1,2-di[(indol-1-yl)methyl]benzene | 464916-31-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1,2-di[(indol-1-yl)methyl]benzene
• 英文别名: 1-[[2-(Indol-1-ylmethyl)phenyl]methyl]indole
• CAS: 464916-31-2
• 化学式: C₂₄H₂₀N₂
• 分子量: 336.436
• InChiKey: VCWBEHRIKPJGOI-UHFFFAOYSA-N

物化性质

• 熔点：
  168-170 °C
• 沸点：
  573.7±43.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  9.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-allyl-3-diazoindolin-2-one 、 1,2-di[(indol-1-yl)methyl]benzene 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以95%的产率得到1,2-bis[((1'-allyl-1',3'-dihydro-1H-[3,3']biindolyl-2'-on)-1-yl)methyl]benzene
  参考文献：
  名称：

  Rhodium(II) catalyzed intermolecular double C-alkylation: a method for the synthesis of tetraindoles and indolophanes

  摘要：

  Double C-alkylation of cyclic diazoamides or bis-diazoamides with indoles or bis-indoles has been achieved to synthesize tetraindole derivatives using rhodium(II) acetate as a catalyst under mild reaction conditions with complete regioselectivity. The intermolecular double C-alkylation reaction strategy was successfully applied to synthesize indolophanes in moderate yield with excellent regiocontrol. The structure and stereochemistry of macrocycles were unequivocally confirmed with the help of single-crystal X-ray structure analyses. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.073
• 作为产物：
  描述：

  吲哚啉-2-羧酸 、 邻苯二甲醛 在 苯甲酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 36.1h， 以51%的产率得到1,2-di[(indol-1-yl)methyl]benzene
  参考文献：
  名称：

  布朗斯台德酸催化的脱羧氧化还原胺化：通过异构化反应从亚甲亚胺叶立德形成N-烷基炔

  摘要：

  描述了涉及醛与2-羧基二氢吲哚的布朗斯台德酸催化的脱羧氧化还原胺化反应，用于合成N-烷基吲哚。醛与2-羧基二氢吲哚的脱羧缩合反应原位产生偶氮甲亚胺，然后通过异构化反应转化为N-烷基吲哚。

  DOI：

  10.1021/jo102218v

文献信息

• Synthesis and solid state structures of N,N′-linked carbazoles and indoles
  作者：Jason Bloxham、Christopher J Moody、Alexandra M.Z Slawin

  DOI：10.1016/s0040-4020(02)00344-7

  日期：2002.5

  The synthesis and solid state conformations of a number of N,N′-linked carbazoles and indoles has been investigated. Using xylyl-based linkers, the o, m and p-linked carbazoles and indoles 4–6, 8–10 and 12, 13 were prepared. Likewise, unsymmetrical derivatives were also prepared. Investigation using X-ray crystallography showed that the heterocycles adopted either stretched or folded conformations

  已经研究了许多N，N′-连接的咔唑和吲哚的合成和固态构象。使用基于二甲苯基的接头，所述Ó，米和p -连接的咔唑和吲哚4 - 6，8 - 10和12，13制备。同样，还制备了不对称衍生物。使用X射线晶体学的研究表明，杂环在固态时采用了拉伸或折叠构象。
• Methanal Extrusion in ipso-Substitution Reactions of Hydroxymethylindoles
  作者：Jeremy C. Dobrowolski、Kittiya Somphol、Mardi Santoso、Hung Duong、Christopher R. Gardner、Naresh Kumar、David StC. Black

  DOI：10.1071/ch17257

  日期：——

  A range of 3-hydroxymethylindoles undergo acid-catalysed reactions involving ipso-electrophilic substitution with the extrusion of methanal and the formation of diindolylmethane moieties. Both inter- and intramolecular processes lead to macrocyclic compounds 10 and 14.

  的3-hydroxymethylindoles一系列经历涉及酸催化的反应本位与甲醛的挤出和吲哚基甲烷基团的形成-electrophilic取代。分子间和分子内过程均导致大环化合物10和14。
• Regioselective synthesis of mono- and bis-decahydrobenzocarbazoles via tandem reactions of α-diazo ketones
  作者：Sengodagounder Muthusamy、Chidambaram Gunanathan、Eringathodi Suresh

  DOI：10.1016/j.tet.2004.06.053

  日期：2004.8

  Regioselective intermolecular 1,3-dipolar cycloaddition reactions of rhodium generated carbonyl ylides with indoles are reported in this paper. Intermolecular 1,3-dipolar cycloaddition reactions of five-membered-ring cyclic carbonyl ylides with indole and substituted indoles afforded hexahydro-2H-carbazol-2-ones in a regioselective manner. Similarly, reactions of cyclic carbonyl ylides were carried

  本文报道了铑生成的羰基化物与吲哚的区域选择性分子间1,3-偶极环加成反应。五元环环状羰基羰基化物与吲哚和取代的吲哚的分子间1,3-偶极环加成反应以区域选择性方式提供了六氢-2 H-咔唑-2-酮。类似地，进行环状羰基酰基化物的反应以提供具有高区域选择性的十氢苯并[ c ]咔唑或十氢环戊[ c ]咔唑。有趣的是，其他可能的区域异构体十氢苯并[ a]通过环羰基羰基化合物和具有吸电子取代基的吲哚反应也可以得到]咔唑。区域异构体6,11c-环氧-1,2,3,4,4a，5,6,6a，11b，11c-十氢-4a-甲基-5-氧代-7 H-苯并[ c ]咔唑的结构和立体化学和11-苯磺酰基-6,11b-环氧-2,3,4,4a，5,6,6a，11,11a，11b-十氢-4a-甲基-5-氧代-1 H-苯并[ a]单晶X射线分析明确证实了]咔唑。为了推进该研究，首次证明了具有不同芳基和烷基间隔基的双吲哚的五元环环
• Synthesis of Some (Triindolyl)dimethanes and (Tetraindolyl)trimethanes
  作者：David StC. Black、Kittya Somphol、Naresh Kumar

  DOI：10.3987/com-20-14397

  日期：——
• Reactions of macrocyclic rhodium carbenoids: regioselective synthesis of indol-3-yl macrocyclic lactones and cryptands
  作者：Sengodagounder Muthusamy、Boopathy Gnanaprakasam

  DOI：10.1016/j.tetlet.2007.11.102

  日期：2008.1

  A wide variety of new macrocyclic diazocarbonyl compounds with various spacers was synthesized. Macrocyclic rhodium(H) carberioid insertion with various substituted indoles was performed to afford regioselectively, indol-3-yl macrocyclic di- or tetralactones (C3-alkylation). Double carberioid insertion was also performed to afford indolyl cryptand molecules. (C) 2007 Elsevier Ltd. All rights reserved.