3-(2-pyridyl)methylene-2,4-pentanedione | 63272-88-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(2-pyridyl)methylene-2,4-pentanedione
• 英文别名: 3-(pyridine-2-yl-methylene)pentane-2,4-dione；1--2,2-diacetylethylen；3-(2-Pyridylmethylen)-acetylaceton；3-pyridin-2-ylmethylene-pentane-2,4-dione；3-[2]pyridylmethylene-pentane-2,4-dione；3-[2]Pyridylmethylen-pentan-2,4-dion；2,4-Pentanedione, 3-(2-pyridylmethylene)-, hydrate；3-(pyridin-2-ylmethylidene)pentane-2,4-dione
• CAS: 63272-88-8
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: RPPHOMQYXZMNPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  47
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-pyridyl)methylene-2,4-pentanedione 在 氢气 作用下， 生成 2-(2,2-Diacetylethyl)-pyridin
  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 、 乙酰丙酮 在 哌啶 作用下， 生成 3-(2-pyridyl)methylene-2,4-pentanedione
  参考文献：
  名称：

  Kuhn; Hensel, Chemische Berichte, 1953, vol. 86, p. 1333,1337

  摘要：

  DOI：

文献信息

• Reaction of Corey Ylide with α,β-Unsaturated Ketones: Tuning of Chemoselectivity toward Dihydrofuran Synthesis
  作者：Alexey O. Chagarovsky、Ekaterina M. Budynina、Olga A. Ivanova、Elena V. Villemson、Victor B. Rybakov、Igor V. Trushkov、Mikhail Ya. Melnikov

  DOI：10.1021/ol500877c

  日期：2014.6.6

  A straightforward, efficient, and reliable approach to synthetically valuable 2,3-dihydrofurans via a reaction between Corey ylide and α,β-unsaturated ketones has been developed. The use of simple and widely spread starting materials as well as mild reaction conditions and scalability provide a broad scope of 2,3-dihydrofurans.

  通过Corey ylide与α，β-不饱和酮之间的反应，开发了一种合成有价值的2,3-二氢呋喃的简单，有效和可靠的方法。简单且广泛分布的起始原料的使用以及温和的反应条件和可扩展性提供了广泛的2,3-二氢呋喃范围。
• Oxidative Coordination versus C ³ −C(O)Me Bond Cleavage in Acetylacetonate Iridium Complexes
  作者：Christopher E. Rivas、Jose C. Alvarado‐Monzon、Gerardo Gonzalez‐Garcia、J. Oscar C. Jimenez‐Halla、Jesus Rangel‐Garcia、Crispin Cristobal、Jorge A. Lopez

  DOI：10.1002/chem.202100709

  日期：2021.6.10

  been achieved in the reaction with [Ir(Cl)(dmb)2] (dmb=2,3-dimethylbutadiene), yielding a compound formulated as [Irκ2-N,C-(pyC(H)C(C(O)Me))}(CO)(μ-Cl)(Me)]2, 2. Treatment of dimer 2 with DMSO or PMe3 produced the complexes[Irκ2-N,C-(pyC(H)C(C(O)Me)}(CO)Cl(Me)L] (L=DMSO, 3 a; PMe3, 3 b). Plausible mechanisms for the reactions leading to complexes 1 and 2 are proposed by means of DFT calculations.

  Iridabicycles [Irκ 3 -N,C,O-(pyC(H)=C(C(O)Me) 2 }(Cl)(L−L)](L−L=cod (cod=1,5 -环辛二烯), 1 a ; bipy (bipy=2,2'- bipyridine), 1 b ) 已通过 3-(pyridine-2-yl-methylene)pentane-2,4-dione L1的氧化配位获得，以复合物 [Ir(μ-Cl)(cod)} 2 ] 和 [Ir(μ-Cl)(coe) 2 } 2 ] (coe= cis -cyclooctene)，后者在 bipy 的存在下。值得注意的是，L1的 C 3 -C(O)Me 键的裂解是在与 [Ir(Cl)(dmb) 2 ] (dmb=2,3-二甲基丁二烯) 的反应中实现的，产生一种化合物 [Ir κ2 -N,C-(pyC(H)C(C(O)Me))}(CO)(μ-Cl)(Me)]
• 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：——
• POHJALA E. K., J. HETEROCYCL. CHEM. <JHTC-AD>, 1977, 14, NO 2, 273-279
  作者：POHJALA E. K.

  DOI：——

  日期：——