(Pivaloyloxy)methyl 6α-chloropenicillanic acid | 118975-99-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Pivaloyloxy)methyl 6α-chloropenicillanic acid
• 英文别名: (pivaloyloxy)methyl 6α-chloro-penicillanate；(pivaloyloxy)methyl 6α-chloropenicillanate；2,2-dimethylpropanoyloxymethyl (2S,5R,6S)-6-chloro-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 118975-99-8
• 化学式: C₁₄H₂₀ClNO₅S
• 分子量: 349.836
• InChiKey: JWXVCUJGBWTKHJ-OYNCUSHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  98.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Pivaloyloxy)methyl 6α-chloropenicillanic acid 在 三丁基氧化锡 作用下， 以 乙醚 为溶剂， 生成 6-chloropenicillanic acid
  参考文献：
  名称：

  Scope and Mechanism of Deprotection of Carboxylic Esters by Bis(tributyltin) Oxide

  摘要：

  Methyl and ethyl esters of aliphatic and aromatic carboxylic acids as well as benzyl carboxylates, thiol esters and double esters such as (pivaloyloxy)methyl carboxylates have been successfully cleaved with bis(tributyltin) oxide to give the free carboxylic acids in good yields. The reaction is carried out in aprotic solvents under essentially neutral conditions and thus this method can serve as an ideal procedure for the cleavages of esters with other functional groups and/or protecting groups acid and/or base sensitive. We demonstrated that the reaction displays a high level of chemoselectivity between methyl and ethyl esters versus tert-butyl esters and gamma-lactones. Bis(tributyltin) oxide is also a highly efficient reagent for the cleavage of acetates of primary and secondary alcohols and phenols. The limitations we found in the use of this reagent include the lack. of cleavage of esters sterically hindered around the carboxyl carbon and the carbinol group (i.e., esters of tertiary alcohols) and in carboxylic esters that contain a fluoroalkyl substituent. A resonable mechanistic explanation is discussed to account for the reaction pathway of the acyloxygen cleavage of(-)-(1R)-menthyl acetate.

  DOI：

  10.1021/jo00103a016
• 作为产物：
  描述：

  pivaloyloxy methyl 6-β-iodo, 6α-chloro penicillinate 、 三正丁基氢锡 生成 (Pivaloyloxy)methyl 6α-chloropenicillanic acid
  参考文献：
  名称：

  BELINZONI, DIEGO U.;MATA, ERNESTO G.;MASCARETTI, ORESTE A., J. CHEM. RES. SYNOP.,(1988) N 6, C. 178

  摘要：

  DOI：

文献信息

• Chemo- and stereoselective reduction of (pivaloyloxy)methyl 6,6-dihalopenicillanates by trineophyltin hydride: Selective synthesis of 6β-halopenicillanates
  作者：Ernesto G. Mata、Oreste A. Mascaretti、Adriana E. Zuñiga、Alicia B. Chopa、Julio C. Podestá

  DOI：10.1016/s0040-4039(00)99280-3

  日期：1989.1

  A new Triorganotin hydride, Trineophyltin hydride was prepared and its chemo- and stereoselectivity towards reduction of Pom 6,6-homo- and hetero- dihalopenicillanates was examined. The trineophyltin hydride reveals higher stereoselectivity compared to that by tributyltin hydride at 25°C.

  制备了一种新的三有机锡氢化物，三氢叶绿素氢化物，并研究了其对还原Pom 6,6-同型和异二卤代黄花酸酯的化学和立体选择性。与三丁基锡氢化物在25°C时相比，氢化三叶新素具有更高的立体选择性。
• Belinzoni, Diego U.; Setti, Eduardo L.; Mascaretti, Oreste A., Journal of Chemical Research, Miniprint, 1988, # 6, p. 1501 - 1536
  作者：Belinzoni, Diego U.、Setti, Eduardo L.、Mascaretti, Oreste A.

  DOI：——

  日期：——
• Belinzoni, Diego U.; Mata, Ernesto G.; Mascaretti, Oreste A., Journal of Chemical Research, Miniprint, 1988, # 6, p. 1537 - 1548
  作者：Belinzoni, Diego U.、Mata, Ernesto G.、Mascaretti, Oreste A.

  DOI：——

  日期：——
• US4446144A
  申请人：——

  公开号：US4446144A

  公开（公告）日：1984-05-01
• US4511512A
  申请人：——

  公开号：US4511512A

  公开（公告）日：1985-04-16