5-methoxy-3-pentyl-1H-indole | 160428-53-5

• 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: 5-methoxy-3-pentyl-1H-indole
• 英文别名: 5-methoxy-2-pentylindole
• CAS: 160428-53-5
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: YIWLQYGJKFCTKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-methoxy-3-pentyl-1H-indole 、 乙硫醇 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到5-ethylthio-3-pentylindole
  参考文献：
  名称：

  Functionalisation of the alkoxy group of alkyl aryl ethers. Demethylation, alkylthiolation and reduction of 5-methoxyindoles

  摘要：

  In the presence of AlX(3)-RSH three kinds of reactions may take place with 5-methoxy indoles : demethylation, alkylthiolation and reduction. The two latter reactions have never been observed to the present, with such reagents. Considerable improvement in the selective demethylation was found when PhCH(2)SH replaced EtSH previously used in such transformations. Factors leading to selective alkylthiolations or reductions are shown and mechanisms are proposed to explain these new reactions.

  DOI：

  10.1016/s0040-4020(01)89350-9
• 作为产物：
  描述：

  3-氯-4-甲氧基苯胺 在 sodium amide 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 叔丁醇 、 苯 为溶剂， 反应 48.0h， 生成 5-methoxy-3-pentyl-1H-indole
  参考文献：
  名称：

  Aggregative activation and heterocyclic chemistry I complex bases promoted arynic cyclisation of imines or enaminoketones; regiochemical synthesis of indoles

  摘要：

  The complex base NaNH2-t-BuONa allowed expeditious syntheses of indoles by arynic cyclisation of imines or enaminoketones prepared from halogeno anilines and carbonyl derivatives. Unstable imines may be used without purification, complex bases being unsensitive to impurities. It is showed that this kind of reaction may be applied to mixture of substrates suitably halogenated on the benzene ring. Formation of three components aggregates is proposed to explain a number of observations.

  DOI：

  10.1016/s0040-4020(01)89304-2

文献信息

• New Organolithium Addition Methodology to Diversely Functionalized Indoles
  作者：Claire M. Coleman、Donal F. O'Shea

  DOI：10.1021/ja034283h

  日期：2003.4.1

  A novel synthetic approach to diversely functionalized indoles is described. Boc-protected ortho-aminostyrenes undergo an alkyllithium addition reaction, thereby generating a lithiated intermediate, which upon reaction with specific electrophiles sets up a cascade reaction process between the reacted electrophile and ortho-amino substituent, facilitating an in situ ring closure, followed by dehydration

  描述了一种用于不同功能化吲哚的新型合成方法。Boc 保护的邻氨基苯乙烯发生烷基锂加成反应，从而生成锂化中间体，该中间体与特定亲电试剂反应后，在反应的亲电试剂和邻氨基取代基之间建立级联反应过程，促进原位闭环，然后脱水，生成吲哚环系统。这种方法可以通过合成一系列 3,5-、1,3,5- 和 2,3,5- 取代的吲哚来证明。
• Indole Synthesis by Controlled Carbolithiation of <i>o</i>-Aminostyrenes
  作者：Albane Kessler、Claire M. Coleman、Patchanee Charoenying、Donal F. O'Shea

  DOI：10.1021/jo048723e

  日期：2004.11.1

  An effective synthesis of the functionalized indole ring system has been developed from substituted o-aminostyrene starting material. Our methodology involves a novel cascade reaction sequence of alkyllithium addition to the styrene double bond and subsequent trapping of the intermediate organolithium with a suitable electrophile, followed by an in situ ring closure and dehydration to generate the indole ring. This new reaction sequence allows for the introduction of molecular diversity at all positions on the indole scaffold. The procedure was shown to be successful with a range of both C and N substituents on the o-aminostyrenes. The reaction sequence was tolerant to the reactivity range of alkyllithiums such as tert-, sec-, and n-butyllithium. The electrophiles used were DMF, which generated indole products with C-2 unsubstituted, and nitriles, which incorporated the nitrile substituent at C-2. The o-aminostyrene starting materials were generated by a Pd-catalyzed cross-coupling reaction of a vinyl boronic acid equivalent with the readily available substituted o-bromoanilines.