(2S,3R,4S,5R)-diethyl-2-(10,10-dimethyl-3,3-dioxo-3λ(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decan-4-ylcarbonyl)-5-phenylpyrrolidine-3,4-dicarboxylate | 1192382-16-3

• 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: (2S,3R,4S,5R)-diethyl-2-(10,10-dimethyl-3,3-dioxo-3λ(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decan-4-ylcarbonyl)-5-phenylpyrrolidine-3,4-dicarboxylate
• CAS: 1192382-16-3
• 化学式: C₂₇H₃₆N₂O₇S
• 分子量: 532.658
• InChiKey: GXUYQGQTIOJKKB-PHEOHUQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  119.08
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  、 苯甲醛 、 马来酸二乙酯 在 silver(I) acetate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以50%的产率得到(2S,3R,4S,5R)-diethyl-2-(10,10-dimethyl-3,3-dioxo-3λ(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decan-4-ylcarbonyl)-5-phenylpyrrolidine-3,4-dicarboxylate
  参考文献：
  名称：

  (2S,3R,4S,5R)-Diethyl 2-(10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]decan-4-ylcarbonyl)-5-phenylpyrrolidine-3,4-dicarboxylate: a novel isomorphous-by-addition compound

  摘要：

  The title compound, C27H36N2O7S, (I), is isomorphous by addition with the dimethyl ester analogue [Garner, Dogan, Youngs, Kennedy, Protasiewicz & Zaniewski (2001). Tetrahedron, 57, 71-85], (II), by replacing two methyl ester H atoms with two methyl groups. With the exception of the conformation of one of the ester groups, the molecules are almost superimposable. Likewise, apart from a slightly larger c axis in (I), few differences in the cell packing of (I) and (II) are found, with both dominated by the same C-H center dot center dot center dot O hydrogen bonds. Full synthetic and spectroscopic details of (I) are given. The molecular synthesis is important as an example of chiral auxiliary-assisted 1,3-dipolar cycloaddition of an azomethine ylid.

  DOI：

  10.1107/s0108270108040584