diethyl indolizine-1,3-dicarboxylate | 55814-13-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: diethyl indolizine-1,3-dicarboxylate
• CAS: 55814-13-6
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: XPEJYNHPQYHYAT-UHFFFAOYSA-N

物化性质

• 熔点：
  130-131 °C(Solv: ligroine (8032-32-4))
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (1Z,3E)-1,5-diethoxy-2-ethoxycarbonyl-5-oxo-4-pyridin-1-ium-1-ylpenta-1,3-dien-1-olate 以25%的产率得到
  参考文献：
  名称：

  TAMURA Y.; SUMIDA Y.; HARUKI S.; IKEDA M., J. CHEM. SOC. PERKIN TRANS. , 1975, PART 1, NO 6, 575-579

  摘要：

  DOI：

文献信息

• Iron-Catalyzed Indolizine Synthesis from Pyridines, Diazo Compounds, and Alkynes
  作者：Tim Douglas、Anca Pordea、James Dowden

  DOI：10.1021/acs.orglett.7b03252

  日期：2017.12.1

  The iron(III)-catalyzed synthesis of indolizines from commercially available alkyne, pyridine, and diazo precursors is reported. This mild, expedient method is tolerant of various solvents and proceeds with as little as 0.25 mol % [Fe(TPP)Cl]. Significantly, this multicomponent reaction is compatible with electrophilic alkynes; control experiments demonstrate the importance of the catalyst in promoting

  据报道，铁（III）由市售的炔烃，吡啶和重氮前体合成了吲哚嗪。这种温和，简便的方法可耐受各种溶剂，并且只需低至0.25 mol％的[Fe（TPP）Cl]即可进行。值得注意的是，这种多组分反应与亲电炔烃相容。对照实验证明了催化剂在促进吡啶鎓叶立德形成中的重要性超过背景反应性。
• Iodine Mediated Base‐Controlled Regio‐Selective Annulation of 2‐(Pyridin‐2‐yl)acetate Derivatives with Acrylic Esters for the Synthesis of Indolizines
  作者：Youlai Fang、Fei Li、Yuzhu Yang、Xiaolan Liu、Weidong Pan

  DOI：10.1002/adsc.202000103

  日期：2020.3.17

  An iodine mediated base‐controlled reaction between 2‐(pyridin‐2‐yl)acetate derivatives and acrylic esters has been developed for the selective synthesis of 1,3‐disubstituted indolizines and 1,2‐disubstituted indolizines. A single‐pot reaction of 2‐(pyridin‐2‐yl)acetate derivatives and acrylic esters in the presence of CsOAc delivers 1,3‐disubstitued indolizines, while KHCO3 promotes the formation

  已经开发出碘介导的2-吡啶（2-吡啶基）乙酸酯衍生物与丙烯酸酯之间的碱控制反应，用于选择性合成1,3-二取代的吲哚嗪和1,2-二取代的吲哚嗪。在存在CsOAc的情况下，2-（吡啶-2-基）乙酸酯衍生物和丙烯酸酯的单锅反应可生成1,3-二取代的吲哚嗪，而KHCO 3促进C3-碘吲哚的生成，这可能进一步被破坏。在铜粉存在下碘化，通过连续的逐步方式得到1,2-二取代的吲哚嗪。对于该反应，已经提出了涉及自由基过程的合理的反应机理。已经描述了C3-碘吲哚嗪与芳基硼酸的钯催化过氧化反应。
• Hemoglobin-Catalyzed Synthesis of Indolizines Under Mild Conditions
  作者：Fengxi Li、Xuyong Tang、Yaning Xu、Chunyu Wang、Liu Zhang、Jiaxin Zhang、Jiaxu Liu、Zhengqiang Li、Lei Wang

  DOI：10.1002/ejoc.201901591

  日期：2019.12.19

  Hemoglobins were used to catalyze the multicomponent synthesis of indolizines. Satisfactory yields and mild reaction conditions make this method highly useful for practical applications. Furthermore, this study provides a new example of a hemoglobin‐catalyzed organic reaction and is expected to expand the utilization of hemoglobin in organic synthesis.

  血红蛋白被用来催化吲哚嗪的多组分合成。令人满意的收率和温和的反应条件使该方法在实际应用中非常有用。此外，这项研究提供了血红蛋白催化的有机反应的新实例，并有望扩大血红蛋白在有机合成中的利用。
• Copper-catalyzed formal [1 + 2 + 2]-annulation of alkyne-tethered diazoacetates and pyridines: access to polycyclic indolizines
  作者：Shanliang Dong、Jingjing Huang、Hongkai Sha、Lihua Qiu、Wenhao Hu、Xinfang Xu

  DOI：10.1039/d0ob00222d

  日期：——

  A copper-catalyzed formal [1 + 2 + 2]-annulation of alkyne-tethered diazo compounds with pyridines, which affords polycyclic fused indolizines in synthetically useful to good yields under mild reaction conditions, has been reported. This method features the use of an inexpensive copper catalyst and readily available starting materials, broad substrate generality, and operational simplicity. Notably

  据报导，铜连接的炔烃系重氮化合物与吡啶的正式[1 + 2 + 2]环化反应，可在温和的反应条件下提供多环稠合的吲哚并嗪，可合成用于高产。该方法的特点是使用廉价的铜催化剂和易于获得的起始原料，广泛的底物通用性和操作简便性。值得注意的是，多种天然产物衍生物在当前条件下是相容的，这表明该方法用于选择性修饰和修饰类似生物分子或药物的巨大潜力。
• Iodine-Mediated Oxidative Cyclization of 2-(Pyridin-2-yl)acetate Derivatives with Alkynes: Condition-Controlled Selective Synthesis of Multisubstituted Indolizines
  作者：Lisheng He、Yuzhu Yang、Xiaolan Liu、Guangyan Liang、Chunyan Li、Daoping Wang、Weidong Pan

  DOI：10.1055/s-0039-1690229

  日期：2020.2

  An iodine-mediated oxidative cyclization reaction between 2-(pyridin-2-yl)acetate derivatives and different alkynes has been developed, which provides regioselective and chemoselective syntheses of multiply substituted indolizines under modified reaction conditions. Plausible mechanisms have been proposed to explain the selective syntheses of indolizines. This protocol can be also applied to the stepwise

  已经开发出碘介导的2-（吡啶-2-基）乙酸酯衍生物与不同炔烃之间的碘介导的氧化环化反应，该反应在修饰的反应条件下提供了多重取代的吲哚嗪的区域选择性和化学选择性合成。已经提出了合理的机制来解释吲哚嗪的选择性合成。该方案也可以应用于2,2'-联吲哚并逐步合成。