3-but-3-yn-1-yl-2-[(2-but-3-yn-1-ylnaphthalen-1-yl)ethynyl]pyridine | 1035428-65-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-but-3-yn-1-yl-2-[(2-but-3-yn-1-ylnaphthalen-1-yl)ethynyl]pyridine
• 英文别名: 3-But-3-ynyl-2-[2-(2-but-3-ynylnaphthalen-1-yl)ethynyl]pyridine；3-but-3-ynyl-2-[2-(2-but-3-ynylnaphthalen-1-yl)ethynyl]pyridine
• CAS: 1035428-65-9
• 化学式: C₂₅H₁₉N
• 分子量: 333.433
• InChiKey: XVNYUQVBDHGBRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-but-3-yn-1-yl-2-[(2-but-3-yn-1-ylnaphthalen-1-yl)ethynyl]pyridine 在 (-)-(S)-[2-(2-methoxynaphthalene-1-yl)phenyl]diphenylphosphine 、 bis(1,5-cyclooctadiene)nickel (0) 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以20%的产率得到5,6,9,10-tetrahydrobenzo[5,6]phenanthro[3,4-h]quinoline
  参考文献：
  名称：

  Chiral cobaltI and nickel0 complexes in the synthesis of nonracemic helicenes through the enantioselective [2 + 2 + 2] cyclotrimerisation of alkynes

  摘要：

  The enantioselective intramolecular [2 + 2 + 2] cycloisomerisation of triynes under catalysis by chiral transition-metal complexes (Co-I, Ni-0) in order to receive nonracemic helicene derivatives was explored. The use of the chiral neomenthylindene Co-I complex led to a moderate 25% ee of tetrahydro[6] helicene, which was the first example of such a reaction catalysed by the chiral Co-I complex. The alternative Ni-0 catalysis employing privileged axially chiral monophosphines such as (-)-(aS)-NAPHEP led to tetrahydro [6] helicene with 64% ee, which is among the highest enantiomeric excesses so far observed for this Ni-0-catalysed reaction. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.07.005
• 作为产物：
  描述：

  3-{4-[三(1-甲基乙基)甲硅烷基]丁-3-炔-1-基}-2-[(2-{4-[三(1-甲基乙基)甲硅烷基]丁-3-炔-1-基}萘-1-基)乙炔基]吡啶 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 30.0h， 以92%的产率得到3-but-3-yn-1-yl-2-[(2-but-3-yn-1-ylnaphthalen-1-yl)ethynyl]pyridine
  参考文献：
  名称：

  螺旋手性N-杂芳族化合物的直接途径：外消旋1,14-二氮杂[5]螺旋烯和光学纯的1-和2-氮杂[6]螺旋烯的实际合成。

  摘要：

  DOI：

  10.1002/anie.200705463

文献信息

• Enantioselective [2+2+2] cycloisomerisation of alkynes in the synthesis of helicenes: The search for effective chiral ligands
  作者：Irena G. Stará、Angelina Andronova、Adrian Kollárovič、Štěpán Vyskočil、Sylvain Jugé、Guy C. Lloyd-Jones、Patrick J. Guiry、Ivo Starý

  DOI：10.1135/cccc2011177

  日期：——

  The enantioselective [2+2+2] cycloisomerisation of the aromatic triynes under nickel(0) catalysis to afford nonracemic [6]- and [7]helicene derivatives has been systematically studied. A collection of mono- and bidentate phosphines, phosphites, phosphinites and phosphinous amides possessing stereogenic units such as chiral centre, axis or plane (or their combinations) has been tested and axially chiral binaphthyl-derived monodentate MOP-type phosphine ligands were the optimal class of ligands. Nickel complexes of these ligands afforded nonracemic tetrahydro[6]helicene in up to 64% ee in a model reaction.

  芳香族三炔烃在镍（0）催化下进行立体选择性的[2+2+2]环异构化反应，生成非拉克米的[6]-和[7]螺芴衍生物已经被系统研究。一系列具有手性中心、轴或平面（或它们的组合）的单齿和双齿膦、膦酸酯、膦酸酯和膦酰胺已经被测试，其中轴手性的双齿MOP型膦配体是最佳的配体类别。这些配体的镍配合物在模型反应中生成非拉克米的四氢[6]螺芴，其对映选择性可高达64% ee。
• Misek, Jiri; Tichy, Milos; Stara, Irena G., Croatica Chemica Acta, 2009, vol. 82, # 1, p. 79 - 86
  作者：Misek, Jiri、Tichy, Milos、Stara, Irena G.、Stary, Ivo、Roithova, Jana、Schroeder, Detlef

  DOI：——

  日期：——