2,3-dimethyl-3-(prop-2-en-1-yl)-3H-indole | 23569-47-3

• 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: 2,3-dimethyl-3-(prop-2-en-1-yl)-3H-indole
• 英文别名: 3-allyl-2,3-dimethyl-3H-indole；3-allyl-2,3-dimethyl-3H-indole；3-Allyl-2,3-dimethyl-3H-indol；2,3-Dimethyl-3-allyl-indolenin；3-Allyl-2,3-dimethyl-3H-indol；2,3-Dimethyl-3-prop-2-enylindole
• CAS: 23569-47-3
• 化学式: C₁₃H₁₅N
• 分子量: 185.269
• InChiKey: FASKUHGWFQJVCR-UHFFFAOYSA-N

物化性质

• 沸点：
  261.2±33.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3-dimethyl-3-(prop-2-en-1-yl)-3H-indole 以 乙醇 、 氯仿 、 乙腈 为溶剂， 反应 123.0h， 生成 6-[2-[1-(2-Hydroxyethyl)-3-methyl-3-prop-2-enylindol-2-ylidene]ethylidene]-4-nitrocyclohexa-2,4-dien-1-one
  参考文献：
  名称：

  Synthesis of 3′-allylindoline spirobenzopyrans derived from 3-allyl-3H-indoles

  摘要：

  In this study, 8 new spirobenzopyrans were synthesized. A novel, three-step, facile route for the synthesis of 3'-allylindoline spirobenzopyrans via 3-allyl-3H-indoles was developed. The newly synthesized spirobenzopyrans were evaluated for their photochromic properties. The presence of an allyl moiety at the 3' position did not disturb the photochromic response. The steric effects of the diallyl groups at the 3' position affected the interconversion between colored and colorless forms. Therefore, the allyl chain in 3'-allylindoline spirobenzopyrans can be utilized to attach these compounds to a molecular matrix. Consequently, this synthetic methodology could be readily applied to the creation of new photo-switchable materials. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.121
• 作为产物：
  描述：

  allyl 2,3-dimethyl-1H-indole-1-carboxylate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三(2-呋喃基)膦 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以95%的产率得到2,3-dimethyl-3-(prop-2-en-1-yl)-3H-indole
  参考文献：
  名称：

  N-Alloc 和 N-Cbz 吲哚的钯催化脱羧烯丙基化和苄基化

  摘要：

  分别从相应的N- alloc 和N- Cbz 吲哚开始，钯催化的吲哚脱羧 C3-烯丙基化和 C3-苄基化的一组通用方法被报道。这种化学反应可以很容易地获得各种功能化的假吲哚，收率非常好。一种串联工艺，其中钯催化的烯丙基化化学与 Mizoroki-Heck 反应相结合，为肉桂化产品提供了一条简单的途径。

  DOI：

  10.1021/ol400334u

文献信息

• Palladium Catalyzed Decarboxylative Rearrangement of <i>N</i>-Alloc Indoles
  作者：Jun Chen、Matthew J. Cook

  DOI：10.1021/ol400110c

  日期：2013.3.1

  A highly efficient palladium catalyzed decarboxylative allylic rearrangement of alloc indoles has been developed. This can also be combined with a Suzuki–Miyaura cross-coupling reaction in a single pot transformation. Substituted alloc groups and benzylic variants have also been demonstrated alongside promising initial results on the enantioselective variant.

  已经开发了分配吲哚的高效钯催化的脱羧烯丙基重排。也可以在单个罐转化中将其与Suzuki-Miyaura交叉偶联反应结合使用。除了对映体选择性变体的有希望的初步结果外，还证明了取代的分配基团和苄基变体。
• Platinum-Catalyzed Allylation of 2,3-Disubstituted Indoles with Allylic Acetates
  作者：Bai-Jing Peng、Wen-Ting Wu、Shyh-Chyun Yang

  DOI：10.3390/molecules22122097

  日期：——

  allyation of nucleophiles was an established and efficient way, which has been applied to medicinal and organic chemistry. In our research, the platinum-catalyzed 2,3-disubstitued indoles with allylic acetates was investigated under different conditions. Herein, we established a simple, convenient, and efficient method, which afforded high yield of allylated indoles.

  鉴于杂环吲哚衍生物的重要性，人们付出了很多努力来开发在 N1 和 C3 位点上对吲哚核进行功能化的方法。此外，铂催化的亲核试剂烯丙基化是一种既定且有效的方法，已应用于药物和有机化学。在我们的研究中，在不同条件下研究了铂催化的2,3-二取代吲哚与烯丙乙酸酯的反应。在此，我们建立了一种简单、方便、高效的方法，可以获得高产率的烯丙基化吲哚。
• Synthesis of 3,3′-Disubstituted Indolenines Utilizing the Lewis Acid Catalyzed Alkylation of 2,3-Disubstituted Indoles with Trichloroacetimidates
  作者：John Chisholm、Arijit Adhikari、Léa Radal

  DOI：10.1055/s-0036-1588491

  日期：2017.10

  electrophiles for the selective C3-alkylation of 2,3-disubstituted indoles to provide 3,3'-disubstituted indolenines. These indolenines are common synthetic intermediates that are often utilized in the synthesis of complex molecules. Effective reaction conditions utilizing Lewis acid catalysts have been determined, and the scope of the reaction with respect to indole and imidate reaction partner has been

  三氯乙酰亚胺酯可作为有效的亲电子试剂，用于选择性 C3-烷基化 2,3-二取代吲哚以提供 3,3'-二取代吲哚啉。这些假吲哚是常见的合成中间体，常用于复杂分子的合成。已经确定了使用路易斯酸催化剂的有效反应条件，并研究了与吲哚和亚胺酸酯反应伙伴有关的反应范围。这种化学反应提供了一种替代碱促进和过渡金属催化的方法，后者更常用于获取类似的假吲哚。
• <i>N</i>-Indolyltriethylborate: A Useful Reagent for Synthesis of C3-Quaternary Indolenines
  作者：Aijun Lin、Jiong Yang、Mohamed Hashim

  DOI：10.1021/ol4005992

  日期：2013.4.19

  N-Indolyltriethylborate was found to be a useful reagent for dearomatizing C3-alkylation of 3-substituted indoles with both activated and nonactivated alkyl halides to give C3-quaternary indolenines, pyrroloindolines, furoindoline, and hexahydropyridoindoline under mild reaction conditions. The utility of these reagents was demonstrated in the syntheses of a pyrroloindoline-4-cholestene hybrid and debromoflustramine B.
• Fishwick, Colin W.G.; Jones, Andrew D.; Mitchell, Michael B., Heterocycles, 1991, vol. 32, # 4, p. 685 - 692
  作者：Fishwick, Colin W.G.、Jones, Andrew D.、Mitchell, Michael B.

  DOI：——

  日期：——