methyl 2-oxo-1-carba-1-dethiapenam-3-carboxylate | 138126-40-6

• 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: methyl 2-oxo-1-carba-1-dethiapenam-3-carboxylate
• 英文别名: Methyl 3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 138126-40-6
• 化学式: C₈H₉NO₄
• 分子量: 183.164
• InChiKey: SWBUCYQWIBELOM-UHFFFAOYSA-N

物化性质

• 沸点：
  357.6±42.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene 在 dirhodium tetraacetate 三氟甲磺酸三甲基硅酯 作用下， 以 苯 为溶剂， 生成 methyl 2-oxo-1-carba-1-dethiapenam-3-carboxylate
  参考文献：
  名称：

  Direct conversion of N-alkoxy .beta.-lactams to carbapenams: application to the synthesis of the bicyclic PS-5 keto ester

  摘要：

  The synthesis and direct conversion of N-alkoxy beta-lactams to the carbapenam ring system is described. This novel cyclization apparently proceeds by initial carbene-mediated ylide formation with concomitant rearrangement. The title reaction is applied to the construction of the methyl ester of the bicyclic beta-lactam precursor of PS-5.

  DOI：

  10.1021/jo00008a022

文献信息

• Synthesis of the carbapenam ring system via carbene mediated rearrangement of an n-benzyloxy-β-lactam
  作者：Matthew A. Williams、Marvin J. Miller

  DOI：10.1016/s0040-4039(00)98791-4

  日期：——

  The α-diazoester1 in the presence of catalytic Rh2(OAc)4 was converted to the carbapenam2. The synthesis of1 and a proposed mechanism are described.

  在催化性Rh 2（OAc）4存在下，将α-重氮酸酯1转化为碳青霉烯2。描述了1的合成以及提出的机制。
• 6-Aminoalkyl carbapenems
  申请人：Bristol-Myers Squibb Company

  公开号：EP0372582A2

  公开（公告）日：1990-06-13

  Carbapenem compounds of formulae wherein R₁ is a lower alkyl, R₂ is hydrogen or a substituent other than amino are useful for the treatment of infections.

  式中的碳青霉烯类化合物 其中 R₁ 是低级烷基，R₂ 是氢或除氨基以外的取代基。
• Direct conversion of N-alkoxy .beta.-lactams to carbapenams: application to the synthesis of the bicyclic PS-5 keto ester
  作者：Matthew A. Williams、Chi Nung Hsiao、Marvin J. Miller

  DOI：10.1021/jo00008a022

  日期：1991.4

  The synthesis and direct conversion of N-alkoxy beta-lactams to the carbapenam ring system is described. This novel cyclization apparently proceeds by initial carbene-mediated ylide formation with concomitant rearrangement. The title reaction is applied to the construction of the methyl ester of the bicyclic beta-lactam precursor of PS-5.