N-benzyl-2-benzylideneacetoacetamide | 88091-10-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-benzyl-2-benzylideneacetoacetamide
• 英文别名: N-benzyl-2-benzylidene-3-oxobutanamide
• CAS: 88091-10-5；88386-34-9；81375-52-2
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: JZTORRSTYWBASZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-2-benzylideneacetoacetamide 在 N-溴代丁二酰亚胺(NBS) 、 对甲苯磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 8.0h， 以80%的产率得到4,4'-(phenylmethylene)bis(5-(benzylamino)furan-3(2H)-one)
  参考文献：
  名称：

  Halonium-Initiated C–O Bond Formation via Umpolung of α-Carbon to the Carbonyl: Efficient Access to 5-Amino-3(2H)-furanones

  摘要：

  Highly efficient C-O bond formation has been developed via carboxylic acid catalyzed reaction of 1-acetylcyclopropanecarboxamides with N-halosuccinimide (NXS), which provides strategically novel and atom-economic access to biologically important 5-amino-3(2H)-furanones. The mechanism of halonium-initiated tandem oxa-cyclization and ring opening of cyclopropane was proposed. A variety of nucleophiles were found to open the cyclopropane.

  DOI：

  10.1021/ol203183k
• 作为产物：
  描述：

  2,2,6-三甲基-4H-1,3-二英-4-酮 、 (E)-N-benzylidene-1-phenylmethanamine 反应 0.5h， 以3%的产率得到N-benzyl-2-benzylideneacetoacetamide
  参考文献：
  名称：

  Sato, Masayuki; Ogasawara, Hiromichi; Yoshizumi, Eriko, Heterocycles, 1982, vol. 17, p. 297 - 300

  摘要：

  DOI：

文献信息

• Synthesis of spiro[isoquinolinone-4,2′-oxiranes] and isoindolinones via a multicomponent reaction of 2-acetyl-oxirane-2-carboxamides, arylaldehydes and malononitrile
  作者：Bing Liu、Enxiang Wei、Shaoxia Lin、Baozhong Zhao、Fushun Liang

  DOI：10.1039/c4cc02141j

  日期：——

  Efficient synthesis of spiro[isoquinolinone-4,2′-oxiranes] was achieved based on a multicomponent one-pot reaction of readily available cis-2-acetyl-oxirane-2-carboxamides, arylaldehydes and malononitrile at room temperature. However, in the reaction with trans-2-acetyl-oxirane-2-carboxamide substrates, 3-iminoisoindolinones were obtained in moderate to high yields.

  基于易得的顺式-2-乙酰基-环氧乙烷-2-甲酰胺、芳基醛和丙二腈在室温下进行的多组分一步反应，实现了螺[异喹啉酮-4,2²-环氧乙烷]的高效合成。然而，在与反式-2-乙酰基-环氧乙烷-2-甲酰胺底物反应时，3-亚氨基异吲哚啉酮的产量适中至较高。
• Masayuki, Sato; Ogasawara, Hiromichi; Yoshizumi, Eriko, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 6, p. 1902 - 1909
  作者：Masayuki, Sato、Ogasawara, Hiromichi、Yoshizumi, Eriko、Kato, Tetsuzo

  DOI：——

  日期：——
• Substrate- and base-dependent reactivities of acylketene toward aryl aldimines derived from 2-amino-4-methylpyridine
  作者：Nuket Ocal、Necla Mor、Ihsan Erden

  DOI：10.1016/j.tetlet.2015.09.157

  日期：2015.11

  Acylketene, generated from 2,2,6-trimethyl-4H-1,3-dioxin-4-one reacts with aryl aldimines derived from 4-methyl-2-aminopyridine to give a variety of products, depending on the substituent on the C-aryl group, base used, and hydrolytic stability of the starting aldimine. Also the presence of the N-(2-pyridyl) group plays an important role in the fate of the reaction course, frequently participating in intramolecular conjugate additions, giving rise to interesting heterocycles. (C) 2015 Elsevier Ltd. All rights reserved.