Z-ethyl 3-oxo-2-(2-pyridyl)methylenebutanoate | 63272-89-9

• 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: Z-ethyl 3-oxo-2-(2-pyridyl)methylenebutanoate
• 英文别名: α-pyridylmethylideneacetoacetic acid ethyl ester；Z-2-(2-Pyridylmethylen)-acetessigsaeure-ethylester；(E)-Ethyl 3-oxo-2-(pyrid-2-yl)methylene-butanoate；ethyl (2Z)-3-oxo-2-(pyridin-2-ylmethylidene)butanoate
• CAS: 63272-89-9
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: JCGPGDXPKWXSCR-FLIBITNWSA-N

物化性质

• 熔点：
  85-87 °C
• 沸点：
  341.3±27.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

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：

  Z-ethyl 3-oxo-2-(2-pyridyl)methylenebutanoate 在 盐酸 作用下， 以 氯仿 为溶剂， 生成 2-Ethoxycarbonyl-3-hydroxy-3-methyl-3H-indolizinylium; chloride
  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
• 作为产物：
  描述：

  吡啶-2-甲醛 、 乙酰乙酸乙酯 生成 Z-ethyl 3-oxo-2-(2-pyridyl)methylenebutanoate
  参考文献：
  名称：

  Replacement Substituent Constants for Simple Heterocycles

  摘要：

  DOI：

  10.1016/s0040-4020(01)81306-5

文献信息

• Pharmaceutical compositions containing unsymmetrical esters of
  申请人：Farbenfabriken Bayer AG

  公开号：US03932645A1

  公开（公告）日：1976-01-13

  Pharmaceutical compositions containing unsymmetrical esters of 1,4-dihydropyridine 3,5-dicarboxylic acids as the active ingredient and methods of using same. The said ingredients are unsymmetrical 1,4-dihydropyridine 3,5-dicarboxylates which are substituted at position-4 of the dihydropyridine nucleus by phenyl which contains at least one nitro, cyano, azido, alkylthio, or alkylsulphonyl substituent. The compositions have a cardiovascular activity which makes them useful for effecting coronary vascular dilation and, also, they have utility in the treatment of hypertension.

  含有不对称酯化的1,4-二氢吡啶-3,5-二羧酸的药物组合物作为活性成分，并使用方法。所述成分是在二氢吡啶核的4位被苯基取代的不对称1,4-二氢吡啶-3,5-二羧酸酯，该苯基含有至少一个硝基、氰基、叠氮基、烷基硫醚或烷基磺酰基取代基。这些组合物具有心血管活性，可用于促进冠状血管扩张，并且在治疗高血压方面具有用途。
• POHJALA E. K., J. HETEROCYCL. CHEM. <JHTC-AD>, 1977, 14, NO 2, 273-279
  作者：POHJALA E. K.

  DOI：——

  日期：——
• ENDERS, DIETER;MULLER, STEPHAN;DEMIR, AYHAN S., TETRAHEDRON LETT., 29,(1988) N 49, C. 6437-6440
  作者：ENDERS, DIETER、MULLER, STEPHAN、DEMIR, AYHAN S.

  DOI：——

  日期：——
• US3939171A
  申请人：——

  公开号：US3939171A

  公开（公告）日：1976-02-17
• US3946026A
  申请人：——

  公开号：US3946026A

  公开（公告）日：1976-03-23