methyl 1-(triisopropylsilyl)-1H-indole-3-carboxylate | 181780-85-8

• 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: methyl 1-(triisopropylsilyl)-1H-indole-3-carboxylate
• 英文别名: Methyl 1-tri(propan-2-yl)silylindole-3-carboxylate
• CAS: 181780-85-8
• 化学式: C₁₉H₂₉NO₂Si
• 分子量: 331.53
• InChiKey: ALZJOADVZGVFCM-UHFFFAOYSA-N

物化性质

• 沸点：
  368.1±25.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.45
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 1-(triisopropylsilyl)-1H-indole-3-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 吲哚-3-甲酸甲酯
  参考文献：
  名称：

  3-Lithio-1-(triisopropylsilyl)indole. Preparation and Reactions with Electrophilic Reagents

  摘要：

  DOI：

  10.3987/com-96-7504
• 作为产物：
  描述：

  三异丙基氯硅烷 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 叔丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 正戊烷 为溶剂， 反应 2.67h， 生成 methyl 1-(triisopropylsilyl)-1H-indole-3-carboxylate
  参考文献：
  名称：

  3-Lithio-1-(triisopropylsilyl)indole. Preparation and Reactions with Electrophilic Reagents

  摘要：

  DOI：

  10.3987/com-96-7504

文献信息

• Preparation of 3,4-enynoindoles via directed lithiation and application to the synthesis of 3,4-carbocycloindoles
  作者：Leticia Pérez-Serrano、Luis Casarrubios、Gema Domı́nguez、Guillermo Freire、Javier Pérez-Castells

  DOI：10.1016/s0040-4020(02)00525-2

  日期：2002.7

  Lithiation at C4 of the indole nucleus is readily directed by several functional groups. The 4-substituted indoles thus obtained are transformed into suitable substrates for metathesis reactions. Ring-closing metathesis effected on these compounds lead to skeletons related to several indole alkaloids.

  几个官能团很容易指导吲哚核C4处的锂化。如此获得的4-取代的吲哚被转化为用于复分解反应的合适的底物。对这些化合物进行的闭环易位导致了与几种吲哚生物碱有关的骨架。
• Oxazole Synthesis by Sequential Asmic-Ester Condensations and Sulfanyl–Lithium Exchange–Trapping
  作者：Louis G. Mueller、Allen Chao、Embarek Alwedi、Maanasa Natrajan、Fraser F. Fleming

  DOI：10.1021/acs.orglett.1c00288

  日期：2021.2.19

  Oxazoles are rapidly assembled through a sequential deprotonation–condensation of Asmic, anisylsulfanylmethylisocyanide, with esters followed by sulfanyl–lithium exchange–trapping. Deprotonating Asmic affords a metalated isocyanide that efficiently traps esters to afford oxazoles bearing a versatile C-4 anisylsulfanyl substituent. Interchange of the anisylsulfanyl substituent is readily achieved through

  恶唑通过 Asmic、茴香硫基甲基异氰化物与酯的顺序去质子化 - 缩合快速组装，然后是硫烷基 - 锂交换 - 捕获。去质子化 Asmic 可提供金属化异氰化物，可有效捕获酯类，从而提供带有通用 C-4 苯硫基取代基的恶唑。通过一流的硫-锂交换-亲电捕获序列可以很容易地实现茴香硫基取代基的交换，其多功能性在生物活性天然产物链绿素的三步合成中得到了说明。
• Total Synthesis of Verruculogen and Fumitremorgin A Enabled by Ligand-Controlled C–H Borylation
  作者：Yu Feng、Dane Holte、Jochen Zoller、Shigenobu Umemiya、Leah R. Simke、Phil S. Baran

  DOI：10.1021/jacs.5b07154

  日期：2015.8.19

  Verruculogen and fumitremorgin A are bioactive alkaloids that contain a unique eight-membered endoperoxide. Although related natural products such as fumitremorgins B and C have been previously synthesized, we report the first synthesis of the more complex, endoperoxide-containing members of this family. A concise route to verruculogen and fumitremorgin A relied not only on a hydroperoxide/indole hemiaminal cyclization, but also on the ability to access the seemingly simple starting material, 6-methoxytryptophan. An iridium-catalyzed C-H borylation/Chan-Lam procedure guided by an N-TIPS group enabled the conversion of a tryptophan derivative into a 6-methoxytryptophan derivative, proving to be a general way to functionalize the C6 position of an N,C3-disubstituted indole for the synthesis of indole-containing natural products and pharmaceuticals.
• Progress toward Synthesis of Diazonamide A. Preparation of a 3-(Oxazol-5-yl)-4-trifluoromethylsulfonyloxyindole and Its Use in Biaryl Coupling Reactions
  作者：Edwin Vedejs、David A. Barda

  DOI：10.1021/ol005548p

  日期：2000.4.1

  The synthesis of a 3-oxazol-5-yl-indole-4-triflate is described, featuring a Scholkopf reaction to prepare the oxazole. In addition, the participation of this intermediate in biaryl coupling reactions toward the total synthesis of the natural product diazonamide A is presented.