1-(trimethylsilanyl)-2,3-dihydro-1H-indole | 114085-24-4

• 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: 1-(trimethylsilanyl)-2,3-dihydro-1H-indole
• 英文别名: N-trimethylsilylindoline；1-(Trimethylsilyl)-2,3-dihydro-1H-indole；2,3-dihydroindol-1-yl(trimethyl)silane
• CAS: 114085-24-4
• 化学式: C₁₁H₁₇NSi
• 分子量: 191.348
• InChiKey: WJYQETAXQOWOEJ-UHFFFAOYSA-N

物化性质

• 沸点：
  237.4±23.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-O-三苯甲基-2,3-O-异亚丙基-D-呋喃核糖 、 1-(trimethylsilanyl)-2,3-dihydro-1H-indole 在 2-氟-1-甲基吡啶翁对甲苯磺酸盐 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以90%的产率得到1-(5-O-triphenylmethyl-2,3-O-isopropylidene-α-D-ribofuranosyl)indoline
  参考文献：
  名称：

  Regioselective Glycosylation: Synthesis of α-Indoline Nucleosides

  摘要：

  Novel indoline ribonucleosides with the alpha-N-glycoside configuration are synthesized with very high regioselectivily in 90-96% yield, using TMS protected indolines and 2,3-O-(1-methylethylidene)-5-O-(triphenylmethyl)-alpha/beta-D-ribofuranose. The structures of these ribonucleosides were elucidated with X-ray crystallography as well as 2D (NOESY COSY and HMQC) NMR spectroscopy.

  DOI：

  10.1081/ncn-200067398
• 作为产物：
  描述：

  吲哚啉 、 N,O-双三甲硅基乙酰胺 以 乙腈 为溶剂， 反应 1.0h， 生成 1-(trimethylsilanyl)-2,3-dihydro-1H-indole
  参考文献：
  名称：

  由酰基氟和N-甲硅烷基胺合成酰胺的新方法

  摘要：

  N-甲硅烷基胺与水解稳定的酰基氟在温和条件下容易形成酰胺键。

  DOI：

  10.1016/s0040-4039(00)95601-6

文献信息

• Manganese-Catalyzed Regioselective Dehydrogenative C- versus N-Alkylation Enabled by a Solvent Switch: Experiment and Computation
  作者：Jannik C. Borghs、Viktoriia Zubar、Luis Miguel Azofra、Jan Sklyaruk、Magnus Rueping

  DOI：10.1021/acs.orglett.0c01270

  日期：2020.6.5

  base metal-catalyzed regioselective dehydrogenative alkylation of indolines using readily available alcohols as the alkylating reagent is reported. A single air- and moisture-stable manganese catalyst provides access to either C3- or N-alkylated indoles depending on the solvent used. Mechanistic studies indicate that the reaction takes place through a combined acceptorless dehydrogenation and hydrogen

  报道了使用容易获得的醇作为烷基化试剂的二氢吲哚的第一种贱金属催化的区域选择性脱氢烷基化。单一的空气和水分稳定的锰催化剂取决于所使用的溶剂，可提供C 3-或N-烷基化的吲哚的途径。机理研究表明，该反应通过无受体脱氢和氢自动转移策略的结合而发生。
• Tetrahydroquinolinyl Amido and Indolinyl Amido Complexes of Tantalum as Models for Substrate−Catalyst Adducts in Hydrodenitrogenation Catalysis
  作者：Peter A. Fox、Steven D. Gray、Michael A. Bruck、David E. Wigley

  DOI：10.1021/ic960298n

  日期：1996.1.1

  The reactions of TaCl5 with Me(3)SiNC(9)H(10) or LiNC9H10, where [NC9H10](-) = tetrahydroquinolinyl (the amido anion of tetrahydroquinoline), afford selective preparative routes to the complete series of amido halide complexes of tantalum(V) Ta(NC9H10)(n)Cl-5-n for n = 1-5 (compounds 1-5, respectively). The monokis(tetrahydroquinolinyl) complex is isolated as an ether adduct Ta(NC9H10)Cl-4(OEt(2)) while the complexes Ta(NC9H10)(n)Cl-5-n (n = 2-5) are found to be base-free, monomeric species. The related complexes of indolinyl [NC8H8](-) (the amido anion of indoline), Ta(NC8H8)(n)Cl-5-n(THF) for n = 1 (6) or 2 (7), have been prepared from TaCl5, Me(3)SiNC(8)H(8), and THF. An X-ray structural determination of Ta(NC9H10)(2)Cl-3 (2) reveals that it adopts a trigonal bipyramidal geometry with equatorial amido ligands that are closer to lying parallel (within) than perpendicular to the TBP equatorial plane. Routes to mixed-ligand aryloxide-amide complexes have been developed from either aryloxide or amido precursors but not from both. Thus, Ta(NC9H10)(OAr)Cl-3(OEt(2)) (8), where Ar = 2,6-(C6H3Pr2)-Pr-i, and Ta(NC8H8)(OAr)Cl-3(OEt(2)) (9) are available from reacting Ta(OAr)Cl-4(OEt(2)) with Me(3)SiNC(9)H(10) and Me(3)SiNC(8)H(8), respectively, while Ta(NC9H10)(2)(OAr)(2)Cl (10) is available from Ta(NC9H10)(2)Cl-3 (2) and excess LiOAr . OEt(2). The alkyl derivatives Ta(NC9H10)(OAr)Me(2)Cl (11), Ta(NC9H10)(OAr)Et(2)Cl (12), Ta(NC9H10)(2)(OAr)(2)Me (13), and Ta(NC9H10)Me(2)Cl(2) (14) are prepared from AlR(3) or ZnR(2) reagents and the appropriate precursor. Thermolyzing compounds 4, 5, and 11-14 in solution afforded no evidence for the formation of any eta(2)(N,C)-heterocyclic complexes arising from metalation of a NC9H10 ligand.
• Regioselective Glycosylation: Synthesis of <i>α</i>-Indoline Nucleosides
  作者：Kenneth L. Brown、Tilak Chandra、Shawn Zou、Edward J. Valente

  DOI：10.1081/ncn-200067398

  日期：2005.7.1

  Novel indoline ribonucleosides with the alpha-N-glycoside configuration are synthesized with very high regioselectivily in 90-96% yield, using TMS protected indolines and 2,3-O-(1-methylethylidene)-5-O-(triphenylmethyl)-alpha/beta-D-ribofuranose. The structures of these ribonucleosides were elucidated with X-ray crystallography as well as 2D (NOESY COSY and HMQC) NMR spectroscopy.
• A new synthesis of amides from acyl fluorides and N-silylamines
  作者：Sundaramoorthi Rajeswari、Robert J. Jones、Michael P. Cava

  DOI：10.1016/s0040-4039(00)95601-6

  日期：——

  Amide bonds are formed readily under mild conditions by the reaction of N-silylamines with the hydrolytically stable acyl fluorides.

  N-甲硅烷基胺与水解稳定的酰基氟在温和条件下容易形成酰胺键。