2-lithio-1-methylindole | 54852-26-5

• 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: 2-lithio-1-methylindole
• CAS: 54852-26-5
• 化学式: C₉H₈LiN
• 分子量: 137.11
• InChiKey: GEWBZDKBCQBTNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-lithio-1-methylindole 在 1,4-双(二苯基膦丁烷)二氯化钯 magnesium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 三甲基-[1-(1-甲基吲哚-2-基)乙烯基]硅烷
  参考文献：
  名称：

  An efficient route to heteroarene-substituted vinyl- and allyl-silanes via palladium-phosphine complex catalyzed cross-coupling

  摘要：

  DOI：

  10.1016/s0040-4039(01)91154-2
• 作为产物：
  描述：

  2-溴-1-甲基-1H-吲哚 在 正丁基锂 作用下， 以 正己烷 为溶剂， 生成 2-lithio-1-methylindole
  参考文献：
  名称：

  Synthesis of Benzosiloles by Intramolecular anti-Hydroarylation via ortho-C–H Activation of Aryloxyethynyl Silanes

  摘要：

  Straightforward synthesis of benzosiloles was achieved by the invention of Pd/acid-catalyzed intramolecular anti-hydroarylation of aryloxyethynyl(aryl)-silanes via ortho-C-H bond activation. The aryloxy group bound to the ethynyl carbon is the key factor for this transformation.

  DOI：

  10.1021/jacs.7b08055

文献信息

• Synthesis of Sulfonyl Azides
  作者：Alan Katritzky、Khalid Widyan、Kapil Gyanda

  DOI：10.1055/s-2008-1072568

  日期：2008.4

  1-(Alkylsulfonyl)- and 1-(arylsulfonyl)benzotriazoles react with sodium azide in acetonitrile to give the corresponding alkanesulfonyl and arenesulfonyl azides.

  1-（烷基磺酰基）和1-（芳基磺酰基）苯并三氮唑与氰化钠在丙酮腈中反应，生成相应的烷基磺酰基和芳基磺酰基叠氮化合物。
• Tandem organometallic addition reactions to N-methoxy-ureas and urethanes in the preparation of unsymmetrical and symmetrical ketones
  作者：Dennis J. Hlasta、John J. Court

  DOI：10.1016/s0040-4039(00)99576-5

  日期：——

  The use of the novel reagents 1a–c for the synthesis of ketones in a one pot reaction is described. An interesting leaving group effect was discovered in the fragmentation of the proposed complexes 2 to the intermediate N-methoxyamides 3.

  描述了在单罐反应中使用新型试剂1a-c合成酮的方法。在提议的复合物2裂解为中间体N-甲氧基酰胺3的过程中发现了一个有趣的离去基团效应。
• Synthesis of 4-substituted 2-(4-methylpiperazino)pyrimidines and quinazoline analogs as serotonin 5-HT_2Areceptor ligands
  作者：Jaroslaw Saczewski、Aldona Paluchowska、Jeffrey Klenc、Elizabeth Raux、Samuel Barnes、Shannon Sullivan、Beata Duszynska、Andrzej J. Bojarski、Lucjan Strekowski

  DOI：10.1002/jhet.236

  日期：2009.11

  The addition reaction of lithium reagents to the 4 position of 2‐chloropyrimidine or 2‐chloroquinazoline followed by oxidation of the resultant dihydro intermediate product is a powerful tool for the synthesis of 4‐substituted 2‐chloropyrimidines or 2‐chloroquinazolines. 4‐Vinyl derivatives undergo a conjugate nucleophilic addition across the vinyl group. A nucleophilic displacement of chloride in

  将锂试剂加成至2-氯嘧啶或2-氯喹唑啉的4位反应，然后氧化所得的二氢中间产物，是合成4取代2-氯嘧啶或2-氯喹唑啉的有力工具。4-乙烯基衍生物在整个乙烯基上进行共轭亲核加成。通过用4-甲基哌嗪处理，4-取代的2-氯嘧啶或2-氯喹唑啉中氯的亲核取代提供了作为5-羟色胺5-HT 2A受体拮抗剂的化合物。J.杂环化​​学，（2009）。
• Functionalized organolithium reagents in the synthesis of chiral ligands for catalytic enantioselective addition of diethylzinc to aldehydes
  作者：Georgi M. Dobrikov、Irena Philipova、Rositsa Nikolova、Boris Shivachev、Angel Chimov、Vladimir Dimitrov

  DOI：10.1016/j.poly.2012.06.090

  日期：2012.9

  were prepared and added to chiral bicyclic ketones (1R-(+)-camphor analogue 2 and 1R-(−)-fenchone 3), resulting in the preparation of a small “library” of chiral aminoalcohols able to serve as ligands in metal mediated asymmetric synthesis. The configuration of the chiral ligands was approved by applying advanced NMR experiments. The absolute configurations of 1,2-disubstituted planar chiral ferrocene-based

  摘要制备了一系列功能化的有机锂化合物，并将其添加到手性双环酮（1R-（+）-樟脑类似物2和1R-（--- fenchone 3）中，从而制备了一个小的“手性”氨基醇醇“库”在金属介导的不对称合成中用作配体。手性配体的构型通过应用先进的NMR实验得到了认可。通过NMR实验确定1，2-二取代的平面手性二茂铁基氨基醇15、18和19的绝对构型，并通过X射线晶体学证实。测试了新的手性配体作为向苯甲醛中添加二乙基锌的预催化剂。反应以优异的转化率和中等程度的对映选择性进行。
• Novel Building Blocks: 1-Aryl-2-chloro-1-ethoxyethenes – Preparations and Transformations
  作者：Mitsuhiro Yoshimatsu、Miho Sakai、Eri Moriura

  DOI：10.1002/ejoc.200600863

  日期：2007.1

  We described here a simple method for the preparation of 1-aryl-2-chloro-1-ethoxyethenes 2a–u, which are prodrugs for Alzheimer's disease, by the reaction of dichloroacetaldehyde diethyl acetal with various aryl and alkenyllithium compounds in high yields. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  我们在此描述了一种通过二氯乙醛二乙基缩醛与各种芳基和烯基锂化合物高产率反应制备 1-芳基-2-氯-1-乙氧基乙烯 2a-u（阿尔茨海默病的前药）的简单方法。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)