2-(吡啶-2-基)-4-(噻吩-3-基)丁-3-炔-2-醇 | 1046337-92-1

• 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
• 中文名称: 2-(吡啶-2-基)-4-(噻吩-3-基)丁-3-炔-2-醇
• 英文名称: 2-(pyridin-2-yl)-4-(thiophen-3-yl)but-3-yn-2-ol
• 英文别名: 2-Pyridin-2-yl-4-thiophen-3-ylbut-3-yn-2-ol
• CAS: 1046337-92-1
• 化学式: C₁₃H₁₁NOS
• 分子量: 229.302
• InChiKey: MRRGGPDYDJWAOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  61.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(吡啶-2-基)-4-(噻吩-3-基)丁-3-炔-2-醇 在 碘 、 caesium carbonate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 6.0h， 生成 2-Iodo-8a-methyl-3-thiophen-3-ylindolizin-1-one
  参考文献：
  名称：

  Diversity-Oriented Construction of Highly Substituted Indolizinones

  摘要：

  Rapid generation of small library of highly functionalized indolizonones was realized by exploiting three palladium-catalyzed cross-coupling reactions of 2-iodoindolizinones which in turn were readily accessed via sequential iodine-mediated cyclization/1,2-shift reactions of propargylic alcohols.

  DOI：

  10.1021/cc100015k
• 作为产物：
  描述：

  2-乙酰基吡啶 、 3-thiopheneethynyllithium 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.33h， 生成 2-(吡啶-2-基)-4-(噻吩-3-基)丁-3-炔-2-醇
  参考文献：
  名称：

  Diversity-Oriented Construction of Highly Substituted Indolizinones

  摘要：

  Rapid generation of small library of highly functionalized indolizonones was realized by exploiting three palladium-catalyzed cross-coupling reactions of 2-iodoindolizinones which in turn were readily accessed via sequential iodine-mediated cyclization/1,2-shift reactions of propargylic alcohols.

  DOI：

  10.1021/cc100015k

文献信息

• Efficient Synthesis of Highly Substituted Indolizinones via Iodocyclization and 1,2-Shift
  作者：Ikyon Kim、Jihyun Choi、Ge Hyeong Lee

  DOI：10.1055/s-2008-1072721

  日期：2008.5

  The 5-endo-dig iodocyclization of propargylic alcohols followed by a 1,2-shift provided rapid access to 2-iodoindolizinones, while the 5-endo-trig iodocyclization of allylic alcohols and subsequent dehydroiodination and 1,2-shift led to indolizinones. A number of highly substituted indolizinones were constructed under these mild reaction conditions.

  炔丙醇的 5-内二位碘环化和随后的 1,2-转变提供了快速获得 2-碘吲嗪酮的途径，而烯丙醇的 5-内三碘环化以及随后的脱氢碘化和 1,2-转变产生了吲哚嗪酮。在这些温和的反应条件下构建了许多高度取代的中氮茚酮。
• Synthesis and study of Au(<scp>iii</scp>)–indolizine derivatives: turn-on luminescence by photo-induced controlled release
  作者：Jie Yang、Yifan Zhu、Anfernee Kai-Wing Tse、Xinghua Zhou、Yang Chen、Yu Chung Tse、Keith Man-Chung Wong、Chun-Yu Ho

  DOI：10.1039/c8cc10177a

  日期：——

  The photo- and structural properties of a series of Au(III) indolizine complexes were determined. Controlled release of halogenated indolizine derivatives from the corresponding Au(III) complexes was achieved by photoinduced C–X bond formation, which provided turn-on luminescence with an increase in emission intensity of up to 67 times.

  测定了一系列Au（III）吲哚嗪复合物的光和结构性质。通过光诱导的C–X键的形成，可以控制卤素从相应的Au（III）配合物中释放出来的吲哚嗪衍生物，从而提供了开启发光功能，其发光强度增加了67倍。
• A Highly Efficient Catalyst-Free Cycloisomerization Approach to Indolizinones
  作者：Ikyon Kim、Jihyun Choi、Sunkyung Lee、Ge Lee

  DOI：10.1055/s-2008-1078022

  日期：——

  A highly efficient catalyst-free synthetic route to indoli­zinones was established from readily available tertiary propargylic alcohols via a facile thermally induced cycloisomerization. In addition, this transformation was found to be further expedited by microwave irradiation.

  以易得的叔炔醇为原料，通过简单的热诱导环异构化，建立了一种高效的无催化剂合成吲哚嗪酮的路线。此外，还发现微波辐射进一步加速了这种转变。
• Palladium-catalyzed construction of poly-substituted indolizinones
  作者：Hanyang Cho、Ikyon Kim

  DOI：10.1016/j.tet.2012.04.091

  日期：2012.7

  We have developed a highly efficient one-pot approach to poly-substituted indolizinones from tertiary propargylic alcohols by using a palladium-catalyzed domino reaction. This reaction is proposed to proceed via successive aminopalladation, reductive elimination, and 1,2-shift. While our previous effort to the same skeleton via 2-iodoindolizinones selected alpha,beta-unsaturated esters, terminal acetylenes, or boronic acids as coupling partners, this strategy introduces new functional groups at the C2 position of indolizinone core with (hetero)aryl halides or diallyl carbonate, expanding the substrate scope for decoration at the C2 site. Furthermore, a new preparation route to tertiary propargylic alcohols for this study is described to rapidly diversify the molecular framework. (c) 2012 Elsevier Ltd. All rights reserved.
• Expeditious Synthesis of Highly Substituted Indolizinones via a Palladium-Catalyzed Domino Sequence
  作者：Ikyon Kim、Kyungsun Kim

  DOI：10.1021/ol1006778

  日期：2010.6.4

  A direct one-pot approach to polysubstituted indolizinones from tertiary propargylic alcohols using a palladium-catalyzed domino process involving aminopalladation, reductive elimination, and 1,2-shift is described.