8-bromo-4bH,10H-5-oxa-10a-azabenzo[b]fluoren-11-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 8-bromo-4bH,10H-5-oxa-10a-azabenzo[b]fluoren-11-one
• 英文别名: 8-bromo-4bH-benzo[5,6][1,3]oxazino[2,3-a]isoindol-12(10H)-one；8-Bromo-4b,10-dihydroisoindolo[1,2-b][1,3]benzoxazin-12-one；8-bromo-4b,10-dihydroisoindolo[1,2-b][1,3]benzoxazin-12-one
• 化学式: C₁₅H₁₀BrNO₂
• 分子量: 316.154
• InChiKey: ZQSQRWSGRXZIDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1,3-二氧代异吲哚啉-2-基)甲基乙酯 在 bismuth(lll) trifluoromethanesulfonate 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 8-bromo-4bH,10H-5-oxa-10a-azabenzo[b]fluoren-11-one
  参考文献：
  名称：

  Bi(OTf)3 -通过在串联过程中捕获 Bis-N-Acyliminium 物质催化获得 2,3-取代的异吲哚啉酮和三环 N,O-缩醛

  摘要：

  使用无毒 Bi(OTf)3 催化剂在非常低的负载量 (2 mol-%) 下很容易生成的新 1,3-双-N-酰基铵物种被各种多亲核试剂捕获在分子间和分子内。这种温和、高效、实用和通用的串联方法提供了一系列取代的异吲哚啉酮和环状 N,O-缩醛。

  DOI：

  10.1002/ejoc.201600530

文献信息

• Multimetallic Iridium-Tin (Ir-Sn₃) Catalyst in<i>N</i>-Acyliminium Ion Chemistry: Synthesis of 3-Substituted Isoindolinones<i>via</i>Intra- and Intermolecular Amidoalkylation Reaction
  作者：Arnab Kumar Maity、Sujit Roy

  DOI：10.1002/adsc.201400234

  日期：2014.8.11

  AbstractThe multimetallic iridium‐tritin (Ir‐Sn3) complex [Cp*Ir(SnCl3)2SnCl2(H2O)2}] (1) proved to be a highly effective catalyst towards COH bond activation of γ‐hydroxylactams, leading to a nucleophilic substitution reaction known as the α‐amidoalkylation reaction. Catalyst 1 can be easily synthesized from the reaction of (pentamethylcyclocyclopentadienyl)iridium dichloride dimer [Cp*IrCl2]2} and tin(II) dichloride (SnCl2). In terms of catalyst loading, reaction conditions and yields of the product formed, 1 is found to be superior compared to classical Lewis acid catalysts. Different carbon (arenes, heteroarenes, allyltrimethylsilane, 1,3‐dicarbonyls) and heteroatom (alcohols, thiols, amides and sulfonamides) nucleophiles have been successfully employed in the intramolecular and intermolecular alkylations, as well as in heterocyclization reactions. In the majority of cases good to excellent yields of 3‐substituted isoindolinones and 5‐substituted pyrrolidin‐2‐ones have been obtained. Besides, the reactions are also atom economical and salt free. It is proposed that the multimetallic Ir‐Sn3 catalyst behaves as a mild and selective Lewis acid to activate the γ‐hydroxylactam towards the formation of the N‐acyliminium ion; the latter being trapped by potent nucleophiles leading to the desired products.magnified image