(3R)-3-benzyl-1-[bis(trimethylsilyl)methyl]-3-(N,2-dimethyl-1,4-dihydronicotinamido)azetidin-2-one | 1224570-15-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3R)-3-benzyl-1-[bis(trimethylsilyl)methyl]-3-(N,2-dimethyl-1,4-dihydronicotinamido)azetidin-2-one
• 英文别名: N-[(3R)-3-benzyl-1-[bis(trimethylsilyl)methyl]-2-oxoazetidin-3-yl]-1,2-dimethyl-4H-pyridine-3-carboxamide
• CAS: 1224570-15-3
• 化学式: C₂₅H₃₉N₃O₂Si₂
• 分子量: 469.775
• InChiKey: ANIMRUAOUCVIAB-RUZDIDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-[(3R)-3-benzyl-1-[bis(trimethylsilyl)methyl]-2-oxoazetidin-3-yl]-1-methylpyridinium-3-carboxamide iodide 在 sodium dithionite 、 水 、 碳酸氢钠 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 (3R)-3-benzyl-1-[bis(trimethylsilyl)methyl]-3-(N,2-dimethyl-1,4-dihydronicotinamido)azetidin-2-one
  参考文献：
  名称：

  Stereomodulating effect of remote groups on the NADH-mimetic reduction of alkyl aroylformates with 1,4-dihydronicotinamide-β-lactam amides

  摘要：

  Conformationally restricted NADH peptidomimetics 4a-e, characterized by the presence of a (1,4-dihydronicotinamide)-(beta-lactam) moiety, have been synthesized and used to study the Mg2+ cation-promoted asymmetric reduction of alkyl aroylformates in acetonitrile. Increasing the bulkiness of peripheral substituents at the nitrogen atom of the beta-lactam ring, at the 1,4-dihydronicotinamide moiety, or at the aroylformate ester group, was found to cause weak but clearly detectable variations of the enantiomeric excess of the reaction. A rational for these observations was consistent with a chelated NADH/Mg2+/ArCOCO2R3 ternary complex model, according to DFT calculations computed at a B3LYP/631G(sic) theory level. (C) 2010 Elsevier Ltd. All tights reserved.

  DOI：

  10.1016/j.tet.2010.02.085

文献信息

• Stereomodulating effect of remote groups on the NADH-mimetic reduction of alkyl aroylformates with 1,4-dihydronicotinamide-β-lactam amides
  作者：Jesus M. Aizpurua、Claudio Palomo、Raluca M. Fratila、Pablo Ferrón、José I. Miranda

  DOI：10.1016/j.tet.2010.02.085

  日期：2010.4

  Conformationally restricted NADH peptidomimetics 4a-e, characterized by the presence of a (1,4-dihydronicotinamide)-(beta-lactam) moiety, have been synthesized and used to study the Mg2+ cation-promoted asymmetric reduction of alkyl aroylformates in acetonitrile. Increasing the bulkiness of peripheral substituents at the nitrogen atom of the beta-lactam ring, at the 1,4-dihydronicotinamide moiety, or at the aroylformate ester group, was found to cause weak but clearly detectable variations of the enantiomeric excess of the reaction. A rational for these observations was consistent with a chelated NADH/Mg2+/ArCOCO2R3 ternary complex model, according to DFT calculations computed at a B3LYP/631G(sic) theory level. (C) 2010 Elsevier Ltd. All tights reserved.