(S)-methyl 2-(2-formyl-1H-pyrrol-1-yl)-2-phenylacetate | 918165-03-4

• 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: (S)-methyl 2-(2-formyl-1H-pyrrol-1-yl)-2-phenylacetate
• CAS: 918165-03-4
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: XZKBCGXEJGRBRX-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  48.3
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-(2-formyl-1H-pyrrol-1-yl)-2-phenylacetate 、 去甲麻黄碱 以 苯 为溶剂， 以73%的产率得到(2R,3S,6S,10bR)-2,6-diphenyl-3-methyl-2,3-dihydro-10bH-[1,3]oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-5(6H)-one
  参考文献：
  名称：

  Intermolecular one-pot cyclization of formyl-pyrroles of amino acid esters with norephedrine: stereoselective routes to new tricyclic pyrrole–pyrazine–oxazole fused structures

  摘要：

  The treatment of esters of amino acids with dimethoxytetrahydrofuran furnished pyrrole derivatives of amino acid esters. The Wilsmeier-Haack formylation followed by the reaction of the formylated pyrroles with norephedrine afforded a selective formation of the tricyclic pyrrole-pyrazine-oxazole fused structures in one step via the formation of an oxazoline structure and intramolecular lactam formation. Pyrrole-pyrazine-oxazole fused structures were achieved in good yields. The cyclization reaction for the formation of an oxazole ring worked selectively to form only one stereoisomer. The configuration of the newly generated stereogenic center in the oxazole ring is dependent on the stereogenic centers of norephedrine. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.09.020
• 作为产物：
  描述：

  甲基2-(苯基氨基)乙酸酯 在 溶剂黄146 、 三氯氧磷 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 3.5h， 生成 (S)-methyl 2-(2-formyl-1H-pyrrol-1-yl)-2-phenylacetate
  参考文献：
  名称：

  Intermolecular one-pot cyclization of formyl-pyrroles of amino acid esters with norephedrine: stereoselective routes to new tricyclic pyrrole–pyrazine–oxazole fused structures

  摘要：

  The treatment of esters of amino acids with dimethoxytetrahydrofuran furnished pyrrole derivatives of amino acid esters. The Wilsmeier-Haack formylation followed by the reaction of the formylated pyrroles with norephedrine afforded a selective formation of the tricyclic pyrrole-pyrazine-oxazole fused structures in one step via the formation of an oxazoline structure and intramolecular lactam formation. Pyrrole-pyrazine-oxazole fused structures were achieved in good yields. The cyclization reaction for the formation of an oxazole ring worked selectively to form only one stereoisomer. The configuration of the newly generated stereogenic center in the oxazole ring is dependent on the stereogenic centers of norephedrine. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.09.020

文献信息

• Synthesis of Enantiopure Highly Functionalized Pyrrolizines and Indolizines from Natural α-Amino Acids: An Ex­perimental and Theoretical Investigation
  作者：Elena Borsini、Gianluigi Broggini、Alessandro Contini、Gaetano Zecchi

  DOI：10.1002/ejoc.200701217

  日期：2008.6

  Variously substituted enantiopure 2-benzylamino-1-hydroxymethyl-2,3-dihydro-1H-pyrrolizines and 6-benzylamino-5,6,7,8-tetrahydroindolizin-8-ols have been prepared. The reaction sequence starts from L-α-amino acids and involves an intramolecular cycloaddition of pyrrole-based nitrone intermediates. A theoretical investigation at the HCTH/6-311+G(d,p)//HCTH/6-31+G(d) level of theory was performed with

  已经制备了各种取代的对映体纯 2-benzylamino-1-hydroxymethyl-2,3-dihydro-1H-pyrrolizines 和 6-benzylamino-5,6,7,8-tetrahydroindolizin-8-ols。反应序列从 L-α-氨基酸开始，涉及基于吡咯的硝酮中间体的分子内环加成。在 HCTH/6-311+G(d,p)//HCTH/6-31+G(d) 理论水平上进行了理论研究，目的是使取代基对环加成反应区域化学的影响合理化.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)