Ethyl (2R,3R,4R,5S)-4-acetyl-3-<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>-5-phenylpyrrolidine-2-carboxylate | 153186-39-1

• 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: Ethyl (2R,3R,4R,5S)-4-acetyl-3-<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>-5-phenylpyrrolidine-2-carboxylate
• 英文别名: ethyl (2R,3R,4R,5S)-4-acetyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-phenylpyrrolidine-2-carboxylate
• CAS: 153186-39-1
• 化学式: C₂₀H₂₇NO₅
• 分子量: 361.438
• InChiKey: MUFNSPJUQGEQCO-DUQPFJRNSA-N

物化性质

• 沸点：
  470.2±45.0 °C(predicted)
• 密度：
  1.139±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl (2R,3R,4R,5S)-4-acetyl-3-<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>-5-phenylpyrrolidine-2-carboxylate 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以81%的产率得到Ethyl (2R,3R,4R,5S)-4-acetyl-3-<(1S)-1,2-dihydroxyethyl>-5-phenylpyrrolidine-2-carboxylate
  参考文献：
  名称：

  Polyfunctionalized Pyrrolidines by Stereoselective 1,3-Dipolar Cycloaddition of Azomethine Ylides to Chiral Enones

  摘要：

  The cycloaddition reactions of chiral alpha,beta-unsaturated ketones substituted by alkoxy or amino groups in the gamma-position to azomethine ylides (obtained from glycine imines) were investigated in the presence of a base, LiBr and AgOAc. High regioselectivities were observed in most cases, resulting in the formation of a single diastereomer, particularly if a DBU/AgOAc catalyst system was employed. The influence of reaction conditions and olefin structure on the stereoselectivity of the reaction was investigated, and models rationalizing stereocontrol are proposed. In addition, an interesting deconjugation reaction of acetals derived from gamma,delta-dihydroxy alpha,beta-unsaturated enones or esters is described.

  DOI：

  10.1021/jo00121a019
• 作为产物：
  描述：

  (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 silver(I) acetate 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 4.0h， 生成 Ethyl (2R,3R,4R,5S)-4-acetyl-3-<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>-5-phenylpyrrolidine-2-carboxylate
  参考文献：
  名称：

  对映体纯的吡咯烷类化合物通过偶氮甲亚胺与烯酮的立体定向环加成反应合成

  摘要：

  在DBU / AgOAc的存在下，几种在γ位带有手性烷氧基或氨基取代基的（E）-α，β-不饱和酮（烯酮）2与偶氮甲亚胺3（由甘氨酸亚胺获得）反应，得到对映体纯的吡咯烷衍生物4以立体定向的方式。

  DOI：

  10.1016/s0040-4039(00)73839-1

文献信息

• Polyfunctionalized Pyrrolidines by Stereoselective 1,3-Dipolar Cycloaddition of Azomethine Ylides to Chiral Enones
  作者：Guido Galley、Juergen Liebscher、Michael Paetzel

  DOI：10.1021/jo00121a019

  日期：1995.8

  The cycloaddition reactions of chiral alpha,beta-unsaturated ketones substituted by alkoxy or amino groups in the gamma-position to azomethine ylides (obtained from glycine imines) were investigated in the presence of a base, LiBr and AgOAc. High regioselectivities were observed in most cases, resulting in the formation of a single diastereomer, particularly if a DBU/AgOAc catalyst system was employed. The influence of reaction conditions and olefin structure on the stereoselectivity of the reaction was investigated, and models rationalizing stereocontrol are proposed. In addition, an interesting deconjugation reaction of acetals derived from gamma,delta-dihydroxy alpha,beta-unsaturated enones or esters is described.
• Synthesis of enantiomerically pure pyrrolidines by stereospecific cycloaddition of azomethine ylides with enones
  作者：M. Pätzel、G. Galley、P.G. Jones、A. Chrapkowsky

  DOI：10.1016/s0040-4039(00)73839-1

  日期：1993.9

  alkoxy or amino substituent in γ-position react with azomethine ylides 3 (obtained from glycine imines) in the presence of DBU/AgOAc giving enantiomerically pure pyrrolidine derivatives 4 in a stereospecific manner.

  在DBU / AgOAc的存在下，几种在γ位带有手性烷氧基或氨基取代基的（E）-α，β-不饱和酮（烯酮）2与偶氮甲亚胺3（由甘氨酸亚胺获得）反应，得到对映体纯的吡咯烷衍生物4以立体定向的方式。