1,7,8-triaza-6,6-dimethyl-3,3-diphenyl-5-oxa-2-oxo-1-(p-bromophenyl)spiro[3,4]oct-7-ene | 896746-03-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,7,8-triaza-6,6-dimethyl-3,3-diphenyl-5-oxa-2-oxo-1-(p-bromophenyl)spiro[3,4]oct-7-ene
• 英文别名: 1-(4-Bromophenyl)-6,6-dimethyl-3,3-diphenyl-5-oxa-1,7,8-triazaspiro[3.4]oct-7-en-2-one
• CAS: 896746-03-5
• 化学式: C₂₄H₂₀BrN₃O₂
• 分子量: 462.346
• InChiKey: KCAISPPVGSOWMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  54.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,7,8-triaza-6,6-dimethyl-3,3-diphenyl-5-oxa-2-oxo-1-(p-bromophenyl)spiro[3,4]oct-7-ene 、 4-甲氧基异氰酸苄酯 以 1,4-二氧六环 为溶剂， 以60%的产率得到4-cyano-3,3-diphenyl-1-(p-bromophenyl)-4-(p-methoxybenzyl)-β-lactam
  参考文献：
  名称：

  Reaction of β-lactam carbenes with alkyl isonitriles for a ready approach to 4-cyano and 4-carbamoyl substituted β-lactams

  摘要：

  The reaction of beta-lactam carbenes with alkyl isonitriles was investigated. Two different types of products, 4-cyano- or 4-carbamoyl-beta-lactams, were isolated, depending upon the nature of the alkyl group of the isonitriles. The cyano-beta-lactams were derived by a N-to-C 1,3-rearrangement of the ketenimine intermediates, while the carbamoyl-beta-lactams were the hydrolysis products of the intermediates. This work extends the application of beta-lactam carbenes, and provides a very simple and efficient route to 4-cyano- or 4-carbamoyl-beta-lactams, which are versatile synthetic intermediates and new chemical entities of potential biological activity. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.111
• 作为产物：
  描述：

  二苯基乙酰氯 、 (4-bromo-phenyl)-(5,5-dimethyl-5H-[1,3,4]oxadiazol-2-ylidene)-amine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以95%的产率得到1,7,8-triaza-6,6-dimethyl-3,3-diphenyl-5-oxa-2-oxo-1-(p-bromophenyl)spiro[3,4]oct-7-ene
  参考文献：
  名称：

  High Nucleophilicity of Cyclic Amidocarbene toward Aryl Isocyanates, New Approach to Spiro[azetidinone-4,3‘-indolinone] Derivatives

  摘要：

  The nucleophilic addition of beta-lactam-4-ylidenes 2, a type of ambiphilic cyclic amidocarbene, to aryl isocyanates has been studied and their application in organic synthesis has been demonstrated. Thermolysis of spiro[beta-lactam-4,2'-oxadiazolines] 1 in the presence of aryl isocyanates afforded both N-lactam and O-lactam substituted spiro[azetidine-2-one-4,3'-indole-2'-one] derivatives 5 and 6 in the total yield of 65-86%. Upon hydrolysis, products 5 and 6 were converted into spiro[azetidine-2-one-4,3'-indole-2'-one] 9 that was analogous to known biologically active compounds.

  DOI：

  10.1021/jo060265h

文献信息

• Interaction of β-Lactam Carbenes with Aryl Isonitriles:  An Unprecedented Rearrangement of 2-Azetidinonylidene Indoles to δ-Carbolinones
  作者：Ying Cheng、Lan-Qing Cheng

  DOI：10.1021/jo0700631

  日期：2007.3.1

  The reaction of, beta-lactam carbenes with aryl isonitriles proceeded in a novel [2 + 2] fashion to give high yields of 2-azetidinonylidene indoles 4, which underwent an unprecedented rearrangement to furnish 4-arylimino-delta-carbolin-2-ones 5 in almost quantitative yields. Acid catalyzed rearrangement and the subsequent hydrolysis of 2-azetidinonylidene indoles 4 produced two types of delta-carbolin-2,4-diones 10 and 11, respectively, in good to excellent yields. The photophysical study showed that both delta-carbolin-2,4-diones 10 and 11 are highly fluorescent with the fluorescent quantum yields being up to 0.43.