1-vinyl-4,5-dihydihydrobenz[g]indole | 84443-05-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-vinyl-4,5-dihydihydrobenz[g]indole
• 英文别名: 1-vinyl-4,5-dihydrobenzo[g]indole；N-vinyl-4,5-dihydrobenzo[g]indole；1-ethenyl-4,5-dihydrobenzo[g]indole
• CAS: 84443-05-0
• 化学式: C₁₄H₁₃N
• 分子量: 195.264
• InChiKey: HIGGXPGXVMEOSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-vinyl-4,5-dihydihydrobenz[g]indole 、 N,N-二甲基甲酰胺 在 草酰氯 、 水 、 sodium acetate 作用下， 以 二氯甲烷 为溶剂， 反应 1.17h， 以89%的产率得到1-vinyl-4,5-dihydrobenzo[g]indole-2-carbaldehyde
  参考文献：
  名称：

  1-乙烯基吡咯-2-甲醛的有效途径

  摘要：

  通过N，N-二甲基甲酰胺/草酰氯试剂系统（CH 2 Cl 2，室温，40分钟）使1-乙烯基吡咯甲酰基化，以产生高达97％的产率的相应的1-乙烯基吡咯-2-甲醛。 醛-吡咯-甲酰化-草酰氯-Vilsmeier-Haack反应

  DOI：

  10.1055/s-0028-1083312
• 作为产物：
  描述：

  4,5-dihydrobenzo[g]indole 、 乙炔 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 120.0 ℃ 、98.06 kPa 条件下， 反应 8.0h， 以97%的产率得到1-vinyl-4,5-dihydihydrobenz[g]indole
  参考文献：
  名称：

  New examples of the vinylation of NH-heterocycles with acetylene at atmospheric pressure in the KOH-DMSO system

  摘要：

  DOI：

  10.1007/bf00542777

文献信息

• Unusual Lewis-acid catalyzed formal (3+3)-cycloaddition of azomethine imines and nitrones to N-vinylpyrroles
  作者：Mariia M. Efremova、Rafael R. Kostikov、Alexander V. Stepakov、Taras L. Panikorovsky、Victoriya S. Shcherbakova、Andrey V. Ivanov、Alexander P. Molchanov

  DOI：10.1016/j.tet.2016.12.034

  日期：2017.2

  The addition of Lewis acids change the reaction mechanism of the cycloaddition of N-vinylpyrroles with azomethine imine and C,N-diarylnitrones. The formal (3+3)-cycloaddition is observed instead of (3+2)-dipolar cycloaddition, which take place in the absence of catalysts. This unusual (3+3)-cycloaddition leads to heterocyclic compounds with pyrazolo[1,2-a]pyrrolo[1,2-d][1,2,4]triazine- and pyrrolo[2

  路易斯酸的加入改变了N-乙烯基吡咯与偶氮甲亚胺和C，N-二芳基硝酮的环加成反应的机理。观察到形式的（3 + 3）-环加成反应，而不是在没有催化剂的情况下发生的（3 + 2）-偶极环加成反应。这种不寻常的（3 + 3）-环加成反应会生成带有吡唑并[1,2- a ]吡咯并[1,2- d ] [1,2,4]三嗪-和吡咯并[2,1- d ] [1的杂环化合物，2,5]恶二嗪核，其很难通过其他方法获得。
• The (3+2)- and formal (3+3)-cycloadditions of N-vinylpyrroles with cyclic nitrones and C,N-cyclic azomethine imines
  作者：Kseniia K. Afanaseva、Mariia M. Efremova、Svetlana V. Kuznetsova、Andrey V. Ivanov、Galina L. Starova、Alexander P. Molchanov

  DOI：10.1016/j.tet.2018.07.040

  日期：2018.9

  N-vinylpyrroles with 3,4-dihydroisoquinoline-N-oxides: formal (3 + 3)-cycloaddition proceeds instead of (3 + 2)-cycloaddition. In the case of benzoyl(3,4-dihydroisoquinolin-2-ium-2-yl)amides, reaction path does not change in the same conditions, but changing of the diastereoselectivity occurs and other diastereomer of (3 + 2)-cycloaddition became predominant.

  路易斯酸的添加改变了N-乙烯基吡咯与3，4-二氢异喹啉-N-氧化物的反应路径：进行了正式的（3 + 3）-环加成而不是（3 + 2）-环加成。在苯甲酰基（3,4-二氢异喹啉-2-基-2-基）酰胺的情况下，反应路径在相同条件下不变，但是发生非对映选择性的变化，并且其他（3 + 2）-环加成的非对映异构体变为占主导地位。
• The “one pot” synthesis of 4,5-dihydrobenzo[g]indole and its 1-vinyl derivative from 1-tetralone, hydroxylamine, and dichloroethane in the system KOH-DMSO
  作者：A. V. Ivanov、V. S. Barnakova、A. I. Mikhaleva、B. A. Trofimov

  DOI：10.1007/s11172-013-0372-y

  日期：2013.11

  4,5-Dihydrobenzo[g]indole and its 1-vinyl derivative were obtained from 1-tetralone, hydroxylamine, and dichloroethane in the superbasic system KOH-DMSO (140 °C, 3 h) in a total yield of 88%. The proposed method provides a fire-safe and explosion-proof approach to indole derivatives in demand.

  4,5-二氢苯并[g]吲哚及其1-乙烯基衍生物由1-四氢萘酮、羟胺和二氯乙烷在超碱性体系KOH-DMSO（140 °C，3 h）中制备，总收率为88%。该方法为吲哚衍生物的制备提供了一种防火防爆的方法。
• 4,4-Difluoro-4-bora-3a,4a-diaza-<i>s</i>-indacene (BODIPY) Dyes Modified for Extended Conjugation and Restricted Bond Rotations
  作者：Jiong Chen、Armin Burghart、Agnes Derecskei-Kovacs、Kevin Burgess

  DOI：10.1021/jo991927o

  日期：2000.5.1

  Five new, constrained, aryl-substituted 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes (3f,g and 4h-j) were prepared and investigated to see if they have more favorable fluorescence characteristics than the unconstrained systems 2 that were prepared in previous studies. Dye types 3 and 4 have relatively rigid conformations caused by the heteroatom (3f and 3g) or ethylene bridge (4h-j) linkers that preclude free rotation of the substituted-benzene molecular fragments. In the event, the new dye types 3 and 4 have longer lambda(max) (abs) (620-660 nm) and lambda(max) (fluor) (630-680 nm) values than compounds 2, They also exhibit higher extinction coefficients (>100 000 M (1) cm(-1) except for 3g). Their fluorescent quantum yields are high (up to 0.72 for 4j), with the exception of compound 3g, which has a quantum yield of only 0.05. The redox properties of dyes 3 and 4 have also been examined.
• Selective synthesis of 1-vinylpyrroles directly from ketones and acetylene: Modification of trofimov reaction
  作者：A. I. Mikhaleva、E. Yu. Shmidt、A. V. Ivanov、A. M. Vasil’tsov、E. Yu. Senotrusova、N. I. Protsuk

  DOI：10.1134/s1070428007020133

  日期：2007.2

  Consecutive treatment of ketones with a system NH2OH center dot HCl-NaHCO3-DMSO and acetylene excess in the presence of KOH (100-120 degrees C, initial acetylene pressure 12-15 at) led to a selective formation of 2- and 2,3-substituted 1-vinylpyrroles in 51-79% yields. Ketones of aliphatic, cycloaliphatic, aromatic, heteroaromatic, and tetrahydronaphthalene series were involved into the reaction.