3,3'-(pentane-3,3-diyl)bisindole | 886620-73-1

• 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: 3,3'-(pentane-3,3-diyl)bisindole
• 英文别名: 3,3-(3,3'-diindolyl)pentane；diEtDIM；3-[3-(1H-indol-3-yl)pentan-3-yl]-1H-indole
• CAS: 886620-73-1
• 化学式: C₂₁H₂₂N₂
• 分子量: 302.419
• InChiKey: FOFQJGNNCBWWPG-UHFFFAOYSA-N

物化性质

• 沸点：
  518.3±30.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  吲哚 、 3-戊酮 在 potassium hydrogensulfate 作用下， 以 甲醇 、 水 为溶剂， 反应 40.0h， 以91%的产率得到3,3'-(pentane-3,3-diyl)bisindole
  参考文献：
  名称：

  Enhancement of Chemically-Induced HL-60 Cell Differentiation by 3,3'-Diindolylmethane Derivatives

  摘要：

  3,3′-二吲哚甲烷（DIM，1）及其衍生物已被制备，并分析了它们对化学诱导的HL-60细胞分化的增强效应。在所制备的化合物中，IndDIM（12）显示出对HL-60细胞分化最强有力的增强作用，这种分化是由包括视黄酸、1,25-二羟维生素D3、12-O-十四烷酰佛波醇-13-乙酸酯和二甲基亚砜在内的化学物质诱导的。

  DOI：

  10.1248/cpb.57.536

文献信息

• Hydrated ferric sulfate-catalyzed reactions of indole with aldehydes, ketones, cyclic ketones, and chromanones: Synthesis of bisindoles and trisindoles
  作者：Wayland E. Noland、Honnaiah Vijay Kumar、Grant C. Flick、Cole L. Aspros、Jong Hyeon Yoon、Andre C. Wilt、Nasim Dehkordi、Sheng Thao、Andrew K. Schneerer、Siming Gao、Kenneth J. Tritch

  DOI：10.1016/j.tet.2017.05.061

  日期：2017.7

  Hydrated ferric sulfate [Fe2(SO4)3·xH2O] has been found to be an efficient catalyst for condensation of bisindoles or trisindoles with aliphatic or aryl aldehydes and ketones including methyl and ethyl-alkyl ketones, methyl aryl ketones, cyclic ketones, and 4-chromanones in 19–96% yields. Trisindoles and 2,2'-alkylidenebisindoles were obtained from indole-3-carbaldehydes or 3-methylindole in 72–84% yields

  水合硫酸铁[Fe 2（SO 4）3 · x H 2 O]被发现是双吲哚或三吲哚与脂族或芳基醛和酮（包括甲基和乙基烷基酮，甲基芳基酮）缩合的有效催化剂，环酮和4-chromanones的产率为19-96％。从吲哚-3-甲醛或3-甲基吲哚获得三吲哚和2,2'-亚烷基双吲哚，产率为72–84％。总共使用了43种底物，得到33种双吲哚，3种三吲哚和一种2：2产物。其中有十七个是新的。用Fe 2（SO 4）3 · x加热乙醇悬浮液可获得最佳结果。H 2 O负载量为60 mg / mmol亲电试剂。反应时间通常为1-4小时，而受阻亲电试剂则需要8-24小时。这些条件足够强以促进吲哚与底物的2：1缩合，而不会形成高阶副产物，几乎没有例外。该策略的特征在于催化剂对各种官能团的耐受性，易于获得的起始原料，简单的操作，温和的反应条件以及对环境友好。
• An efficient and green synthetic protocol for the preparation of bis(indolyl)methanes catalyzed by H6P2W18O62·24H2O, with emphasis on the catalytic proficiency of Wells-Dawson versus Keggin heteropolyacids
  作者：Reza Tayebee、Farzaneh Nehzat、Esmail Rezaei-Seresht、Farokhzad Z. Mohammadi、Ezzat Rafiee

  DOI：10.1016/j.molcata.2011.09.029

  日期：2011.12

  A simple, atom economy, and a highly well-organized green protocol has been developed for the synthesis of bis(indolyl)methanes. Wells-Dawson diphosphooctadecatungsticacid (H6P2W18O62 center dot 24H(2)O) was employed as a proficient, a highly water tolerant, and green heteropolyacid catalyst for the electrophilic substitution reactions of indole with various aldehydes and ketones to afford the corresponding bis(indolyl)methane derivatives under solvent-free condition. Presumably, discrepancies observed in the reactivity patterns of various heteropolyacids would be explained concerning differences in the acidity, structural diversity, and dissimilarities in the approach of the substrates to the bulk of the heteropolyacid catalysts. It is confirmed that the identity of the catalyst was retained almost completely during the catalytic reaction. (C) 2011 Elsevier B.V. All rights reserved.
• DIINDOLYLMETHANE AND C-SUBSTITUTED DIINDOLYLMETHANE COMPOSITIONS AND METHODS FOR THE TREATMENT OF MULTIPLE CANCERS
  申请人：The Texas A & M University System

  公开号：EP1328513A2

  公开（公告）日：2003-07-23
• [EN] DIINDOLYLMETHANE AND C-SUBSTITUTED DIINDOLYLMETHANE COMPOSITIONS AND METHODS FOR THE TREATMENT OF MULTIPLE CANCERS<br/>[FR] COMPOSITIONS DE DIINDOLYLMETHANE ET DE DIINDOLYLMETHANE C-SUBSTITUE ET PROCEDES DE TRAITEMENT DE CANCERS MULTIPLES
  申请人：TEXAS A & M UNIV SYS

  公开号：WO2002028832A2

  公开（公告）日：2002-04-11

  Disclosed are methods and compositions for the treatment of a wide array of cancers and tumors. In illustrative embodiments, diindolylmethanes, C-substituted diindolylmethanes, and analogs thereof have been described, which when administered either alone, or in combination with other anti-cancer or anti-tumorigenic compounds, provide new therapies for the treatment cancer.
• Enhancement of Chemically-Induced HL-60 Cell Differentiation by 3,3'-Diindolylmethane Derivatives
  作者：Tomomi Noguchi-Yachide、Masashi Tetsuhashi、Hiroshi Aoyama、Yuichi Hashimoto

  DOI：10.1248/cpb.57.536

  日期：——

  3,3′-Diindolylmethane (DIM, 1) and its derivatives have been prepared, and their enhancing effects on chemically-induced HL-60 cell differentiation were analyzed. Among the prepared compounds, IndDIM (12) showed the most potent enhancing effect on HL-60 cell differentiation induced by chemicals, including retinoids, 1,25-dihydroxyvitamin D3, 12-O-tetradecanoyl phorbol-13-acetate and dimethyl sulfoxide.

  3,3′-二吲哚甲烷（DIM，1）及其衍生物已被制备，并分析了它们对化学诱导的HL-60细胞分化的增强效应。在所制备的化合物中，IndDIM（12）显示出对HL-60细胞分化最强有力的增强作用，这种分化是由包括视黄酸、1,25-二羟维生素D3、12-O-十四烷酰佛波醇-13-乙酸酯和二甲基亚砜在内的化学物质诱导的。