2-ethynyl-6-(phenylmethoxy)pyridine | 134080-69-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-ethynyl-6-(phenylmethoxy)pyridine
• 英文别名: 2-(Benzyloxy)-6-ethynylpyridine；2-benzyloxy-6-ethynyl pyridine；6-Benzyloxy-2-ethynylpyridine；2-ethynyl-6-phenylmethoxypyridine
• CAS: 134080-69-6
• 化学式: C₁₄H₁₁NO
• 分子量: 209.247
• InChiKey: RFYOPNSZHGZQTI-UHFFFAOYSA-N

物化性质

• 沸点：
  338.7±32.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-ethynyl-6-(phenylmethoxy)pyridine 在 Lindlar's catalyst 、 镍 氢气 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (1R,2S,5R,8S,9S)-2-hydroxy-10-methyl-6,10-diazatetracyclo[7.2.2.25,8.01,5]pentadeca-12,14-diene-7,11-dione
  参考文献：
  名称：

  Sieburth, Scott Mc.N.; Chen, Jian-Long, Journal of the American Chemical Society, 1991, vol. 113, # 21, p. 8163 - 8164

  摘要：

  DOI：
• 作为产物：
  描述：

  2,6-二溴吡啶 在 palladium diacetate 、 氢氧化钾 、 copper(l) iodide 、 二乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-ethynyl-6-(phenylmethoxy)pyridine
  参考文献：
  名称：

  Sieburth, Scott Mc.N.; Chen, Jian-Long, Journal of the American Chemical Society, 1991, vol. 113, # 21, p. 8163 - 8164

  摘要：

  DOI：

文献信息

• Fusicoccin Synthesis by Intramolecular [4+4] Photocycloaddition of 2-Pyridones: Stereocontrol of the Cycloaddition and Elaboration of the Pentacyclic Product
  作者：Kevin McGee、Taleb Al-Tel、Scott Sieburth

  DOI：10.1055/s-2001-15066

  日期：——

  Intramolecular photocycloaddition of a three-carbon tethered pyrindinone–pyridone system yields the 5-8-5 ring system of the fusicoccin/ophiobolin/ceroplastol families. The stereoselectivity of the cycloaddition was found to be dependent on nitrogen substitution; N-methylation led to exclusively trans products while an absence of nitrogen substitution resulted in solvent-dependent stereoselectivity

  三碳束缚吡啶酮-吡啶酮系统的分子内光环加成产生了 fusicoccin/ophiobolin/ceroplastol 家族的 5-8-5 环系统。发现环加成的立体选择性取决于氮取代；N-甲基化仅导致反式产物，而没有氮取代导致溶剂依赖性立体选择性。这种环加成的溶剂和浓度效应与在非极性溶剂和更高浓度下强制形成顺式构象的氢键二聚体一致。顺式异构体，一种褐藻素合成中间体，在环境温度下经历了 Cope 重排，但可以作为单环氧化物有效地被捕获，产生具有六个新立体中心的产物。
• Fusicoccin ring system by [4+4] cycloaddition. 2. A model study
  作者：Scott McN. Sieburth、Kevin F. McGee、Taleb H. Al-Tel

  DOI：10.1016/s0040-4039(99)00671-1

  日期：1999.5

  A synthetic approach to fusicoccin A utilizing intramolecular photocycloaddition of tethered 2-pyridones has been completed. This study has led to the first solvent-dependent 2-pyridone photo-cycloaddition yielding either cis or trans products. Epoxidation of the cis photoproduct is selective for the disubstituted alkene, stabilizes the product, and is properly located for installation of the trans-1

  已经完成了利用束缚的2-吡啶酮的分子内光环加成法合成呋喃西星A的方法。这项研究导致了第一个溶剂依赖性的2-吡啶酮光环加成反应，产生顺式或反式产物。顺式光产物的环氧化对双取代的烯烃具有选择性，使产物稳定，并适合安装反式1，2-二醇。通过与异氰酸酯反应活化仲酰胺导致新戊酰胺羰基还原为甲基。
• Self-Assembled Dinuclear Cobalt(II)-Salen Catalyst Through Hydrogen-Bonding and Its Application to Enantioselective Nitro-Aldol (Henry) Reaction
  作者：Jongwoo Park、Kai Lang、Khalil A. Abboud、Sukwon Hong

  DOI：10.1021/ja807221s

  日期：2008.12.10

  Novel chiral dinuclear Co(II)-salen catalysts self-assembled through the pyridone/aminopyridine hydrogen-bonding pair have been developed. The self-assembled dinuclear Co(II)-Salen catalyst results in significant rate acceleration (48 times faster rate) as well, as excellent enantioselectivity (96% ee vs 55% ee) in a nitro-aldol reaction, compared to the corresponding monomeric catalyst. A bimetallic mechanism is suggested by the kinetic experiment showing that the rate taw is second order in [catalyst]. The self-assembly through hydrogen bonding was confirmed by X-ray structure and by the H-1 experiments revealing that the dimerization constant of the novel hydrogen-bonding capable salen (ligand in 25% v/v CD3NO2/CDCl3 is 53 +/- 21 M-1. This result proves the validity of self-assembly based approaches toward the efficient construction of chiral bimetallic catalyst system.
• Hydrogen bonding interaction of CpCo(Dithiolene) complex with monocyclic 2-pyridonyl substituent and unexpected formation of dithiolene-fused tricyclic pyridone derivative
  作者：Mitsushiro Nomura、Mami Kanamori、Yoshino Yamaguchi、Naoki Tateno、Chikako Fujita-Takayama、Toru Sugiyama、Masatsugu Kajitani

  DOI：10.1016/j.jorganchem.2009.04.022

  日期：2009.8

  One-pot reaction of [CpCo(CO)(2)], elemental sulfur with some heterocycle-substituted alkynes (R-C C-HET) produced [CpCo(dithiolene)] complexes with (PyOBn)-Py-2 (2), with both (PyOBn)-Py-2 and 2-hydroxy-2-propyl groups (C(OH)Me-2) (5), both Py-2 and C(OH)Me-2 (8), both Py-4 and C(OH)Me-2 (11), and with Py-4 substituent (13). A deprotection of benzyl group (Bn) from 2 with trimethylsilyl iodide formed [CpCo(dithiolene)] with 2-pyridonyl substituent (3). Heating reaction of 8 without any base resulted in the C(OH)Me-2 group elimination to form the 2-pyridylethylenedithiolate complex (9), but 11 underwent only dehydration at the C(OH)Me-2 under heating. While the preparation of 5, the benzyl free complex (6) was obtained as a main product. 6 has a dithiolene-fused tricyclic pyridone skeleton. The structures of 3, 5, 6, 8, and 11 were determined by X-ray diffraction studies. Intramolecular OH center dot center dot center dot N(Py-2) hydrogen bondings are found in 5 and 8, and an intermolecular OH center dot center dot center dot N(Py-4) one is found in 11 at solid state. In the 2-pyridonyl complex 3, intermolecular NH center dot center dot center dot O and CH(dithiolene)center dot center dot center dot O hydrogen bondings are observed. 8 showed an intermolecular Cp center dot center dot center dot Cp face-to-face interaction. The tricyclic complex 6 exhibited lower energy electronic absorption (lambda(max) = 668 nm) compared with the others (lambda(max) = 562-614 nm), due to an extended pi-conjugation of aromatic cobaltadithiolene ring. (C) 2009 Elsevier B.V. All rights reserved.
• Use of Hydrogen Bonds to Control Molecular Aggregation. Behavior of Dipyridones and Pyridone-Pyrimidones Designed To Form Cyclic Triplexes
  作者：Eric Boucher、Michel Simard、James D. Wuest

  DOI：10.1021/jo00110a050

  日期：1995.3

  The tendency of 2-pyridones and related heterocycles to form cyclic hydrogen-bonded dimers allows them to be used as sticky sites that induce molecules in which they are incorporated to associate in particular ways. Compound 7, which is constructed from pyridone and pyrimidone subunits linked to a rigid linear acetylenic spacer, incorporates an array of hydrogen-bonding sites designed to favor the formation of a cyclic tripler. Pyridone-pyrimidone 7 was synthesized and the structure of its DMSO solvate was determined by X-ray crystallography. Aggregation does not produce a cyclic tripler but rather gives chains in which adjacent molecules of compound 7 are linked by single hydrogen bonds.