methyl 2-[(E)-(4-methoxyphenyl)methylidene]aminobutanoate | 113370-79-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-[(E)-(4-methoxyphenyl)methylidene]aminobutanoate
• 英文别名: methyl N-p-methoxybenzylidene(methyl)alaninate
• CAS: 113370-79-9
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: LVBTUZPXLYFFHI-NTEUORMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  47.89
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 2-[(E)-(4-methoxyphenyl)methylidene]aminobutanoate 在 18-冠醚-6 、 盐酸羟胺 、 potassium tert-butylate 、 碳酸氢钠 、 sodium carbonate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 水 、 乙酸乙酯 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 13.17h， 生成 methyl 2-ethyl-2-[hydroxy(mesitylacetyl)amino]butanoate
  参考文献：
  名称：

  Synthesis and insecticidal activity of novel N-oxydihydropyrroles: 4-hydroxy-3-mesityl-1-methoxymethoxy derivatives with various substituents at the 5-position

  摘要：

  This paper reports the synthesis and insecticidal activity of a series of novel 4-hydroxy-3-mesityl-1-methoxymethoxy-1,5-dihydro-2H-pyrrol-2-one derivatives, in which the substituents at the 5-position were varied with a number of alkyl and spirocycloalkyl groups. Investigation of the structure-activity relationships revealed that small alkyl and spirocyclohexyl groups had a favorable effect on the insecticidal activity of these agents against Myzus persicae. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00474-1
• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 DL-2-氨基丁酸甲酯盐酸盐 在 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以86.2%的产率得到methyl 2-[(E)-(4-methoxyphenyl)methylidene]aminobutanoate
  参考文献：
  名称：

  Synthesis and insecticidal activity of novel N-oxydihydropyrroles: 4-hydroxy-3-mesityl-1-methoxymethoxy derivatives with various substituents at the 5-position

  摘要：

  This paper reports the synthesis and insecticidal activity of a series of novel 4-hydroxy-3-mesityl-1-methoxymethoxy-1,5-dihydro-2H-pyrrol-2-one derivatives, in which the substituents at the 5-position were varied with a number of alkyl and spirocycloalkyl groups. Investigation of the structure-activity relationships revealed that small alkyl and spirocyclohexyl groups had a favorable effect on the insecticidal activity of these agents against Myzus persicae. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00474-1

文献信息

• XY–ZH Systems as potential 1,3-dipoles. Part 8. Pyrrolidines and Δ⁵-pyrrolines (3,7-diazabicyclo[3.3.0]octenes) from the reaction of imines of α-amino acids and their esters with cyclic dipolarophiles. Mechanism of racemisation of α-amino acids and their esters in the presence of aldehydes
  作者：Kitti Amornraksa、Ronald Grigg、H. Q. Nimal Gunaratne、James Kemp、Visuvanathar Sridharan

  DOI：10.1039/p19870002285

  日期：——

  Imines of α-amino acid esters with aromatic, heterocyclic, and aliphatic aldehydes generate azomethine ylides stereospecifically by a prototropic shift on heating in toluene. The azomethine ylides undergo cycloaddition to N-phenylmaleimide, maleic anhydride, and p-naphthoquinone via an endo-transition state to give racemic, single diastereoisomeric, cycloadducts. α-Amino acids undergo analogous cycloadditions

  α-氨基酸酯的亚胺与芳族，杂环和脂族醛一起，通过在甲苯中加热时发生质变，立体定向生成偶氮甲碱。甲亚胺叶立德进行环加成到Ñ苯基马来，马来酸酐，和p -naphthoquinone经由一个内切-过渡状态，得到外消旋的，非对映异构单，cycloadducts。α-氨基酸在热乙酸中经历类似的环加成而不脱羧。讨论了在醛存在下α-氨基酸及其酯的外消旋作用机理。吡咯烷cycloadducts（22）平滑地氧化成相应的Δ 5 -pyrrolines（33）通过二氯二氰基对苯醌。