3-methyl-1-(N-piperidino)-1,3-butadiene | 135788-36-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-methyl-1-(N-piperidino)-1,3-butadiene
• 英文别名: 1-[(1E)-3-methylbuta-1,3-dienyl]piperidine
• CAS: 135788-36-2
• 化学式: C₁₀H₁₇N
• 分子量: 151.252
• InChiKey: BMGZXCJDFQBFDG-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-methyl-1-(N-piperidino)-1,3-butadiene 在 盐酸 、 氢氧化钾 作用下， 以 苯 为溶剂， 反应 241.0h， 生成 ethyl 6-(2'-methyl-1'-propenyl)-4-methyl-1,3-cyclohexadienecarboxylate
  参考文献：
  名称：

  Mechanism of cyclocondensation of isoprenoid acyclic ?,?-enals with monoethyl malonate under the conditions of the Knoevenagel reaction

  摘要：

  It was shown that the formation of the di- and trisubstituted derivatives of 1.3-cyclohexadiene-1-carboxylic acid during the condensation of 3-methyl-2-butenal, citral, and farnesal with monoethyl malonate in the presence of secondary amines takes place through the enamines corresponding to these aldehydes, which add to the monoesters of the respective alkenylidenemalonic acids (the "normal" products of the Knoevenagel reaction) by a mechanism of [4 + 2]-cycloaddition. The free carboxyl group in the dienophile is required for the spontaneous transformation of the intermediate [4 + 2]-cycloadducts into the derivatives of cyclohexadiene-1-carboxylic acid in which the catalyst of the process (the secondary amine) is regenerated.

  DOI：

  10.1007/bf00961358
• 作为产物：
  描述：

  哌啶 、 3-甲基-2-丁烯醛 以57%的产率得到3-methyl-1-(N-piperidino)-1,3-butadiene
  参考文献：
  名称：

  Mechanism of cyclocondensation of isoprenoid acyclic ?,?-enals with monoethyl malonate under the conditions of the Knoevenagel reaction

  摘要：

  It was shown that the formation of the di- and trisubstituted derivatives of 1.3-cyclohexadiene-1-carboxylic acid during the condensation of 3-methyl-2-butenal, citral, and farnesal with monoethyl malonate in the presence of secondary amines takes place through the enamines corresponding to these aldehydes, which add to the monoesters of the respective alkenylidenemalonic acids (the "normal" products of the Knoevenagel reaction) by a mechanism of [4 + 2]-cycloaddition. The free carboxyl group in the dienophile is required for the spontaneous transformation of the intermediate [4 + 2]-cycloadducts into the derivatives of cyclohexadiene-1-carboxylic acid in which the catalyst of the process (the secondary amine) is regenerated.

  DOI：

  10.1007/bf00961358

文献信息

• NIGMATOV, A. G.;SEREBRYAKOV, EH. P., IZV. AN CCCP. CEP. XIM.,(1991) N, S. 1089-1100
  作者：NIGMATOV, A. G.、SEREBRYAKOV, EH. P.

  DOI：——

  日期：——
• Acyclic isoprenoid 1,3-dieneamines in the Diels-Alder reaction
  作者：A. G. Nigmatov、�. P. Serebryakov

  DOI：10.1007/bf00961359

  日期：1991.5

  The dieneamines obtained from 3-methyl-2-butenal and citral (Ia) and (Ib, c) enter into [4 + 2]-cycloaddition with monoethyl citrylidenemalonate (II) and prenylidenemalonate (III), respectively, forming the esters of substituted 1,3-cyclohexadiene-1-carboxylic acids with side chains of the isoprenoid type. The same or analogous cyclohexadiene can be obtained from "citral dieneamine" (Ib, c) and typical dienophiles (methyl acrylate, diethyl fumarate, etc.) in a two-stage path, including the initial production of derivatives of 2-amino-3-cyclohexene-1-carboxylic acid in the Diels-Alder reaction and then elimination of the amino group from the cyclic adducts. The isomeric composition of the mixture of cyclic adducts formed in the reaction of (Ib + Ic) with diethyl fumarate under strictly aprotic conditions correlates with the ratio of the structural isomers with a DELTA-3 and DELTA-3(9) bond (Ib, c) in the "citral dieneamine." In the reaction of the dieneamine with the less reactive methyl acrylate the obtained mixture of cyclic adducts contains a significantly larger fraction of the isomer corresponding to the minor DELTA-3(9) isomer of the dieneamine.