| 1637412-20-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1637412-20-4
• 化学式: C₁₉H₁₆BrNO
• 分子量: 354.246
• InChiKey: WFQRRPXCQHJISP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  在 copper diacetate 、 1-叠氮基-1,2-苯并氧代-3(1h)-酮 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以86%的产率得到9b-azido-1-(3-bromophenyl)-3a,5-dimethyl-5,9b-dihydro-3H-pyrrolo[3,4-c]quinolin-4(3aH)one
  参考文献：
  名称：

  Copper-Catalyzed Radical [2 + 2 + 1] Annulation of Benzene-Linked 1,n-Enynes with Azide: Fused Pyrroline Compounds

  摘要：

  A novel selective copper-catalyzed radical [2 + 2 + 1] annulation of benzene-linked 1,n-enynes with azido-benziodoxolone to access fused pyrroline compounds, including 3H-pyrrolo[3,4-c]quinolin-4(3aH)-ones, chromeno[3,4-c]pyrrol-4(9bH)-one, and indeno[1,2-c]pyrroline, has been developed, which proceeds via the addition of the azide radical to the alkene, annualtion, and azidation cascade.

  DOI：

  10.1021/acs.orglett.5b03040

文献信息

• Photocatalytic Decarboxylative [2 + 2 + <i>m</i>] Cyclization of 1,7-Enynes Mediated by Tricyclohexylphosphine and Potassium Iodide
  作者：Hui-Yuan Liu、Yuan Lu、Yang Li、Jin-Heng Li

  DOI：10.1021/acs.orglett.0c03182

  日期：2020.11.20

  photocatalytic decarboxylative [2 + 2 + m] cyclization of 1,7-enynes with alkyl N-hydroxyphthalimide (NHP) esters, using tricyclohexylphosphine and potassium iodide as redox catalysts, is reported for the construction of functional polycyclic compounds. This protocol tolerates primary, secondary, and tertiary alkyl NHP esters through a single reaction via decarbonylation, radical addition, C–H functionalization

  据报道，使用三环己基膦和碘化钾作为氧化还原催化剂，用烷基N-羟基邻苯二甲酰亚胺（NHP）酯进行的1,7-烯炔的新型光催化脱羧[2 + 2 + m ]环化反应。该方案通过脱羰，自由基加成，CH-H官能化和在温和条件下环化的单一反应，可以耐受伯，仲和叔烷基NHP酯。
• Sulfur Incorporation Using Disulfanes as the Sulfur Atom Source Enabled Metal‐Free Heteroannulation of 1,7‐Enynes
  作者：Jing‐Hao Qin、Jiang‐Xi Yu、Jin‐Heng Li、De‐Lie An

  DOI：10.1002/adsc.201900621

  日期：2019.9.3

  A new oxidative [2+2+1] heteroannulation of 1,7‐enynes with disulfanes promoted by Et3N, producing 3,3a‐dihydro‐thieno[3,4‐c]quinolin‐4(5H)‐ones, is described. This reaction is achieved by using equivalent amounts of 1,7‐enynes, sulfur atoms (disulfanes), tert‐butyl peroxybenzoate (TBPB) as an oxidant and Et3N as the base, and represents an unprecedented strategy to applications of disulfanes as sulfur

  一种新的氧化[2 + 2 + 1]的1,7-烯炔与促进的Et disulfanes杂环化3 N，产生3,3-一个二氢-噻吩并[3,4-c]喹啉-4（5 ħ） -酮进行说明。通过使用等量的1,7-炔，硫原子（二硫烷），过氧苯甲酸叔丁酯（TBPB）作为氧化剂和Et 3 N作为碱来实现该反应，这是将二硫代硫磺应用的空前策略合成中的原子源。
• Cascade Nitration/Cyclization of 1,7-Enynes with<i>t</i>BuONO and H₂O: One-Pot Self-Assembly of Pyrrolo[4,3,2-<i>de</i>]quinolinones
  作者：Yu Liu、Jia-Ling Zhang、Ren-Jie Song、Peng-Cheng Qian、Jin-Heng Li

  DOI：10.1002/anie.201404192

  日期：2014.8.18

  Here we describe the one‐pot construction of the pyrrolo[4,3,2‐de]quinolinone scaffold by a cascade nitration/cyclization sequence of 1,7‐enynes with tBuONO and H2O. The cascade proceeds through alkene nitration, 1,7‐enyne 6‐exo‐trig cyclization, CH nitrations, and redox cyclization, and exhibits excellent functional group tolerance. The mechanism was investigated using in situ high‐resolution mass

  在这里，我们描述了1,7-烯炔与t BuONO和H 2 O的级联硝化/环化序列的吡咯并[4,3,2-de]喹啉酮骨架的一锅构建。级联通过烯烃硝化进行， 1,7-烯炔-6-外型-trig环化，C  ħ硝化，和氧化还原环合，并表现出优异的官能团耐受性。使用原位高分辨率质谱（HR-MS）研究了该机理。
• Intermolecular oxidative decarbonylative [2 + 2 + 2] carbocyclization of N-(2-ethynylaryl)acrylamides with tertiary and secondary alkyl aldehydes involving C(sp³)–H functionalization
  作者：Yang Li、Gao-Hui Pan、Ming Hu、Bang Liu、Ren-Jie Song、Jin-Heng Li

  DOI：10.1039/c6sc02451c

  日期：——

  s with tertiary and secondary alkyl aldehydes is described. This reaction enables the formation of three new C–C bonds in a single reaction by a sequence of oxidative decarbonylation, radical addition across C–C unsaturated bonds, C–H functionalization and annulation, and represents the first oxidative decarbonylative [2 + 2 + 2] carbocyclization approach using tertiary and secondary alkyl aldehydes

  描述了N- (2-乙炔芳基)丙烯酰胺与叔和仲烷基醛的新型无金属氧化脱羰[2 + 2 + 2]碳环化反应。该反应通过一系列氧化脱羰、C-C不饱和键上的自由基加成、C-H官能化和环化，能够在一个反应​​中形成三个新的C-C键，并且代表了第一个氧化脱羰[2 + 2 + 2]使用叔烷基醛和仲烷基醛作为双碳单元来组装六元碳环稠合多环的碳环化方法。
• Visible-Light-Promoted Tandem Annulation of <i>N</i>-(<i>o</i>-Ethynylaryl)acrylamides with CH₂Cl₂
  作者：Yu Liu、Ren-Jie Song、Shenglian Luo、Jin-Heng Li

  DOI：10.1021/acs.orglett.7b03561

  日期：2018.1.5

  A novel tandem annulation of N-(o-ethynylaryl)acrylamides, with CH2Cl2 as a one-carbon unit, for the divergent synthesis of cyclopenta[c]quinolin-4(5H)-ones and benzo[j]phenanthridin-6(5H)-ones, which relies on the substitution effect of the 2 position of the acrylamide moiety, is described. Promoted by the visible-light photoredox catalysis, this reaction allows the formation of multiple chemical

  以CH 2 Cl 2为一个碳原子单元的N-（邻乙炔基芳基）丙烯酰胺的新型串联环化反应，用于发散合成环戊[ c ]喹啉4（5H）-酮和苯并[ j ]菲啶-描述了依赖于丙烯酰胺部分的2位的取代作用的6（5H）-1。在可见光氧化还原催化的促进下，该反应允许通过多个C–Cl / CH–H功能化和[2 + 2 +1]级联反应形成多个化学键。