(2S)-Ethyl-5-ethoxy-3,4-dihydro-2H-pyrrol-2-carboxylat | 76529-79-8

• 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)-Ethyl-5-ethoxy-3,4-dihydro-2H-pyrrol-2-carboxylat
• 英文别名: ethyl (2S)-5-ethoxy-3,4-dihydro-2H-pyrrole-2-carboxylate；L-2-ethoxy-5-carbethoxy-1-pyrroline；(S)-ethyl 5-Ethoxy-3,4-dihydro-2H-pyrrole-2-carboxylate
• CAS: 76529-79-8
• 化学式: C₉H₁₅NO₃
• 分子量: 185.223
• InChiKey: CHHBRBKLDYAWRV-ZETCQYMHSA-N

物化性质

• 沸点：
  243.2±33.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-Ethyl-5-ethoxy-3,4-dihydro-2H-pyrrol-2-carboxylat 在 三乙胺 、 三氟乙酸 、 三氯化磷 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 生成 ethyl (3S)-6-chloroacetylamino-8-cyano-5-oxo-1,2,3,5,6,7-hexahydroindolizine-3-carboxylate
  参考文献：
  名称：

  An interesting dichotomy in the cyclisation of exocyclic enamines with protected dehydroamino acids leading to different β-turn templates

  摘要：

  Two templates for the preparation of external beta-turns have been synthesised. In the course of the synthetic studies an interesting dichotomy was observed in the PCl3 catalysed reaction of exocyclic enamines such as 6 and 14 with protected dehydroamino acids. When amide protected dehydroamino acids were condensed with 6 and 14 the expected 6/6 and 6/5 fused bicyclic compounds such as 7 and 15 respectively were obtained, whereas when urethane protected dehydroamino acids were used, the 5/6 and 5/5 fused products 9 and 18 were obtained.(C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02141-x
• 作为产物：
  描述：

  triethyloxonium fluoroborate 、 L-焦谷氨酸乙酯 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以97%的产率得到(2S)-Ethyl-5-ethoxy-3,4-dihydro-2H-pyrrol-2-carboxylat
  参考文献：
  名称：

  酰亚胺化物的合成：使用Meerwein试剂的TFA介导的区域选择性酰胺烷基化

  摘要：

  酰胺的区域选择性O-烷基化以形成相应的亚氨酸酯是常见的合成问题，通常导致N-烷基化量的变化。筛选将酰胺转化为酰亚胺的现有方法得出的结果不一致或不可重现，有时会以N-烷基酰胺为主要产物。设计了一种具有完全区域选择性的简单而可靠的酰胺O-烷基化方案，并在许多底物上证明了其范围和效率。

  DOI：

  10.1021/acs.joc.6b00424

文献信息

• オートタキシン阻害活性を有する縮環ピリミジノン誘導体
  申请人：塩野義製薬株式会社

  公开号：JP2017149693A

  公开（公告）日：2017-08-31

  【課題】優れたオートタキシン阻害活性を有する縮環ピリミジノン誘導体の提供。【解決手段】下記式等で例示される化合物またはその製薬上許容される塩。【選択図】なし

  提供具有优秀自动抑制活性的缩环嘧啶酮衍生物。采用下述式所示的化合物或其在药学上可接受的盐。【选择图】无
• Intramolecular aminolysis of esters. O-Acetylserine and .gamma.-esters of glutamic acid
  作者：Michael Caswell、Rama K. Chaturvedi、Stuart M. Lane、Bina Zvilichovsky、Gaston L. Schmir

  DOI：10.1021/jo00321a011

  日期：1981.4
• Synthesis of external β-turn templates by reaction of protected dehydroamino acids with cyclic enaminoesters
  作者：Jane M. Berry、Paul M. Doyle、Douglas W. Young

  DOI：10.1016/j.tet.2004.09.036

  日期：2005.1

  Two external beta-turn templates have been synthesised and one of them has been derivatised as a GLDV-tetrapeptide. In the course of the synthesis an interesting dichotomy was observed in the condensation of exocyclic enamines such as 4 and 19 with protected dehydroamino acids using phosphorus trichloride. When dehydroamido acids were condensed with the enamines 4 and 19 then 6/6 and 6/5 fused bicyclic compounds such as 5 and 20, respectively, were obtained, whereas, when dehydroamino acid urethanes were used, the 5/6 and 5/5 fused products 7 and 23 were obtained. The bicyclic template 20 was converted to the GLDV-tetrapeptide derivative 31 but the sensitivity to base of the acyl-enamine system of the template reduced the yield in the synthesis of the external turn 35. (C) 2004 Elsevier Ltd. All rights reserved.
• Saalfrank, Rolf W.; Struck, Oliver; Peters, Karl, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1994, vol. 49, # 10, p. 1415 - 1424
  作者：Saalfrank, Rolf W.、Struck, Oliver、Peters, Karl、Schnering, Hans Georg von

  DOI：——

  日期：——
• Synthesis of Imidates: TFA-Mediated Regioselective Amide Alkylation Using Meerwein’s Reagent
  作者：Kirill Popov、Peter Somfai

  DOI：10.1021/acs.joc.6b00424

  日期：2016.4.15

  Regioselective O-alkylation of an amide to form the corresponding imidate is a common synthetic problem, often resulting in varying amounts of N-alkylation. Screening existing methods for converting amides to imidates gave inconsistent or irreproducible results, sometimes affording N-alkylamide as the major product. A simple and reliable protocol for amide O-alkylation with complete regioselectivity

  酰胺的区域选择性O-烷基化以形成相应的亚氨酸酯是常见的合成问题，通常导致N-烷基化量的变化。筛选将酰胺转化为酰亚胺的现有方法得出的结果不一致或不可重现，有时会以N-烷基酰胺为主要产物。设计了一种具有完全区域选择性的简单而可靠的酰胺O-烷基化方案，并在许多底物上证明了其范围和效率。