity of a substituent at the 4-position of the phenyl ring were shown to greatly contribute to the antibacterial activity against MRSA and methicillin-resistant Staphlyloccocus epidermidis strains. In contrast, the amidine group was shown to lead to potent antibacterial activity against P. aeruginosa strains comparable to that of imipenem, however, a good correlation between the basicity of the 4-substituent and antipseudomonal activity was not observed. In conclusion, the 4-aminomethyl or methylaminomethyl group on the phenyl ring was the best substituent for antipseudomonal activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00430-8
• 作为产物：
  描述：

  磷酰基乙酸三乙酯 、 (2R,4R)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-formyl-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.17h， 以94.8%的产率得到(2R,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[(E)-2-(ethoxycarbonyl)vinyl]pyrrolidine
  参考文献：
  名称：

  Structure–Activity Relationships of 1β-Methyl-2-(5-phenylpyrrolidin-3-ylthio)carbapenems

  摘要：

  Structure-activity relationship studies of 1beta-methyl-2-[(3S,5R)-5-(4-aminomethylphenyl)pyrrolidin-3-ylthio]carbapenems, especially those pertaining to the relationship between antibacterial activity and side-chain structure were conducted. These studies suggested that the trans-(3S,5R)-5-phenylpyrrolidin-3-ylthio side-chain and the aminomethyl group at the 4-position of the phenyl ring play a key role in enhancing the antibacterial activity against the MRSA and Pseudomonas aeruginosa strains. In particular, the basicity of a substituent at the 4-position of the phenyl ring were shown to greatly contribute to the antibacterial activity against MRSA and methicillin-resistant Staphlyloccocus epidermidis strains. In contrast, the amidine group was shown to lead to potent antibacterial activity against P. aeruginosa strains comparable to that of imipenem, however, a good correlation between the basicity of the 4-substituent and antipseudomonal activity was not observed. In conclusion, the 4-aminomethyl or methylaminomethyl group on the phenyl ring was the best substituent for antipseudomonal activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00430-8

文献信息

• Alkylaminoalkylpyrrolidinylthiocarbapenem derivatives
  申请人：Banyu Pharmaceutical Co., Ltd.

  公开号：US05449672A1

  公开（公告）日：1995-09-12

  A compound of the formula: ##STR1## wherein R.sup.1 is a hydrogen atom or a methyl group, R.sup.2 is a hydrogen atom or a negative charge, X is a group of --N(R.sup.3)R.sup.4 (wherein R.sup.3 is a lower alkyl group, and R.sup.4 is a hydrogen atom or a lower alkyl group) or a group of --N.sup.+ (R.sup.5)(R.sup.6)R.sup.7 (wherein each of R.sup.5, R.sup.6 and R.sup.7 which may be the same or different, is a lower alkyl group), and n is an integer of from 2 to 4; or a pharmaceutically acceptable salt or ester thereof.

  化合物的式子为：##STR1## 其中R.sup.1为氢原子或甲基基团，R.sup.2为氢原子或负电荷，X为--N(R.sup.3)R.sup.4基团（其中R.sup.3为较低烷基基团，R.sup.4为氢原子或较低烷基基团）或--N.sup.+ (R.sup.5)(R.sup.6)R.sup.7基团（其中R.sup.5、R.sup.6和R.sup.7可以相同也可以不同，均为较低烷基基团），n为2到4之间的整数；或其药学上可接受的盐或酯。