6-(Trimethylsilyl)-4-hexinyl-1-amine | 101195-68-0

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: 6-(Trimethylsilyl)-4-hexinyl-1-amine
• 英文别名: 6-(Trimethylsilyl)-4-hexynylamine；6-(Trimethylsilyl)hex-4-yn-1-amine；6-trimethylsilylhex-4-yn-1-amine
• CAS: 101195-68-0
• 化学式: C₉H₁₉NSi
• 分子量: 169.342
• InChiKey: KXVONVDQCLRRFU-UHFFFAOYSA-N

物化性质

• 沸点：
  196.8±20.0 °C(Predicted)
• 密度：
  0.847±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-(Trimethylsilyl)-4-hexinyl-1-amine 在 sodium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 4-Cyano-6-hydroxy-1-(6-trimethylsilanyl-hex-4-ynyl)-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Stereoselective sequential photochemical cycloaddition - iminium ion - propargylsilane cyclization. Synthesis of quinolizidines and pyrido [1,2-a]azepines

  摘要：

  Photochemical cycloaddition of the enaminecarbaldehydes 15 and 16 with the acrylic acid derivatives 20a-c gave the 2-hydroxytetrahydropyridines 21a-c and 24a-c, respectively which cyclize on treatment with trifluoroacetic acid or Lewis acids to furnish the quinolizidines 22a-c and pyrido[1,2-a]azepines 25a-c, respectively in good yields and with high 1,3-induced diastereoselectivity. Indolizidines 27 cannot be prepared by this method.

  DOI：

  10.1016/s0040-4020(01)88876-1
• 作为产物：
  描述：

  2-(4-戊炔氧基)四氢-2H-吡喃 在 正丁基锂 、 sodium azide 、 硫酸 、 水 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 58.5h， 生成 6-(Trimethylsilyl)-4-hexinyl-1-amine
  参考文献：
  名称：

  Stereoselective sequential photochemical cycloaddition - iminium ion - propargylsilane cyclization. Synthesis of quinolizidines and pyrido [1,2-a]azepines

  摘要：

  Photochemical cycloaddition of the enaminecarbaldehydes 15 and 16 with the acrylic acid derivatives 20a-c gave the 2-hydroxytetrahydropyridines 21a-c and 24a-c, respectively which cyclize on treatment with trifluoroacetic acid or Lewis acids to furnish the quinolizidines 22a-c and pyrido[1,2-a]azepines 25a-c, respectively in good yields and with high 1,3-induced diastereoselectivity. Indolizidines 27 cannot be prepared by this method.

  DOI：

  10.1016/s0040-4020(01)88876-1

文献信息

• The fluoride ion-induced intramolecular conjugate addition of propargylsilanes to dihydropyridones. A novel method for the stereoselective construction of azabicyclic ring systems
  作者：Magdalena Dziedzic、Grzegorz Lipner、José M. Illangua、Bartłomiej Furman

  DOI：10.1016/j.tet.2005.06.105

  日期：2005.9

  The fluoride ion-induced intramolecular conjugate addition of propargylsilanes to dihydropyridones is reported. Our results revealed that tetrabutylammonium triphenyldifluorosilicate (TBAT), an air-stable, non-hygroscopic fluoride ion source, catalyzes cyclocondensation to provide the corresponding 1-vinylidene indolizidines in a high yield as single isomers, while Lewis acid catalysts were ineffective

  据报道，氟离子诱导的炔丙基硅烷分子内共轭加成到二氢吡啶酮中。我们的结果表明，空气稳定的，非吸湿性的氟离子源四丁基三苯基二氟硅酸铵（TBAT）催化环化缩合反应以高产率提供相应的1-亚乙烯基吲哚并咪唑作为单一异构体，而路易斯酸催化剂无效。在产生具有更大环尺寸的化合物的反应中进一步研究了该方法的范围。在这些情况下，具有位于侧链的炔丙基硅烷的二氢吡啶酮进行环化，从而以显着较低的产率得到9-亚乙烯基喹嗪。
• Intramolecular reactions of acyclic n-acyliminium ions III silicon assisted cyclocondensation of glyoxylic esters to proline and pipecolic acid derivatives
  作者：Hendrik H Mooiweer、Henk Hiemstra、Hendrikus P Fortgens、W.Nico Speckamp

  DOI：10.1016/s0040-4039(00)95494-7

  日期：1987.1

  Cyclizations of acyclic N-acyliminium ions, generated from the adducts of formaldehyde, n-butyl glyoxylate or methyl glyoxylate with amines containing an allyl or propargyl silane as terminator, lead to 3-ethenyl and 3-ethenylidene substituted pyrrolidines and piperidines, some of which are structurally related to proline and pipecolic acid.

  由甲醛，乙醛酸正丁酯或乙醛酸甲酯与含有烯丙基或炔丙基硅烷作为终止剂的胺的加合物生成的无环N-酰亚胺离子的环化反应会生成3-乙烯基和3-乙炔基取代的吡咯烷和哌啶在结构上与脯氨酸和胡椒酸有关。
• Vicinal tricarbonyls in synthesis. New routes to indolizidines.
  作者：Harry H. Wasserman、Chi B. Vu、Jan D. Cook

  DOI：10.1016/s0040-4020(01)88877-3

  日期：——

  The vinyl vicinal tricarbonyl system 1 (VTC) has been used in two different approaches to prepare functionalized indolizidines. In one approach, 1 is used as a trielectrophile in reactions with primary amines possessing auxiliary donor sites. In a second approach, 1 is converted to a substituted 3-hydroxypyrrole-2-carboxylate. This pyrrole derivative then undergoes an intramolecular alkylation to give

  乙烯基邻位三羰基系统1（VTC）已用于两种不同的方法中，以制备功能化的吲哚并咪唑。在一种方法中，在与具有辅助供体位点的伯胺反应中，将1用作三亲电子试剂。在第二种方法中，将1转化为取代的3-羟基吡咯-2-羧酸酯。然后使该吡咯衍生物进行分子内烷基化，得到吲哚并立定环系统。
• The chemistry of vicinal tricarbonyls. New routes to indolizidines
  作者：Harry H. Wasserman、Jan D. Cook、Chi B. Vu

  DOI：10.1021/jo00293a005

  日期：1990.3
• Intramolecular reactions of acyclic N-acyliminium ions I propargyl silanes as nucleophiles
  作者：Henk Hiemstra、Hendrikus P. Fortgens、Sander Stegenga、W.Nico Speckamp

  DOI：10.1016/s0040-4039(00)98643-x

  日期：1985.1

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