1,2-bis(1H-indol-2-yl)ethane | 144445-47-6

• 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-bis(1H-indol-2-yl)ethane
• 英文别名: 1,2-bis(2-indolyl)ethane；1,2-bis(1H-2-indolyl)ethane；2-[2-(1H-indol-2-yl)ethyl]-1H-indole
• CAS: 144445-47-6
• 化学式: C₁₈H₁₆N₂
• 分子量: 260.338
• InChiKey: SQHYMROYVZIGDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,2-bis(1H-indol-2-yl)ethane 在 sodium tetrahydroborate 、 cobalt (III) fluoride 作用下， 以 乙醇 为溶剂， 反应 30.0h， 生成 2-(Trifluoromethyl)-10,15-diazapentacyclo[12.7.0.03,11.04,9.016,21]henicosa-1(14),3(11),4,6,8,12,16,18,20-nonaene
  参考文献：
  名称：

  Reactions of 1,2-Bis(1H-indol-2-yl)ethane: Formation of Indolo[2,3-c]carbazole and Cyclohept[1,2-b:5,4-b′]bisindole Derivatives

  摘要：

  1,2-Bis(1H-indol-2-yl)ethane (9) has been prepared and converted into indolo[2,3-c]carbazole (8) using palladium acetate in refluxing acetic acid. Reaction of 9 with CoF3 in hot TFA led to isolation of cyclohept[1,2-b:5,4-b']bisindole derivatives 11 and 12, which could be elaborated into further derivatives. Treatment of 9 with orthoesters, aldehydes and ketones under acidic conditions afforded additional bisindoles containing a seven-membered ring. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00100-9
• 作为产物：
  描述：

  2-甲基吲哚 以37%的产率得到1,2-bis(1H-indol-2-yl)ethane
  参考文献：
  名称：

  Reactions of 1,2-Bis(1H-indol-2-yl)ethane: Formation of Indolo[2,3-c]carbazole and Cyclohept[1,2-b:5,4-b′]bisindole Derivatives

  摘要：

  1,2-Bis(1H-indol-2-yl)ethane (9) has been prepared and converted into indolo[2,3-c]carbazole (8) using palladium acetate in refluxing acetic acid. Reaction of 9 with CoF3 in hot TFA led to isolation of cyclohept[1,2-b:5,4-b']bisindole derivatives 11 and 12, which could be elaborated into further derivatives. Treatment of 9 with orthoesters, aldehydes and ketones under acidic conditions afforded additional bisindoles containing a seven-membered ring. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00100-9

文献信息

• Homoarcyriaflavin:  Synthesis of Ring-Expanded Arcyriaflavin Analogues
  作者：Siavosh Mahboobi、Thomas Burgemeister、Stefan Dove、Sabine Kuhr、Alfred Popp

  DOI：10.1021/jo981926g

  日期：1999.10.1

  The construction of the ring-expanded carbazole system, forming arcyriaflavin homologues, is efficiently accomplished by the reaction of 2,2'-bridged bis-indoles with 3,4-dibromo-2,5-dihydro-1H-2,5-pyrroledione derivatives under Grignard conditions. A ring size of up to nine members in the central ring is achievable. Substitutions either at the indole system or at the imide-N are also possible. The

  通过形成2,2'-桥联的双吲哚与3,4-二溴-2,5-二氢-1H-2,5-吡咯二酮的反应可以有效地完成形成arcyriaflavin同系物的扩环咔唑系统的构建。格氏条件下的衍生品。中心环中最多可以有9个成员。也可以在吲哚体系或酰亚胺-N处取代。通过核磁共振，X射线和半经验量子化学计算方法研究了均硬环黄素作为刚性硬环黄素与柔性硬环红素之间的交联结构。
• Studies on the nucleophilic addition to 3,5-disubstituted pyridinium salts
  作者：Rodolfo Lavilla、Teresa Gotsens、Sonia Rodríguez、Joan Bosch

  DOI：10.1016/s0040-4020(01)88234-x

  日期：1992.1

  The reactivity of pyridinium salts 2 towards nucleophiles has been studied. The interaction with enolates derived from esters 1 gave only trace amounts of the expected compounds 3. Irreversible-type additions, however, allowed the preparation of indolyldihydropyridines 8 and 9 with high yields. Reaction of organometallic 10 with salt 2c, followed by acidic cyclization, afforded tetracycle 12.

  已经研究了吡啶鎓盐2对亲核试剂的反应性。与衍生自酯1的烯醇化物的相互作用仅产生痕量的预期化合物3。然而，不可逆型添加使得可以高产率制备吲哚基二氢吡啶8和9。有机金属10与盐2c反应，然后进行酸性环化，得到四环化合物12。
• US6531241B1
  申请人：——

  公开号：US6531241B1

  公开（公告）日：2003-03-11
• [EN] CYCLIC DELOCALIZED CATIONS CONNECTED BY SPACER GROUPS<br/>[FR] CATIONS DELOCALISES CYCLIQUES CONNECTES PAR DES GROUPES D'ESPACEMENT
  申请人：COVALENT ASSOCIATES INC

  公开号：WO2001004097A2

  公开（公告）日：2001-01-18

  Cyclic delocalized cations joined together by spacer groups, with anions of equal number to cations to maintain charge neutrality, are disclosed. These spacer groups may be organic or inorganic in origin and may vary in length. The spacer groups may be saturated, containing single bonds, or may be unsaturated, containing double and triple bonds. With appropriate design these materials can have melting and glass transition temperatures below, around, and above room temperature. The lyophobic character of these materials may be adjusted, providing unique properties. These materials are well suited for use as electrolytes, lubricants, solvents for extractions and for running reactions, biphase catalysis media, media for electroluminescent and electrochromic devices.
• Reactions of 1,2-Bis(1H-indol-2-yl)ethane: Formation of Indolo[2,3-c]carbazole and Cyclohept[1,2-b:5,4-b′]bisindole Derivatives
  作者：Jan Bergman、Tomasz Janosik、Larisa Yudina、Eric Desarbre、Göran Lidgren、Lennart Venemalm

  DOI：10.1016/s0040-4020(00)00100-9

  日期：2000.3

  1,2-Bis(1H-indol-2-yl)ethane (9) has been prepared and converted into indolo[2,3-c]carbazole (8) using palladium acetate in refluxing acetic acid. Reaction of 9 with CoF3 in hot TFA led to isolation of cyclohept[1,2-b:5,4-b']bisindole derivatives 11 and 12, which could be elaborated into further derivatives. Treatment of 9 with orthoesters, aldehydes and ketones under acidic conditions afforded additional bisindoles containing a seven-membered ring. (C) 2000 Elsevier Science Ltd. All rights reserved.