(+/-)-Verbascenine | 87554-71-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: (+/-)-Verbascenine
• 英文别名: verbascenine；13-acetyl-8-phenyl-1-[(E)-3-phenylprop-2-enoyl]-1,5,9,13-tetrazacycloheptadecan-6-one
• CAS: 87554-71-0
• 化学式: C₃₀H₄₀N₄O₃
• 分子量: 504.673
• InChiKey: QWIQBGWKCLURMP-WUKNDPDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  37
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  81.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-Verbascenine 、 alkaline earth salt of/the/ methylsulfuric acid 生成 9,13-Diacetyl-8-phenyl-1-[(E)-(3-phenyl-acryloyl)]-1,5,9,13-tetraaza-cycloheptadecan-6-one
  参考文献：
  名称：

  Verballoscenine, the Z isomer of verbascenine from Verbascum phoeniceum

  摘要：

  The Z isomer (13-acetyl-1-(Z)-cinnamoyl-6-oxo-8-phenyl-1,5,9,13-tetraazacycloheptadecane; verballoscenine) of the 17-membered macrocyclic lactam alkaloid verbascenine was isolated from Verbascum phoeniceum and structurally characterized. The presence in the same plant material of the analogous N-13 non-acetyl alkaloids verbacine and verballocine as precursors in the biogenesis of verbascenine and verballoscenine is reported. Copyright (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0031-9422(96)00623-1
• 作为产物：
  描述：

  3-苯基-2-丙烯酰氯 在 三乙胺 、 3,5-双(三氟甲基)苯硼酸 作用下， 以 二氯甲烷 为溶剂， 生成 (+/-)-Verbascenine
  参考文献：
  名称：

  Antimony-Templated Macrolactamization of Tetraamino Esters. Facile Synthesis of Macrocyclic Spermine Alkaloids, (±)-Buchnerine, (±)-Verbacine, (±)-Verbaskine, and (±)-Verbascenine

  摘要：

  DOI：

  10.1021/ja953541a

文献信息

• β-Lactams as building blocks in the synthesis of macrocyclic spermine and spermidine alkaloids
  作者：Harry H Wasserman、Haruo Matsuyama、Ralph P Robinson

  DOI：10.1016/s0040-4020(02)00731-7

  日期：2002.8

  Syntheses of the macrocyclic spermidine alkaloids (±)-celacinnine (1) and (±)-dihydroperiphylline (2) as well as the related spermine alkaloid (±)-verbascenine (3) were accomplished by means of sequential ring expansions of smaller lactam rings. Three ring expansion methods were employed: (1) transamidation of N-(aminoalkyl)lactams, (2) β-lactam-lactim ether condensation followed by reductive cleavage

  大环亚精胺生物碱（±）-celacinnine（1）和（±）-二氢茶碱（2）以及相关的亚精胺生物碱（±）-verbascenine（3）的合成是通过较小内酰胺环的连续环扩展来完成的。使用了三种扩环方法：（1）N-（氨基烷基）内酰胺的转酰胺基化，（2）β-内酰胺-内酰胺醚缩合，然后用NaBH 3 CN / AcOH还原双环4-氧代四氢嘧啶产物和（3）形成双环酰基肼，然后用Na / NH 3裂解N–N键。每个合成均以4-苯基氮杂环丁烷-2-酮中间体的扩环为特征，该中间体会发生酰胺基扩环或内酰胺醚缩合反应。
• Metal-Templated Macrolactamization of Triamino and Tetramino Esters. Facile Synthesis of Macrocyclic Spermidine and Spermine Alkaloids, (<i>S</i>)-(+)-Dihydroperiphylline, (±)-Buchnerine, (±)-Verbacine, (±)-Verbaskine, and (±)-Verbascenine
  作者：Yoshichika Kuroki、Kazuaki Ishihara、Naoyuki Hanaki、Suguru Ohara、Hisashi Yamamoto

  DOI：10.1246/bcsj.71.1221

  日期：1998.5

  The total synthesis of spermidine and spermine alkaloids, (S)-(+)-dihydroperiphylline (1), (±)-buchnerine (2), (±)-verbacine (3), (±)-verbaskine (4), and (±)-verbascenine (5), is described. The construction of macrocyclic lactams has been efficiently accomplished by the metal-templated cyclization of triamino esters and tetraamino esters. It was also found that the antimony(III) ethoxide is useful

  亚精胺和精胺生物碱、(S)-(+)-dihydroperiphylline (1)、(±)-buchnerine (2)、(±)-verbacine (3)、(±)-verbaskine (4) 和(±)-verbascenine (5)，描述。大环内酰胺的构建已通过三氨基酯和四氨基酯的金属模板环化有效完成。还发现乙氧基锑(III)可用作分子间酰胺化催化剂。
• The synthesis of (±)-verbascenine
  作者：Harry H. Wasserman、Ralph P. Robinson

  DOI：10.1016/s0040-4039(00)88197-6

  日期：1983.1

  A synthesis of (±)-verbascenine is described which includes, as the key step, the coupling of 4-phenylazetidin-2-one with an imino ether derivative of a protected thirteen-membered diamino lactam.

  描述了（±）-麻黄素的合成，其包括作为关键步骤的4-苯基氮杂环丁烷-2-酮与被保护的十三元二氨基内酰胺的亚氨基醚衍生物的偶联。
• Natural preservatives and antimicrobial agents, including compositions thereof
  申请人：Unigen, Inc.

  公开号：US10780173B2

  公开（公告）日：2020-09-22

  Compositions are disclosed herein that comprise a mixture of at least one Albizia extract and a Magnolia extract. In some embodiments, the composition comprises a mixture of at least one Albizia extract enriched for one or more macrocyclic alkaloids and at least one Magnolia extract enrich for one or more lignans.

  本文公开的组合物包括至少一种白花蛇舌草提取物和一种厚朴提取物的混合物。在某些实施方案中，组合物包括至少一种富含一种或多种大环生物碱的白花蛇舌草提取物和至少一种富含一种或多种木脂素的厚朴提取物的混合物。
• Wasserman, Harry H.; Robinson, Ralph P., Heterocycles, 1984, vol. 21, # 1, p. 279 - 288
  作者：Wasserman, Harry H.、Robinson, Ralph P.

  DOI：——

  日期：——