α-(Tetrahydropyrrolylidene-2) acetate d'ethyle | 108139-96-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: α-(Tetrahydropyrrolylidene-2) acetate d'ethyle
• 英文别名: ethyl pyrrolidin-2-ylideneacetate；Ethyl 2-(pyrrolidin-2-ylidene)acetate；ethyl (2E)-2-pyrrolidin-2-ylideneacetate
• CAS: 108139-96-4
• 化学式: C₈H₁₃NO₂
• 分子量: 155.197
• InChiKey: LHJWLENSDKDMPJ-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-(Tetrahydropyrrolylidene-2) acetate d'ethyle 在 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 8.75h， 生成 ethyl 1,2-dihydro-3H-pyrrolizine-7-carboxylate
  参考文献：
  名称：

  Synthesis of 2,3-Dihydropyrrolizines from Weinreb 3-(Pyrrolidin-2-ylidene­)propionamides or WeinrebN-Vinylprolinamides

  摘要：

  Weinreb 3-(吡咯烷-2-亚基)丙酰胺和Weinreb N-乙烯基脯氨酰胺被用于合成2,3-二氢吡咯嗪。羧酰胺基团与有机金属化合物的选择性反应使我们能够获得多种类似于Hantzsch和Knorr吡咯合成中的羰基中间体，这些中间体在热力作用下环化。

  DOI：

  10.1055/s-2002-35220
• 作为产物：
  描述：

  2,2-二甲基-5-(2-四氢吡咯亚基 、 乙醇 以98%的产率得到
  参考文献：
  名称：

  CELERIER J. P.; LHOMMET G.; MAITTE P., TETRAHEDRON LETT., 1981, 22, NO 10, 963-964

  摘要：

  DOI：

文献信息

• “Conformationally restricted β-amino acid isosteres prepared through regioselectively controlled aza-annulation.”
  作者：K. Paulvannan、John R. Stille

  DOI：10.1016/s0040-4039(00)61389-8

  日期：1993.12

  A variety of electron withdrawing substituents were used to enhance the aza-annulation of enamines with acryloyl chloride, to direct the regioselectivity of alkene formation, and to facilitate hydrogenation of the unsaturated annulation product. The resulting δ-lactam products were β-amino acid analogs with structural features similar to those of established peptide isosteres.

  多种吸电子取代基用于增强烯胺与丙烯酰氯的氮杂-环氧化，以指导烯烃形成的区域选择性，并促进不饱和环化产物的氢化。所得的δ-内酰胺产物是β-氨基酸类似物，其结构特征与已建立的肽等排物相似。
• Bicyclic triazoles from a diazo transfer reaction between cyclic enaminones and 5,7-dinitro-3-diazo-1,3-dihydro-2H-indol-2-one
  作者：Rodinei Augusti、Concetta Kascheres

  DOI：10.1016/s0040-4020(01)81328-4

  日期：1994.1

  The synthetic usefulness of a new method of 1,2,3-triazole synthesis has been demonstrated. By employing cyclic enamino esters 3 and enamino ketones 4 in reactions with 5,7-dinitro-3-diazo-1,3-dihydro-2H-indol-2-one (1), bicyclic triazoles 5 and 6 have been prepared in good to excellent yields.

  已经证明了1,2,3-三唑合成新方法的合成有用性。通过与5，7-二硝基-3-重氮-1，3-二氢-2H-吲哚-2-酮（1）反应使用环状烯氨基酯3和烯氨基酮4，良好地制备了双环三唑5和6。达到优异的产量。
• Heterocycle Formation through Aza-Annulation: Stereochemically Controlled Syntheses of (.+-.)-5-Epitashiromine and (.+-.)-Tashiromine
  作者：K. Paulvannan、John R. Stille

  DOI：10.1021/jo00086a009

  日期：1994.4

  N-alkylenamines, stabilized through conjugation with an electron-withdrawing group, undergo aza-annulation with acryloyl chloride to provide a convergent route for the construction of six-membered nitrogen heterocycles. In addition to enhancing the C-alkylation process of annulation relative to the competing N-acylation process, the electron withdrawing substituent controlled the regioselectivity of alkene formation in both the intermediate enamine and in the unsaturated lactam product. A variety of functional groups, which include -COMe, -COPh, -CO(2)R, -CONHPh, -CN, -P(O)(OEt)(2), and -SO(2)Ph, were used to determine the effect of the electron-withdrawing substituents upon both the annulation reaction with acryloyl chloride and the subsequent hydrogenation process. When the enamide annulation product was stabilized through conjugation with ester or amide substituents, catalytic hydrogenation of the ate-annulation product resulted in the formation of vicinal stereocenters with high cis selectivity. The utility of this methodology was demonstrated by application of the condensation/aza-annulation/hydrogenation sequence as the key for construction and stereochemical control of the indolizidine ring system of (+/-)-tashiromine.
• Brunerie, Pascal; Celerier, Jean-Pierre; Petit, Huguette, Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 1183 - 1188
  作者：Brunerie, Pascal、Celerier, Jean-Pierre、Petit, Huguette、Lhommet, Gerard

  DOI：——

  日期：——
• CELERIER J.-P.; DELOISY E.; LHOMMET G.; MAITTE P., J. ORG. CHEM., 1979, 44, NO 17, 3089
  作者：CELERIER J.-P.、 DELOISY E.、 LHOMMET G.、 MAITTE P.

  DOI：——

  日期：——