3-phenyl-1-(2-pyridinyl)-2-propynyl acetate | 949101-24-0

• 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: 3-phenyl-1-(2-pyridinyl)-2-propynyl acetate
• 英文别名: acetic acid 3-phenyl-1-(pyridin-2-yl)prop-2-ynyl ester；3-phenyl-1-(pyridin-2-yl)prop-2-yn-1-yl acetate；3-phenyl-1-(pyridin-2-yl)prop-2-ynyl acetate；(3-Phenyl-1-pyridin-2-ylprop-2-ynyl) acetate
• CAS: 949101-24-0
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: WLFTUPABEPLJBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-phenyl-1-(2-pyridinyl)-2-propynyl acetate 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以95%的产率得到(2-Iodo-3-phenylindolizin-1-yl) acetate
  参考文献：
  名称：

  通过碘氮茚衍生物的合成迅速介导的5-内切-挖环化

  摘要：

  碘介导的5-内切-挖炔丙基酯的环化2在室温下顺利进行，得到高度官能化氮茚3以优良产率。在该简便方法中，吡啶基团首次被用作亲核伴侣。

  DOI：

  10.1016/j.tetlet.2007.07.180
• 作为产物：
  描述：

  苯乙炔 在 4-二甲氨基吡啶 、 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 37.67h， 生成 3-phenyl-1-(2-pyridinyl)-2-propynyl acetate
  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

文献信息

• Multisubstituted N-fused heterocycles via transition metal-catalyzed cycloisomerization protocols
  作者：Ilya V. Seregin、Alex W. Schammel、Vladimir Gevorgyan

  DOI：10.1016/j.tet.2008.04.023

  日期：2008.7

  multisubstituted N-fused heterocycles have been developed. It was demonstrated that 1,3-disubstituted N-fused heterocycles, including indolizines, pyrroloquinoxalines, and pyrrolothiazoles can easily be synthesized via an exceptionally mild and efficient method involving a novel silver-catalyzed cycloizomerization of propargyl-containing heterocycles. Alternatively, 1,2-disubstituted heterocycles can be accessed

  已经开发了两种用于组装多取代 N-稠合杂环的互补方案。结果表明，1,3-二取代的 N-稠合杂环，包括中氮茚、吡咯并喹喔啉和吡咯并噻唑，可以通过一种极其温和且有效的方法轻松合成，该方法涉及新型银催化含炔丙基杂环的环化聚合。或者，可以通过涉及炔烃-亚乙烯基异构化以及伴随的氢、甲硅烷基、甲锡烷基或甲锗烷基基团的1,2-位移的新型级联转化来获得1,2-二取代的杂环。这种温和而简单的方法可以选择性且高效地合成中氮茚、吡咯并异喹啉、吡咯并喹喔啉、吡咯并吡嗪和吡咯并噻唑。
• Copper-Catalyzed Carbon-Nitrogen/Carbon-Selenium Bonds Formation: Synthesis of 2-(Organochalcogenyl)-indolizines
  作者：Tales A. C. Goulart、Davi F. Back、Gilson Zeni

  DOI：10.1002/adsc.201700166

  日期：2017.6.6

  standard reaction conditions were compatible with many functional groups in the substrates, such as methyl, chlorine, fluorine, methoxy and trifluoromethyl. This protocol was efficient with diorganyl diselenides and ditellurides but ineffective with diorganyl disulfides. In addition, the obtained 2‐(organochalcogenyl)‐indolizines were readily transformed into more complex products by reaction with boronic

  铜催化的炔丙基吡啶与二有机基二硫代双氰化物的环化反应被用于合成2-（有机锡烷基）吲哚并嗪。对环化系统的系统研究表明，碘化铜（I）与二有机基二卤代双金属间的相互作用对于形成高产率的吲哚嗪来说至关重要，可避免形成氢化的吲哚嗪。标准反应条件与底物中的许多官能团相容，例如甲基，氯，氟，甲氧基和三氟甲基。该方案对二有机基二硒化物和二碲化物有效，但对二有机基二硫化物无效。此外，
• Synthesis of Indolizine Derivatives Triggered by the Oxidative Addition of Aroyl Chloride to Pd(0) Complex
  作者：Yahui Li、Wei Xiong、Zhifeng Zhang、Tongyu Xu

  DOI：10.1021/acs.joc.0c00161

  日期：2020.5.15

  An efficient synthesis of indolizine derivatives from propargylic pyridines and aroyl chlorides was developed. The 5-endo-dig cyclization was initiated by the in situ formed acylpalladium species from the facile oxidative addition of aroyl chloride to Pd(0) complex. This transformation successfully occurred in the presence of an N-nucleophilic moiety and acid chlorides, a good electrophilic partner

  从炔丙基吡啶和芳酰氯有效地合成了吲哚嗪衍生物。5-endo-dig环化反应是由就地形成的酰基铝化合物从芳酰氯向Pd（0）络合物的容易氧化加成开始的。在N-亲核基团和酰基氯（一种良好的亲电伙伴）的存在下成功进行了该转化，从而以良好至优异的产率提供了高度官能化的吲哚嗪。
• Palladium-Catalyzed Difunctionalization of Alkenes by Relay Coupling with Propargylic Pyridines: Synthesis of Indolizine and Indolizinone-Containing Bisheterocycles
  作者：Xiao Xiao、Puren Han、Huiwen Zhou、Jianchao Liu

  DOI：10.1021/acs.joc.1c02438

  日期：2021.12.17

  Palladium-catalyzed arylation/heteroarylation of aryl halide-tethered alkenes with propargylic pyridines has been established, which provides direct and efficient access to various oxindole, azaoxindole, dihydrobenzopyran, indole, and benzofuran-linked indolizines in good yields with a broad substrate scope and high functional group tolerance. This process enables the formation of one C–N and two C–C

  已经建立了钯催化的芳基卤化物连接的烯烃与炔丙基吡啶的芳基化/杂芳基化，可以直接有效地获得各种羟吲哚、氮杂吲哚、二氢苯并吡喃、吲哚和苯并呋喃连接的吲哚腙，收率高，底物范围广，高官能团耐受性。该过程能够通过分子内碳钯化和环异构化序列在一次操作中形成一个 C-N 键和两个 C-C 键。此外，包含吲哚和苯并呋喃的吲哚嗪酮连接的双杂环骨架可以从​​涉及甲基或苯基迁移的叔炔醇中方便地合成。
• Synthesis of Indolizine Derivatives by Pd-Catalyzed Oxidative Carbonylation
  作者：Tongyu Xu、Howard Alper

  DOI：10.1021/acs.orglett.5b02220

  日期：2015.9.18

  An efficient synthesis of indolizine derivatives by palladium-catalyzed oxidative carbonylation of propargylic pyridines has been developed. The reaction can be conducted at room temperature and under 3 bar of CO in the presence of Pd2(dba)3 or Pd/C. The catalyst Pd/C could be easily removed from the reaction and recycled.

  已经开发了通过钯催化的炔丙基吡啶的氧化羰基化来有效合成吲哚嗪衍生物。该反应可以在室温下和在3巴的CO下，在Pd 2（dba）3或Pd / C存在下进行。催化剂Pd / C可以容易地从反应中除去并再循环。