1-phenyl-1-(pyridin-2-yl)hept-2-yn-1-ol | 36300-58-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-phenyl-1-(pyridin-2-yl)hept-2-yn-1-ol
• 英文别名: 1-Phenyl-1-pyridin-2-ylhept-2-yn-1-ol；1-phenyl-1-pyridin-2-ylhept-2-yn-1-ol
• CAS: 36300-58-0
• 化学式: C₁₈H₁₉NO
• 分子量: 265.355
• InChiKey: LTNJEJZVPONJTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-phenyl-1-(pyridin-2-yl)hept-2-yn-1-ol 在 4-二甲氨基吡啶 、 碘 、 copper(l) cyanide 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 、 正戊烷 为溶剂， 反应 98.42h， 生成 3-butyl-2-iodo-1-phenylindolizine
  参考文献：
  名称：

  Straightforward Access to 2-Iodoindolizines via Iodine-Mediated Cyclization of 2-Pyridylallenes

  摘要：

  A metal-free access to 2-iodo-1,3-disubstituted indolizines has been developed. The proposed synthesis is relatively simple and efficient and involves the iodine-triggered 5-endo-trig cyclization of 2-pyridylallene precursors. While it can be conducted on a gram scale, the preparation of the precursors is straightforward and does not always require intermediate purifications. The obtained 2-iodoindolizines can be further functionalized through cross-coupling reactions.

  DOI：

  10.1021/acs.oprd.9b00418
• 作为产物：
  描述：

  2-苯甲酰吡啶 、 1-己炔 在 乙基溴化镁 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以85%的产率得到1-phenyl-1-(pyridin-2-yl)hept-2-yn-1-ol
  参考文献：
  名称：

  Pt-Catalyzed Cyclization/1,2-Migration for the Synthesis of Indolizines, Pyrrolones, and Indolizinones

  摘要：

  Indolizine, pyrrolone, and indolizinone heterocycles are easily accessed via the Pt(II)-catalyzed cycloisomerization or a tandem cyclization/1,2-migration of pyridine propargylic alcohols and derivatives. This method provides an efficient synthesis of highly functionalized heterocycles from readily available substrates.

  DOI：

  10.1021/ol0701971

文献信息

• Pt-Catalyzed Cyclization/1,2-Migration for the Synthesis of Indolizines, Pyrrolones, and Indolizinones
  作者：Cameron R. Smith、Eric M. Bunnelle、Allison J. Rhodes、Richmond Sarpong

  DOI：10.1021/ol0701971

  日期：2007.3.1

  Indolizine, pyrrolone, and indolizinone heterocycles are easily accessed via the Pt(II)-catalyzed cycloisomerization or a tandem cyclization/1,2-migration of pyridine propargylic alcohols and derivatives. This method provides an efficient synthesis of highly functionalized heterocycles from readily available substrates.
• Highly Efficient Synthesis of Functionalized Indolizines and Indolizinones by Copper-Catalyzed Cycloisomerizations of Propargylic Pyridines
  作者：Bin Yan、Yebing Zhou、Hao Zhang、Jingjin Chen、Yuanhong Liu

  DOI：10.1021/jo070983j

  日期：2007.9.1

  [GRAPHICS]The copper-catalyzed cycloisomerizations of 2-pyridyl-substituted propargylic acetates and its derivatives are described, which offer an efficient route to C-1 oxygenated indolizines with a wide range of substituents under mild reaction conditions. The presented method could be readily applied to the synthesis of indolizinones through a cyclization/1,2-migration of tertiary propargylic alcohols.
• Pt-catalyzed cyclization/migration of propargylic alcohols for the synthesis of 3(2H)-furanones, pyrrolones, indolizines, and indolizinones
  作者：Eric M. Bunnelle、Cameron R. Smith、Sharon K. Lee、Surendra W. Singaram、Allison J. Rhodes、Richmond Sarpong

  DOI：10.1016/j.tet.2008.02.103

  日期：2008.7

  Several heterocycles such as furanones, pyrrolones, and indolizines, which are of pharmacological importance, are easily accessed via the Pt(II)-catalyzed heterocyclization/1,2-migration of propargylic ketols or hydroxy imine derivatives. This method sidesteps the challenges of traditional heteroaromatic oxygenation strategies such as regioselectivity and functional group tolerance in the syntheses of these heterocycles. (C) 2008 Elsevier Ltd. All rights reserved.
• Straightforward Access to 2-Iodoindolizines via Iodine-Mediated Cyclization of 2-Pyridylallenes
  作者：Thibaut Martinez、Ismail Alahyen、Gilles Lemière、Virginie Mouriès-Mansuy、Louis Fensterbank

  DOI：10.1021/acs.oprd.9b00418

  日期：2020.5.15

  A metal-free access to 2-iodo-1,3-disubstituted indolizines has been developed. The proposed synthesis is relatively simple and efficient and involves the iodine-triggered 5-endo-trig cyclization of 2-pyridylallene precursors. While it can be conducted on a gram scale, the preparation of the precursors is straightforward and does not always require intermediate purifications. The obtained 2-iodoindolizines can be further functionalized through cross-coupling reactions.