7,8-dihydro-5H-benzo[4,5]azepino[2,1-a]isoindol-5-one | 71898-40-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 7,8-dihydro-5H-benzo[4,5]azepino[2,1-a]isoindol-5-one
• 英文别名: 7,8-Dihydroisoindolo[2,3-c][3]benzazepin-5-one
• CAS: 71898-40-3
• 化学式: C₁₇H₁₃NO
• 分子量: 247.296
• InChiKey: KBOZFCMYUJLJDD-UHFFFAOYSA-N

物化性质

• 熔点：
  128-129 °C
• 沸点：
  473.2±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7,8-dihydro-5H-benzo[4,5]azepino[2,1-a]isoindol-5-one 生成 13-Bromo-13a-methoxy-7,8,13,13a-tetrahydro-benzo[4,5]azepino[2,1-a]isoindol-5-one
  参考文献：
  名称：

  SCARTONI V.; FIASCHI R.; CATALANO S.; MORELLI I.; MARSILI A., J. CHEM. SOC. PERKIN TRANS., PART 1, 1979, NO 6, 1547-1551

  摘要：

  DOI：
• 作为产物：
  描述：

  2-碘苯乙胺 在 palladium diacetate 、 potassium carbonate 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 7,8-dihydro-5H-benzo[4,5]azepino[2,1-a]isoindol-5-one
  参考文献：
  名称：

  Intramolecular Heck reaction of methylenephthalimidine derivatives: a simple route to lennoxamine and chilenine

  摘要：

  A new concise route to the key intermediate for isoindolobenazepine alkaloids, lennoxamine and chilenine, was developed using amine and keto-ester condensation followed by Heck reaction. (C) 2003 Elsevier Ltd. All riellts reserved.

  DOI：

  10.1016/j.tetlet.2003.09.069

文献信息

• Electroreductive Intramolecular Coupling of Phthalimides with Aromatic Aldehydes: Application to the Synthesis of Lennoxamine
  作者：Naoki Kise、Shinsaku Isemoto、Toshihiko Sakurai

  DOI：10.1021/jo2018735

  日期：2011.12.2

  The electroreductive intramolecular coupling of phthalimides with aromatic aldehydes in the presence of chlorotrimethylsilane and triethylamine led to five-, six-, and seven-membered cyclized products (58–84%). The electroreductive cyclization was applied to the total synthesis of lennoxamine.

  在氯代三甲基硅烷和三乙胺的存在下，邻苯二甲酰亚胺与芳族醛的电还原分子内偶联产生五元，六元和七元环化产物（58-84％）。电还原环化被用于伦诺明的全合成。
• Intramolecular Arylation of Tertiary Enamides through Pd(OAc)₂-Catalyzed Dehydrogenative Cross-Coupling Reaction: Construction of Fused <i>N</i>-Heterocyclic Scaffolds and Synthesis of Isoindolobenzazepine Alkaloids
  作者：Wenju Zhu、Shuo Tong、Jieping Zhu、Mei-Xiang Wang

  DOI：10.1021/acs.joc.9b00010

  日期：2019.3.1

  Pd(OAc)2-catalyzed intramolecular dehydrogenative cross-coupling reaction between tertiary enamides, which were derived from the condensation of 2-arylethylamines and methyl o-acetylbenzoate, and arenes enabled synthesis of 7,8-dihydro-5H-benzo[4,5]azepino[2,1-a]isoindol-5-one derivatives under mild conditions. The synthetic method was applied in the total synthesis of aporhoeadane alkaloids palmanine

  Pd（OAc）2催化叔烯酰胺之间的分子内脱氢交叉偶联反应，后者是由2-芳基乙胺与邻乙酰基苯甲酸甲酯的缩合反应生成的，而芳烃则可以合成7,8-二氢-5 H-苯并[4] ，5] azepino [2,1 - a ] isoindol-5-one衍生物在温和的条件下。该合成方法仅需三到四个步骤即可用于阿魏酸钠，生物碱棕榈碱，伦诺沙明和邻苯二胺的全合成。
• Synthesis of fused rings at a pivotal nitrogen: tandem Heck reactions of N-vinyl-2-iodobenzamides
  作者：Alberto Garcı́a、David Rodrı́guez、Luis Castedo、Carlos Saá、Domingo Domı́nguez

  DOI：10.1016/s0040-4039(01)00077-6

  日期：2001.3

  A short two-step synthesis of the tetracyclic nitrogen heterocycles 2 (isoindoloneindole, isoindoloneisoquinoline and isoindolone[3]benzazepine) is presented. Condensation of the corresponding o-bromoarylamine with acetaldehyde followed by acylation with o-iodobenzoyl chloride affords the key dihalo N-vinylbenzamides 1, which are then cyclized by a tandem Heck reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.