3-(3-phenylallyl)-1H-indole | 201813-90-3

• 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: 3-(3-phenylallyl)-1H-indole
• 英文别名: 3-[(E)-3-phenylprop-2-enyl]-1H-indole
• CAS: 201813-90-3
• 化学式: C₁₇H₁₅N
• 分子量: 233.313
• InChiKey: AXCLFGUNLKPCCD-RMKNXTFCSA-N

物化性质

• 熔点：
  99.6-100.1 °C
• 沸点：
  420.6±14.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-(3-phenylallyl)-1H-indole 在 正丁基锂 、 N-叔丁基苯硫腈氯化物 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 (3Z)-3-[(E)-3-phenylprop-2-enylidene]indole
  参考文献：
  名称：

  具有碳亲核试剂的3-苄基和3-烯丙基吲哚的一锅氧化碳-碳键形成

  摘要：

  在-78℃下产生假吲哚由3-苄基或3-吲哚烯丙基通过脱氢用ñ -叔-butylbenzenesulfinimidoyl氯化物，和通过处理这些假吲哚形成的碳-碳键在-78℃下，在一锅方式与各种碳亲核试剂，例如活性亚甲基化合物或有机铜酸盐。

  DOI：

  10.1016/j.tet.2008.03.033
• 作为产物：
  描述：

  o-ethynyltrifluoroacetanilide 在 四(三苯基膦)钯 、 tris(dibenzylideneacetone)dipalladium (0) 、 potassium carbonate 、 丁基二苯基膦 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 25.0h， 生成 3-(3-phenylallyl)-1H-indole
  参考文献：
  名称：

  Palladium-Catalyzed Cyclization of o-Alkynyltrifluoroacetanilides with Allyl Esters. A Regioselective Synthesis of 3-Allylindoles

  摘要：

  The reaction of readily available o-alkynyltrifluoroacetanilides 1 with allyl esters provides a valuable new route to 3-allylindoles 3. Three basic procedures have been developed: a stepwise method based on the isolation of the N-allyl derivative 4 and its subsequent cyclization to 3 (procedure a), a one-pot reaction omitting the isolation of 4 (procedure b), and a procedure which most probably leads to the formation of 3 through a mechanism not involving the intermediacy of 4 (procedure c). In the presence of the electron-rich sterically encumbered ligand tris(2,4,6-trimethoxyphenyl)phosphine (ttmpp) the reaction exhibits remarkable regioselectivity and almost exclusive formation of 3-allylindoles with the indolyl moiety bound to the less substituted allyl terminus is usually observed. However, some loss of olefin geometry is observed.

  DOI：

  10.1021/jo971237p

文献信息

• Electrophilic Allylations and Benzylations of Indoles in Neutral Aqueous or Alcoholic Solutions
  作者：Martin Westermaier、Herbert Mayr

  DOI：10.1021/ol0618555

  日期：2006.10.1

  [reaction: see text] Indoles are allylated and benzylated in moderate to quantitative yield when stirred with allyl and benzyl halides in 80% aqueous acetone in the presence of NH(4)HCO(3) at room temperature.

  [反应：见正文]在室温下，在NH（4）HCO（3）存在下，与烯丙基和苄基卤化物在80％丙酮水溶液中搅拌时，吲哚被烯丙基化并以中等至定量的产率被苄基化。
• Benzylic Substitution of Gramines with Boronic Acids and Rhodium or Iridium Catalysts^†
  作者：Gabriela de la Herrán、Amaya Segura、Aurelio G. Csákÿ

  DOI：10.1021/ol063042m

  日期：2007.3.1

  Gramine-Mel salts were useful starting materials for the synthesis of 3-benzyl- and 3-allylindoles by the 1,4-addition of boronic acids to the C=C-C=N linkages generated in situ under Rh(I)-catalysis. On the other hand, under Ir(I) catalysis, the reaction of gramines with indoles was used to produce nonsymmetrical diindolylmethanes.
• Pd-Catalyzed C3-Selective Allylation of Indoles with Allyl Alcohols Promoted by Triethylborane
  作者：Masanari Kimura、Makoto Futamata、Ryutaro Mukai、Yoshinao Tamaru

  DOI：10.1021/ja0501161

  日期：2005.4.1

  Under palladium catalysis, Et3B nicely promotes allyl alcohols to undergo C3-selective allylation of indoles and tryptophan; the yields range 75-95%.
• Palladium-Catalyzed Cyclization of <i>o</i>-Alkynyltrifluoroacetanilides with Allyl Esters. A Regioselective Synthesis of 3-Allylindoles
  作者：Sandro Cacchi、Giancarlo Fabrizi、Paola Pace

  DOI：10.1021/jo971237p

  日期：1998.2.1

  The reaction of readily available o-alkynyltrifluoroacetanilides 1 with allyl esters provides a valuable new route to 3-allylindoles 3. Three basic procedures have been developed: a stepwise method based on the isolation of the N-allyl derivative 4 and its subsequent cyclization to 3 (procedure a), a one-pot reaction omitting the isolation of 4 (procedure b), and a procedure which most probably leads to the formation of 3 through a mechanism not involving the intermediacy of 4 (procedure c). In the presence of the electron-rich sterically encumbered ligand tris(2,4,6-trimethoxyphenyl)phosphine (ttmpp) the reaction exhibits remarkable regioselectivity and almost exclusive formation of 3-allylindoles with the indolyl moiety bound to the less substituted allyl terminus is usually observed. However, some loss of olefin geometry is observed.
• One-pot oxidative carbon–carbon bond formation of 3-benzylic and 3-allylic indoles with carbon nucleophiles
  作者：Jun-ichi Matsuo、Yumi Tanaki、Hiroyuki Ishibashi

  DOI：10.1016/j.tet.2008.03.033

  日期：2008.5

  Indolenines were generated at −78 °C from 3-benzylic or 3-allylic indoles by dehydrogenation with N-tert-butylbenzenesulfinimidoyl chloride, and a carbon–carbon bond was formed at −78 °C in a one-pot manner by treating these indolenines with various carbon nucleophiles such as active methylene compounds or organocuprates.

  在-78℃下产生假吲哚由3-苄基或3-吲哚烯丙基通过脱氢用ñ -叔-butylbenzenesulfinimidoyl氯化物，和通过处理这些假吲哚形成的碳-碳键在-78℃下，在一锅方式与各种碳亲核试剂，例如活性亚甲基化合物或有机铜酸盐。