(+)-5-naphthalen-2-yl-pyrrolidine-2,4-dicarboxylic acid dimethyl ester | 505075-54-7

• 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: (+)-5-naphthalen-2-yl-pyrrolidine-2,4-dicarboxylic acid dimethyl ester
• 英文别名: (2S,4S, 5R)-dimethyl 5-(2-naphthyl)pyrrolidine-2,4-dicarboxylate；(2S,4S,5R)-dimethyl 5-(naphthalen-2-yl)pyrrolidine-2,4-dicarboxylate；dimethyl (2S,4S,5R)-5-naphthalen-2-ylpyrrolidine-2,4-dicarboxylate
• CAS: 505075-54-7
• 化学式: C₁₈H₁₉NO₄
• 分子量: 313.353
• InChiKey: JPZNQSAKTFJMRE-JYJNAYRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甘氨酸,N-(2-萘基亚甲基)-,甲基酯 、 丙烯酸甲酯（MA） 在 C₃₆H₃₆FeN₃PS 、 silver(I) acetate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以74%的产率得到(+)-5-naphthalen-2-yl-pyrrolidine-2,4-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Ag / ThioClickFerrophos催化偶氮甲亚胺与烯烃的高对映选择性1,3-偶极环加成

  摘要：

  银（I）/ ThioClickFerrophos络合物催化N-亚苄基甘氨酸甲酯（偶氮甲胺基化物的来源）与α，β-不饱和酯和马来酰亚胺的内选择性不对称1,3-偶极环加成反应，得到内基-2,4， 5-和2,3,4,5-取代的吡咯烷具有高收率和高对映选择性（最高99％ee）。该配合物还有效催化了与β-硝基苯乙烯的内选择性反应，从而以高对映选择性得到4-硝基吡咯烷。

  DOI：

  10.1016/j.tetlet.2010.07.085

文献信息

• Chiral Co(II) and Mn(II) catalysts for the 1,3-dipolar cycloaddition reactions of azomethine ylides derived from arylidene imines of glycine
  作者：Philip Allway、Ronald Grigg

  DOI：10.1016/s0040-4039(00)93563-9

  日期：1991.10

  Anhydrous MnBr2 and CoCl2 in conjunction with chiral ephedrine ligands effect substantial asymmetric induction in cycloadducts derived from methyl acrylate and imines of glycine methyl ester. CoCl2 is most effective and gives 96% e.e.

  无水MnBr 2和CoCl 2与手性麻黄碱配体一起在衍生自丙烯酸甲酯和甘氨酸甲酯的亚胺的环加合物中实现了基本的不对称诱导。CoCl 2最有效，可产生96％的ee
• Stereoselective cyclo-addition reactions of azomethine ylides catalysed by in situ generated Ag(I)/bisphosphine complexes
  作者：Ronald Grigg、Suren Husinec、Vladimir Savic

  DOI：10.2298/jsc1001001g

  日期：——

  Stereoselective cyclo-addition reactions of azomethine ylides promoted by in situ generated Ag(I)/bisphosphine complexes were studied. Under the optimized conditions, the pyrrolidine products were isolated in up to 84 % yield and with up to 71% e.e. The effects of various reaction variables on the stereoselectivity were also investigated.

  研究了在原位生成的 Ag(I)/bisphosphine 复合物促进下偶氮甲基酰化物的立体选择性环加成反应。在优化的条件下，分离出的吡咯烷产物收率高达 84%，有效成分高达 71%。
• Enantio- and Diastereoselective [3+2] Cycloadditions of Azomethine Ylides with Ag(I)-Phosphinooxazoline Catalysts
  作者：Andreas Pfaltz、Remo Stohler、Florentine Wahl

  DOI：10.1055/s-2005-865313

  日期：——

  Chiral Ag(I)-phosphinooxazoline (PHOX) complexes are efficient catalysts for [3+2] cycloadditions of azomethine ylides with α,β-unsaturated carboxylic esters. In intramolecular cycloadditions, virtually complete diastereocontrol and enantiomeric excesses of up to 99% have been observed.

  手性 Ag(I)-phosphinooxazoline (PHOX) 复合物是偶氮甲基酰化物与δ,δ-不饱和羧酸酯发生 [3+2] 环加成反应的高效催化剂。在分子内环加成反应中，几乎完全实现了非对映控制，对映体过量率高达 99%。
• A new chiral phosphine oxide ligand for enantioselective 1,3-dipolar cycloaddition reactions of azomethine ylides
  作者：Serap Eröksüz、Özdemir Dogan、Philip P. Garner

  DOI：10.1016/j.tetasy.2010.10.002

  日期：2010.10

  A new set of phosphorus-containing chiral ligands has been synthesized and used with silver(I) for the catalytic asymmetric 1 3-dipolar cycloaddition reaction of azomethine ylides One of these ligands (POFAM6) was found to produce an effective catalyst for the asymmetric 1 3 dipolar cycloaddition reaction of azomethine ylides with electron deficient dipolarophiles to form pyrrolidines in up to 97% yield and 89% (C) 2010 Elsevier Ltd All rights reserved
• Catalytic Asymmetric 1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides—A Simple Approach to Optically Active Highly Functionalized Proline Derivatives
  作者：Aase Sejr Gothelf、Kurt V. Gothelf、Rita G. Hazell、Karl Anker Jørgensen

  DOI：10.1002/1521-3773(20021115)41:22<4236::aid-anie4236>3.0.co;2-w

  日期：2002.11.15