N-benzoyl S-proline ethyl ester | 89311-11-5

• 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: N-benzoyl S-proline ethyl ester
• 英文别名: 1-Benzoyl-l-proline ethyl ester；ethyl (2S)-1-benzoylpyrrolidine-2-carboxylate
• CAS: 89311-11-5
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: TXUQAKVXQRMKML-LBPRGKRZSA-N

物化性质

• 沸点：
  375.6±35.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzoyl S-proline ethyl ester 在 劳森试剂 、 sodium hydroxide 、 rhodium(II) octanoate 、 三乙胺 、 甲烷磺酰基叠氮化物 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 丙酮 、 苯 为溶剂， 反应 67.0h， 生成 dimethyl 2,3-dihydro-5-phenyl-1H-pyrrolizine-6,7-dicarboxylate
  参考文献：
  名称：

  Rhodium(II) Catalyzed Cyclization of Diazo Thiocarbonyl Compounds for Heterocycloic Synthesis

  摘要：

  The mesoionic thioisomunchnone system was prepared from the rhodium(II) acetate catalyzed cyclization of a diazothioamide and was found to undergo smooth 1,3-dipolar cycloaddition with N-phenylmaleimide. In contrast to this system, the rhodium(II) reaction of an alpha-diazo-beta-oxo ester containing a thiocarbonyl group produced a cyclic thiocarbonyl ylide which extruded sulfur from a transient episulfide intermediate.

  DOI：

  10.3987/com-92-s29
• 作为产物：
  描述：

  L-脯氨酸 在 sodium hydroxide 、 sodium carbonate 、 对甲苯磺酸 作用下， 反应 9.5h， 生成 N-benzoyl S-proline ethyl ester
  参考文献：
  名称：

  Rhodium(II) Catalyzed Cyclization of Diazo Thiocarbonyl Compounds for Heterocycloic Synthesis

  摘要：

  The mesoionic thioisomunchnone system was prepared from the rhodium(II) acetate catalyzed cyclization of a diazothioamide and was found to undergo smooth 1,3-dipolar cycloaddition with N-phenylmaleimide. In contrast to this system, the rhodium(II) reaction of an alpha-diazo-beta-oxo ester containing a thiocarbonyl group produced a cyclic thiocarbonyl ylide which extruded sulfur from a transient episulfide intermediate.

  DOI：

  10.3987/com-92-s29

文献信息

• Studies on amino acids and peptides—IV
  作者：T.P. Andersen、A.-B.A.G. Ghattas、S.-O. Lawesson

  DOI：10.1016/s0040-4020(01)91595-9

  日期：1983.1

  Ethyl esters 2 of N-acyl derivatives of glycine, S-alanine, S-phenylalanine, and S-proline, were thionated by use of 2,4 - bis(4 - methoxyphenyl) - 1,3,2,4 - dithiadiphosphetane 2,4-disulfide (Lawesson's Reagent) 1. The N-thioacyl compounds 3 were reacted with hydrazine hydrate and in most cases a ring-closure reaction took place, giving 1,2,4-triazine derivatives 4. The structural proofs of 4 were

  甘氨酸，S-丙氨酸，S-苯丙氨酸和S-脯氨酸的N-酰基衍生物的乙酯2通过使用2,4-双（4-甲氧基苯基）-1,3,2,4-二硫代二膦烷2进行亚硫酰化，4-二硫键（Lawesson试剂）1。使N-硫酰基化合物3与水合肼反应，并且在大多数情况下发生闭环反应，得到1,2,4-三嗪衍生物4。通过1 H，13 C和15 N NMR光谱获得4的结构证明。
• General Pyrrolidine Synthesis via Iridium-Catalyzed Reductive Azomethine Ylide Generation from Tertiary Amides and Lactams
  作者：Ken Yamazaki、Pablo Gabriel、Graziano Di Carmine、Julia Pedroni、Mirxan Farizyan、Trevor A. Hamlin、Darren J. Dixon

  DOI：10.1021/acscatal.1c01589

  日期：2021.6.18

  accessible. Subsequent regio- and diastereoselective, inter- and intramolecular dipolar cycloaddition reactions with variously substituted electron-deficient alkenes enabled ready and efficient access to structurally complex pyrrolidine architectures. Density functional theory (DFT) calculations of the dipolar cycloaddition reactions uncovered an intimate balance between asynchronicity and interaction energies

  描述了稳定和不稳定偶氮甲碱叶立德的铱催化还原生成及其在通过 [3 + 2] 偶极环加成反应合成功能化吡咯烷中的应用。在温和的反应条件下，使用 1 mol% Vaska 配合物 [IrCl(CO)(PPh 3 ) 2，从具有适当位置的吸电子或三甲基甲硅烷基的酰胺和内酰胺前体进行反应] 和四甲基二硅氧烷 (TMDS) 作为末端还原剂，可以使用范围广泛的（未）稳定的偶氮甲碱叶立德。随后的区域选择性和非对映选择性、分子间和分子内偶极环加成反应与各种取代的缺电子烯烃能够快速有效地获得结构复杂的吡咯烷结构。偶极环加成反应的密度泛函理论 (DFT) 计算揭示了过渡结构的异步性和相互作用能之间的密切平衡，这最终控制了在某些情况下观察到的异常选择性。
• Rhodium(II) Catalyzed Cyclization of Diazo Thiocarbonyl Compounds for Heterocycloic Synthesis
  作者：Albert Padwa、Frederic R. Kinder、William R. Nadler、Lin Zhi

  DOI：10.3987/com-92-s29

  日期：——

  The mesoionic thioisomunchnone system was prepared from the rhodium(II) acetate catalyzed cyclization of a diazothioamide and was found to undergo smooth 1,3-dipolar cycloaddition with N-phenylmaleimide. In contrast to this system, the rhodium(II) reaction of an alpha-diazo-beta-oxo ester containing a thiocarbonyl group produced a cyclic thiocarbonyl ylide which extruded sulfur from a transient episulfide intermediate.
• Dakin-West Reaction of N-Thioacylprolines Using Trifluoroacetic Anhydride: Novel Access to 5-Trifluoromethylthiazoles
  作者：Masami Kawase、Yuri Hagimoto、Ryosuke Saijo

  DOI：10.3987/com-13-12904

  日期：——

  The reaction between N-thioacylprolines and trifluoro acetic anhydride in the presence of pyridine afforded a good yield of 5-trifluoromethylthiazoles. This reaction proceeded through mesoionic 1,3-thiazolium-5-olates, followed by cleavage of the pyrrolidine ring and the formation of thiazoles, introducing a trifluoromethyl group at position 5 in the thiazole ring.