(2S,3R,4S,5S)-methyl 3-(4-methoxyphenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate | 888330-67-4

• 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,5S)-methyl 3-(4-methoxyphenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate
• 英文别名: 2-(methoxycarbonyl)-3-(4-methoxyphenyl)-4-nitro-5-phenylpyrrolidine；methyl (2S,3R,4S,5S)-3-(4-methoxyphenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate
• CAS: 888330-67-4
• 化学式: C₁₉H₂₀N₂O₅
• 分子量: 356.378
• InChiKey: CMWZNQXMBDRZHR-OWSLCNJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5S)-methyl 3-(4-methoxyphenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate 、 (2S,3S,4R,5S)-methyl 3-(4-methoxyphenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate 在 manganese(IV) oxide 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 48.0h， 生成 methyl 3-(4-methoxyphenyl)-5-phenyl-1H-pyrrole-2-carboxylate 、 5-phenyl-3-(4-methoxyphenyl)-2-methoxycarbonyl-4-nitro-1H-pyrrole
  参考文献：
  名称：

  NOVEL PYRROLE DERIVATIVES WITH HISTONE DEACETYLASE INHIBITOR ACTIVITY

  摘要：

  公开号：

  EP1975158B9
• 作为产物：
  描述：

  苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 silver(I) acetate 、 magnesium sulfate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 20.0h， 生成 (2S,3R,4S,5S)-methyl 3-(4-methoxyphenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate
  参考文献：
  名称：

  Stereocontrolled Synthesis of Highly Substituted Proline Esters via [3 + 2] Cycloaddition between N-Metalated Azomethine Ylides and Nitroalkenes. Origins of the Metal Effect on the Stereochemical Outcome

  摘要：

  The [3 + 2] cycloaddition reaction between several N-metalated azomethine ylides and nitroalkenes has been studied using AgOAc and LiClO4 as metalating reagents in the presence of triethylamine. The reaction is found to be very versatile and can be extended to homochiral nitroalkenes. In general, lithium and silver salts promote preferential formation of the endo and exo cycloadducts, respectively. The presence of a phenol moiety induces a shift toward the exo-cycloadduct even when lithium is used. A model based upon the experimental results obtained and SCF-MO calculations is proposed to explain the variable stereochemical outcome of these reactions.

  DOI：

  10.1021/jo971212q

文献信息

• Catalytic Asymmetric exo′-Selective [3+2] Cycloaddition of Iminoesters with Nitroalkenes
  作者：Takayoshi Arai、Naota Yokoyama、Asami Mishiro、Hiroyasu Sato

  DOI：10.1002/anie.201004098

  日期：2010.10.18

  Under control: A chiral imidazoline–aminophenol/Ni(OAc)2 complex promotes the first catalytic asymmetric exo′‐selective [3+2] cycloaddition of iminoesters and nitroalkenes. Thermodynamic control over the stepwise Michael/Mannich cyclization steps gives the adducts in up to 99 % ee.

  下控制：手性咪唑啉-氨基苯酚/镍（OAC）2络合物促进第一催化不对称外切' -选择性[3 + 2] iminoesters和硝基烯烃的环加成。通过逐步进行Michael / Mannich环化步骤的热力学控制，可以使加合物的ee高达99％  。
• Bifunctional AgOAc/ThioClickFerrophos catalyzed asymmetric 1,3-dipolar cycloaddition reaction of azomethine ylides to nitroalkenes
  作者：Midori Kimura、Yukiko Matsuda、Akihiro Koizumi、Chihiro Tokumitsu、Yuichiro Tokoro、Shin-ichi Fukuzawa

  DOI：10.1016/j.tet.2015.08.002

  日期：2016.5

  AgOAc/ThioClickFerrophos (TCF) complex catalyzed the 1,3-dipolar cycloaddition of azomethine ylides (glycine imino ester) to nitroalkenes. The corresponding endo-cycloadducts (88:12–98:2 endo/exo) were afforded in good yields with high enantioselectivities, up to 98% ee, without addition of external amine. AgOAc/TCF works as a bifunctional (Lewis acid and base) catalyst.

  AgOAc / ThioClickFerrophos（TCF）络合物催化偶氮甲亚胺（甘氨酸亚氨基酯）与硝基烯烃的1,3-偶极环加成反应。相应的内切-cycloadducts（88：12-98：2内型/外型）在具有高对映选择性良好的产率，高达98％ee值被得到，不添加外部胺。AgOAc / TCF可作为双功能（路易斯酸和碱）催化剂。
• Phosphoramidite–Cu(OTf)₂ Complexes as Chiral Catalysts for 1,3-Dipolar Cycloaddition of Iminoesters and Nitroalkenes
  作者：Luis M. Castelló、Carmen Nájera、José M. Sansano、Olatz Larrañaga、Abel de Cózar、Fernando P. Cossío

  DOI：10.1021/ol4006618

  日期：2013.6.21

  Chiral complexes formed by phosphoramidites such as (S-a,R,R)-9 and Cu(OTf)(2) are excellent catalysts for the general 1,3-dipolar cycloaddition between azomethine ylides and nitroalkenes affording the corresponding tetrasubstituted proline esters mainly as exo-cycloadducts in high er at room temperature. The exo-cycloadducts can be obtained in enantiomerically pure form just after simple recrystallization. DFT calculations support the stereochemical results.
• Chiral Bis(imidazolidine)pyridine−Cu(OTf)₂: Catalytic Asymmetric Endo-Selective [3 + 2] Cycloaddition of Imino Esters with Nitroalkenes
  作者：Takayoshi Arai、Asami Mishiro、Naota Yokoyama、Kuniko Suzuki、Hiroyasu Sato

  DOI：10.1021/ja100265j

  日期：2010.4.21

  The novel C-2-symmetric bis(imidazolidine)pyridine (PyBidine) ligand was easily synthesized in a single condensation of 2,6-pyridyl aldehyde and optically active (S,S)diphenylethylenediamine. In the C-2-symmetric PyBidine-Cu(OTf)(2) complex, imidazolidine rings act as "chiral fences" to shield the first and third quadrants. Use of the PyBidine-Cu(OTf)(2) complex as a catalyst enabled the highly endo-selective reaction of imino esters and nitroalkenes to give the adducts in up to 99% ee.
• A Highly Enantio- and Diastereoselective Cu-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with Nitroalkenes
  作者：Xiao-Xia Yan、Qian Peng、Yan Zhang、Kai Zhang、Wei Hong、Xue-Long Hou、Yun-Dong Wu

  DOI：10.1002/anie.200503672

  日期：2006.3.13