(E)-5-<(methoxycarbonyl)methylidene>-2-pyrrolidinone | 135145-13-0

• 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: (E)-5-<(methoxycarbonyl)methylidene>-2-pyrrolidinone
• 英文别名: methyl (2E)-2-(5-oxopyrrolidin-2-ylidene)acetate
• CAS: 135145-13-0
• 化学式: C₇H₉NO₃
• 分子量: 155.153
• InChiKey: RHHTYVUIIXBMPB-SNAWJCMRSA-N

物化性质

• 沸点：
  348.4±42.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-5-<(methoxycarbonyl)methylidene>-2-pyrrolidinone 、 甲醇 以95%的产率得到
  参考文献：
  名称：

  GOSSAUER A.; ROESSLER F.; ZILCH H., LIEBIGS ANN. CHEM., 1979, NO 9, 1309-1321

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z)-5-<(methoxycarbonyl)methylidene>-2-pyrrolidinone 在 silica gel 作用下， 生成 (E)-5-<(methoxycarbonyl)methylidene>-2-pyrrolidinone
  参考文献：
  名称：

  The reaction of thioimides with phosphorus ylides

  摘要：

  The reaction of a series of thioimides with phosphorus ylides, in a manner analogous to the Wittig reaction, has been examined. The resulting reaction products represent potentially valuable intermediates in tetrapyrrole pigment synthesis. In addition to the desired thio-Wittig-type coupling reaction, the presence of two competing reaction pathways, S-alkylation and oxidation/reduction, has been observed with certain substrates. These empirical observations have been correlated to theoretical data, derived from MNDO and ab initio calculations, which delineate the structure-reactivity relationships governing product distribution from the various reaction pathways. A detailed analysis is presented of the mechanisms of the thio-Wittig coupling reaction and the competitive S-alkylation reaction.

  DOI：

  10.1021/jo00017a017

文献信息

• Studies on the Synthesis of Phytochrome and Related Tetrapyrroles. Dihydropyrromethenones by Photochemical Rearrangement of <i>N</i>-Pyrrolo Enamides
  作者：Peter A. Jacobi、Subhas C. Buddhu、Douglas Fry、S. Rajeswari

  DOI：10.1021/jo970288j

  日期：1997.5.1

  precursor for the synthesis of phytochrome 1, has been prepared in enantiomerically pure form beginning with N-aminopyrrole 64 and the acetylenic acid 62b. The key step involved a 3,5-sigmatropic rearrangement of N-pyrrolo enamide 66b.

  从N-氨基吡咯64和炔酸62b开始，以对映体纯的形式制备了二氢吡咯烷酮67b，其是合成植物色素1的潜在前体。关键步骤涉及N-吡咯烷酰胺66b的3,5-σ重排。
• Toward the Synthesis of Biologically Important Chlorins, Isobacteriochlorins, and Corrins. Cyclic Enamides from Acetylenic Amides
  作者：Peter A. Jacobi、Harry L. Brielmann、Sheila I. Hauck

  DOI：10.1021/jo960428+

  日期：1996.1.1

  Cyclic enamides 1 of a type useful in the synthesis of naturally occurring chlorins, isobacteriochlorins, and corrins have been prepared by a process involving 5-exo-dig cyclization of the appropriate acetylenic amides 11. The desired cyclization is catalyzed by either n-Bu(4)NF or LiAl-(NHBn)(4).
• JACOBI, PETER A.;BUDDHU, SUBHAS C., TETRAHEDRON LETT., 29,(1988) N 38, C. 4823-4826
  作者：JACOBI, PETER A.、BUDDHU, SUBHAS C.

  DOI：——

  日期：——
• CELERIER, J. P.;MARX, E.;LHOMMET, G., J. HETEROCYCL. CHEM., 25,(1988) N 4, C. 1275-1276
  作者：CELERIER, J. P.、MARX, E.、LHOMMET, G.

  DOI：——

  日期：——
• The reaction of thioimides with phosphorus ylides
  作者：John E. Bishop、John F. O'Connell、Henry Rapoport

  DOI：10.1021/jo00017a017

  日期：1991.8

  The reaction of a series of thioimides with phosphorus ylides, in a manner analogous to the Wittig reaction, has been examined. The resulting reaction products represent potentially valuable intermediates in tetrapyrrole pigment synthesis. In addition to the desired thio-Wittig-type coupling reaction, the presence of two competing reaction pathways, S-alkylation and oxidation/reduction, has been observed with certain substrates. These empirical observations have been correlated to theoretical data, derived from MNDO and ab initio calculations, which delineate the structure-reactivity relationships governing product distribution from the various reaction pathways. A detailed analysis is presented of the mechanisms of the thio-Wittig coupling reaction and the competitive S-alkylation reaction.