8-甲基-2-苯基中氮茚 | 90456-28-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 8-甲基-2-苯基中氮茚
• 英文名称: 8-methyl-2-phenylindolizine
• CAS: 90456-28-3
• 化学式: C₁₅H₁₃N
• 分子量: 207.275
• InChiKey: XDRRRLVGEBOGBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  4.4
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  8-甲基-2-苯基中氮茚 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 15.0h， 生成 2-(8-Methyl-2-phenyl-indolizin-3-yl)-succinic acid dimethyl ester
  参考文献：
  名称：

  Yamashita, Yoshiro; Suzuki, Daisuke; Masumura, Mitsuo, Heterocycles, 1984, vol. 22, # 4, p. 705 - 708

  摘要：

  DOI：
• 作为产物：
  描述：

  苯乙酮 在 对甲苯磺酸 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 反应 34.17h， 生成 8-甲基-2-苯基中氮茚
  参考文献：
  名称：

  Oxidation Potential-Guided Electrochemical Radical–Radical Cross-Coupling Approaches to 3-Sulfonylated Imidazopyridines and Indolizines

  摘要：

  DOI：

  10.1021/acs.joc.1c00873

文献信息

• Ruthenium-NHC-Catalyzed Asymmetric Hydrogenation of Indolizines: Access to Indolizidine Alkaloids
  作者：Nuria Ortega、Dan-Tam D. Tang、Slawomir Urban、Dongbing Zhao、Frank Glorius

  DOI：10.1002/anie.201302218

  日期：2013.9.2

  complex serves as the catalyst for the high‐yielding and completely regioselective and asymmetric hydrogenation of substituted indolizines and 1,2,3‐triazolo‐[1,5‐a]pyridines. This method should provide ready access to bicyclic products bearing an N‐bridgehead, a motif appearing in 25–30 % of all naturally occurring alkaloids.

  越过N桥！钌/ N-杂环卡宾（NHC）络合物可作为取代吲哚嗪和1,2,3-三唑并[1,5- a ]吡啶的高产率，完全区域选择性和不对称氢化的催化剂。该方法应使带有N桥头的双环产物易于获得，该花环出现在所有天然生物碱的25％至30％中。
• Transition-Metal-Free Regioselective Cross-Coupling: Controlled Synthesis of Mono- or Dithiolation Indolizines
  作者：Bin Li、Zhiyu Chen、Hua Cao、Hong Zhao

  DOI：10.1021/acs.orglett.8b01168

  日期：2018.6.1

  indolizines with thiols has been developed for the first time to describe a workable route to indolizine thioethers. This finding provides a new method and more straightforward pathway for controllable synthesis of mono- or dithiolation indolizines that are otherwise difficult to obtain by the literature methods. The reaction exhibits good functional group tolerance and high efficiency and affords the products

  首次开发了一种有效的无过渡金属的吲哚嗪与硫醇的区域选择性C–H / S–H交叉偶联，以描述制备吲哚嗪硫醚的可行途径。这一发现为可控合成单硫醇或二硫醇化的吲哚嗪提供了新的方法和更直接的途径，否则文献方法很难获得。该反应表现出良好的官能团耐受性和高效率，并提供了良好至优异收率的产物。
• Regioselective C–H dithiocarbamation of indolizines with tetraalkylthiuram disulfide under metal-free conditions
  作者：Xiang Liu、Dan Song、Zemin Zhang、Jiatong Lin、Canzhan Zhuang、Haiying Zhan、Hua Cao

  DOI：10.1039/d1ob00701g

  日期：——

  disulfide has been described. A series of indolizine-dithiocarbamate derivatives were easily accessed in moderate to good yields with a broad scope. In addition, imidazo[1,2-a]pyridines were also well tolerated to afford diverse imidazoheterocycle-dithiocarbamate products, which are expected to be utilized for drug discovery. Of note, the reaction could be readily scaled up, and shows its practical value in

  已经描述了用四烷基秋兰姆二硫化物对中氮茚进行有效且直接的无金属区域选择性 C-H 二硫代氨基甲酸化。一系列中氮茚-二硫代氨基甲酸酯衍生物很容易以中等至良好的收率获得，范围广泛。此外，咪唑并[1,2 - a ]吡啶也具有良好的耐受性，可提供多种咪唑杂环-二硫代氨基甲酸酯产品，有望用于药物发现。值得注意的是，该反应可以很容易地放大，并显示出其在有机合成中的实用价值。
• Mechanochemical Synthesis of 1,2-Diketoindolizine Derivatives from Indolizines and Epoxides Using Piezoelectric Materials
  作者：Yumei Wang、Ziwu Zhang、Lichan Deng、Tianfeng Lao、Zhengquan Su、Yue Yu、Hua Cao

  DOI：10.1021/acs.orglett.1c02575

  日期：2021.9.17

  A simple and efficient mechanochemical-induced approach for the synthesis of 1,2-diketoindolizine derivatives has been developed. BaTiO3 was used as the piezoelectric material in this transformation. This method features no usage of solvent, simple experimental operation, scalable potential, and high conversion efficiency, which make it attractive and practical.

  已经开发了一种简单有效的机械化学诱导方法来合成 1,2-二酮吲哚嗪衍生物。BaTiO 3用作该转变中的压电材料。该方法不使用溶剂，实验操作简单，潜力可扩展，转化效率高，具有吸引力和实用性。
• Visible-Light-Induced Regioselective Dicarbonylation of Indolizines with Oxoaldehydes via Direct C–H Functionalization
  作者：Lili Teng、Xiang Liu、Pengfeng Guo、Yue Yu、Hua Cao

  DOI：10.1021/acs.orglett.0c01094

  日期：2020.5.15

  A metal-free system for regioselective dehydrogenative cross-couplings between indolizines and oxoaldehydes catalyzed by visible light under mild conditions has been described. As an atom economical and eco-friendly protocol, the reaction proceeds in good yields using inexpensive, readily available visible-light sources and the environmentally friendly oxidant oxygen. Various valuable 1,2-dicarbonyl

  已经描述了在温和条件下可见光催化的吲哚嗪和氧醛之间的区域选择性脱氢交叉偶联的无金属体系。作为一种原子经济且环保的方案，使用廉价，易于获得的可见光源和环境友好的氧化剂氧气，可以高产率进行反应。通过sp2 CH键的直接二羰基化，可以轻松获得与吲哚嗪核心相连的各种有价值的1,2-二羰基衍生物。