(S)-Hexanedioic acid 3-hydroxy-1-methyl-6-(1,1-dimethylethyl)ester | 157435-79-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (S)-Hexanedioic acid 3-hydroxy-1-methyl-6-(1,1-dimethylethyl)ester
• 英文别名: 6-O-tert-butyl 1-O-methyl (3S)-3-hydroxyhexanedioate
• CAS: 157435-79-5
• 化学式: C₁₁H₂₀O₅
• 分子量: 232.277
• InChiKey: ARGBVCNUHXZIGB-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-Hexanedioic acid 3-hydroxy-1-methyl-6-(1,1-dimethylethyl)ester 在 四氯化碳 、 氢氧化钾 、 对甲苯磺酰叠氮 、 叠氮基三甲基硅烷 、 sodium carbonate 、 氯化铵 、 caesium carbonate 、 苯甲醚 、 三乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 28.58h， 生成 (2R,3R)-2-Azetidinepropanoic acid 1-<2-(phenylmethoxy)-2-oxoethyl>-4-oxo-3-azide
  参考文献：
  名称：

  Catalytic, Asymmetric Synthesis of the Carbacephem Framework

  摘要：

  A catalytic, asymmetric synthesis of the carbacephem beta-lactam framework is reported. The initial asymmetric center was established by catalytic hydrogenation of beta-keto ester 12 with (S)-Ru-BINAP. The beta-lactam ring was prepared using the hydroxamate approach (14 --> 15). The nitrogen substituent at C7 was introduced by the nucleophile transfer reaction (15 --> 17), and the six-membered ring of the carbacephem was prepared by a directed Dieckmann condensation (24 --> 25).

  DOI：

  10.1021/jo00096a031
• 作为产物：
  描述：

  单叔丁基琥珀酸酯 在 S-Ru-BINAP 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 65.0 ℃ 、344.73 kPa 条件下， 反应 20.0h， 生成 (S)-Hexanedioic acid 3-hydroxy-1-methyl-6-(1,1-dimethylethyl)ester
  参考文献：
  名称：

  Catalytic, Asymmetric Synthesis of the Carbacephem Framework

  摘要：

  A catalytic, asymmetric synthesis of the carbacephem beta-lactam framework is reported. The initial asymmetric center was established by catalytic hydrogenation of beta-keto ester 12 with (S)-Ru-BINAP. The beta-lactam ring was prepared using the hydroxamate approach (14 --> 15). The nitrogen substituent at C7 was introduced by the nucleophile transfer reaction (15 --> 17), and the six-membered ring of the carbacephem was prepared by a directed Dieckmann condensation (24 --> 25).

  DOI：

  10.1021/jo00096a031

文献信息

• N-Sulfonyloxy-β-lactam Inhibitors for β-Lactamases
  作者：Alexey Bulychev、John R. Bellettini、Michael O'Brien、Peter J. Crocker、Jean-Pierre Samama、Marvin J. Miller、Shahriar Mobashery

  DOI：10.1016/s0040-4020(00)00427-0

  日期：2000.7

  Structure-function analysis with a series of N-sulfonyloxy beta-lactam molecules as inhibitors of beta-lactamases is reported. The best of these compounds acylate the active site of the class A TEM-1 beta-lactamase from Escherichia coli rapidly, and resist deacylation. Whereas acylation of the active site of the class C beta-lactamase from Enterobacter cloacae was not seen, these compounds function as competitive inhibitors of this enzyme. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Catalytic, Asymmetric Synthesis of the Carbacephem Framework
  作者：Peter R. Guzzo、Marvin J. Miller

  DOI：10.1021/jo00096a031

  日期：1994.8

  A catalytic, asymmetric synthesis of the carbacephem beta-lactam framework is reported. The initial asymmetric center was established by catalytic hydrogenation of beta-keto ester 12 with (S)-Ru-BINAP. The beta-lactam ring was prepared using the hydroxamate approach (14 --> 15). The nitrogen substituent at C7 was introduced by the nucleophile transfer reaction (15 --> 17), and the six-membered ring of the carbacephem was prepared by a directed Dieckmann condensation (24 --> 25).