E-ethyl 3-oxo-2-(2-pyridyl)methylenebutanoate | 63272-90-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: E-ethyl 3-oxo-2-(2-pyridyl)methylenebutanoate
• 英文别名: E-2-(2-Pyridylmethylen)-acetessigsaeure-ethylester；ethyl (2E)-3-oxo-2-(pyridin-2-ylmethylidene)butanoate
• CAS: 63272-90-2
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: JCGPGDXPKWXSCR-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  E-ethyl 3-oxo-2-(2-pyridyl)methylenebutanoate 以13%的产率得到
  参考文献：
  名称：

  BINIECKI, S.;KABZINSKA, Z.;KRZEMINSKI, J., ACTA POL. PHARM., 1981, 38, N 3, 297-300

  摘要：

  DOI：
• 作为产物：
  描述：

  Z-ethyl 3-oxo-2-(2-pyridyl)methylenebutanoate 在 盐酸 、 碳酸氢钠 作用下， 以 氯仿 为溶剂， 生成 E-ethyl 3-oxo-2-(2-pyridyl)methylenebutanoate
  参考文献：
  名称：

  Electron impact mass spectra of 2-(2-pyridyl)methylene-1,3-dicarbonyl compounds: Unusual abundance of the [M + 1]+ ion and the effect of stereochemistry

  摘要：

  AbstractElectron impact mass spectra of 2‐(2‐pyridyl)methylene‐1,3‐dicarbonyl compounds and related heteroaryl species have been investigated. In 3‐(2‐pyridyl)methylene‐2,4‐pentanedione, its 6′‐methyl and 6′‐methoxycarbonyl derivatives and in E‐ and Z‐ethyl 3‐oxo‐2‐(2‐pyridyl)methylenebutanoates the base peak arises from the loss of methyl radical from the molecular ion to produce a 3‐oxo‐3H‐indolizinium ion. A marked difference is observed in the behaviour of the geometric isomers of the keto esters. The diketones and E‐keto ester carrying a 2‐pyridyl substituent and ketone functionality on the same side of the carbon‐carbon double bond exhibit an unusually high [M + 1]+/[M]+˙ ratio (about 2.5) under normal ionization conditions (pressure 10–100 μPa). This abnormality is a function of pressure only and independent of temperature. In the case of the Z‐keto ester, the corresponding malonate, 3‐ and 4‐(2‐pyridyl)methylene‐2,4‐pentanediones, and 2‐furyl, 2‐thienyl and phenyl diketone analogues, the ratio does not differ much from that due to the natural isotope abundance. Results for 1,1,1,5,5,5‐hexadeuterio‐2‐(2‐pyridyl)‐methylene‐2,4‐pentanedione (strong M + 2 peak) suggest one mass unit transfer as an intermolecular proton shift from a methyl group to give a 3‐hydroxy‐3‐methyl‐3H‐indolizinium ion. This real mass spectrometric phenomenon is a unique example of low pressure self‐chemical ionization.

  DOI：

  10.1002/oms.1210161203

文献信息

• Replacement Substituent Constants for Simple Heterocycles
  作者：Charles N. Robinson、Leonard J. Wiseman、Carl D. Slater

  DOI：10.1016/s0040-4020(01)81306-5

  日期：1989.1
• POHJALA E. K., FINN. CHEM. LETT., 1980, NO 4, 126-128
  作者：POHJALA E. K.

  DOI：——

  日期：——
• BINIECKI, S.;KRZEMINSKI, J., ACTA POL. PHARM., 1985, 42, N 2, 109-111
  作者：BINIECKI, S.、KRZEMINSKI, J.

  DOI：——

  日期：——
• SPRAKE J. M.; WATSON, K. D., J. CHEM. SOC. PERKIN TRANS., PART1 <JCPK-BH>, 1976, NO 1, 5-8
  作者：SPRAKE J. M.、 WATSON, K. D.

  DOI：——

  日期：——
• POHJALA E. K., J. HETEROCYCL. CHEM. <JHTC-AD>, 1977, 14, NO 2, 273-279
  作者：POHJALA E. K.

  DOI：——

  日期：——