1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1H-pyrrole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1H-pyrrole
• 英文别名: 1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1H-pyrrole；1-(2,3-dihydro-1,4-benzodioxin-6-yl)pyrrole
• 化学式: C₁₂H₁₁NO₂
• mdl: MFCD04070574
• 分子量: 201.225
• InChiKey: HMBOUQKESIRNCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  23.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1H-pyrrole 、 一氧化碳 在 氧气 、 copper(II) acetate monohydrate 、 palladium dichloride 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 24.0h， 以68%的产率得到
  参考文献：
  名称：

  Pd/Cu-catalyzed dual C–H bond carbonylation towards the synthesis of fluorazones

  摘要：

  Pd催化的氧化性双C-H键活化/羰基化仍然是一个巨大挑战，因为会生成副产物通过C-C键形成。在这里，我们开发了一种直接的Pd/Cu催化的氧化性双C-H键羰基化过程，从易得的N-芳基吡咯和CO利用O2作为末端氧化剂，制备生物学和药用重要的氟酮。

  DOI：

  10.1039/c7cc01707c
• 作为产物：
  描述：

  顺式-1,2-二羟甲基乙烯 、 6-氨基-1,4-苯并二氧杂环 在 2,2'-联吡啶 、 sodium carbonate 、 nickel dichloride 作用下， 以 甲苯 为溶剂， 反应 36.0h， 以85%的产率得到1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1H-pyrrole
  参考文献：
  名称：

  使用芳醇和烷基胺的二醇进行镍催化的N取代吡咯的合成

  摘要：

  在本文中，报道了使用具有一系列芳基，烷基和杂芳基胺的丁烯-1，4-二醇和丁炔1，4-二醇，镍催化的可持续合成N-取代的吡咯的策略。催化方案可耐受游离醇，卤化物，烷基，烷氧基，氧杂环，活化的苄基和吡啶部分，并能产生高达90％的收率。最初的机理研究涉及确定的镍催化剂，速率的确定和反应顺序，包括氘标记实验，用于吡咯合成。

  DOI：

  10.1021/acs.joc.8b02666

文献信息

• Synthesis and biological activity of new anti-inflammatory compounds containing the 1,4-benzodioxine and/or pyrrole system
  作者：Y. Harrak、G. Rosell、G. Daidone、S. Plescia、D. Schillaci、M.D. Pujol

  DOI：10.1016/j.bmc.2007.04.050

  日期：2007.7

  A series of substituted derivatives containing the 1,4-benzodioxine or pyrrole nucleus are described. All the newly synthesized compounds were examined for their in vitro and in vivo anti-inflammatory activity. Several derivatives, including (S)-2, 14 and 17, showed more anti-inflammatory activity in vivo in these assays (rat paw oedema induced by carrageenan) than the known classical anti-inflammatory agent ibuprofen, whereas other compounds like 1 were equipotent to ibuprofen. Compound 17 was the most outstanding derivative because of its remarkable in vivo anti-inflammatory activity. In this paper, we examine and discuss the structure-activity relationships and anti-inflammatory activities of these compounds. (c) 2007 Elsevier Ltd. All rights reserved.
• New strategy for the synthesis of N-aryl pyrroles: Cu-catalyzed C–N cross-coupling reaction of trans-4-hydroxy-l-proline with aryl halides
  作者：V. Prakash Reddy、A. Vijay Kumar、K. Rama Rao

  DOI：10.1016/j.tetlet.2010.12.016

  日期：2011.2

  trans-4-Hydroxy-L-proline is used for the first time as an effective nucleophilic coupling partner with aryl halides mediated by copper iodide with Cs(2)CO(3) as the base and DMSO as the solvent. Utilizing this protocol cross-coupling of trans-4-hydroxy-L-proline with a wide variety of substituted aryl halides to produce N-aryl pyrroles in moderate to good yields. (C) 2010 Elsevier Ltd. All rights reserved.
• An elegant protocol for the synthesis of N-substituted pyrroles through C–N cross coupling/aromatization process using CuFe2O4 nanoparticles as catalyst under ligand-free conditions
  作者：G. Satish、K. Harsha Vardhan Reddy、K. Ramesh、B.S.P. Anil Kumar、Y.V.D. Nageswar

  DOI：10.1016/j.tetlet.2014.01.075

  日期：2014.4

  A simple and efficient, ligand-free C-N cross-coupling of aryl halides/benzyl bromides with trans-4-hydroxy-L-proline has been developed to produce aromatized N-substituted pyrroles, using a catalytic amount of magnetically separable and recyclable CuFe2O4 nanoparticles, in the presence of Cs2CO3 in DMSO at 100 degrees C. (C) 2014 Elsevier Ltd. All rights reserved.
• Pd/Cu-catalyzed dual C–H bond carbonylation towards the synthesis of fluorazones
  作者：Fan Liao、Renyi Shi、Yuchen Sha、Jianhui Xia、Weilin Liao、Aiwen Lei

  DOI：10.1039/c7cc01707c

  日期：——

  Pd catalyzed oxidative dual C–H bond activation/carbonylation still remains a great challenge due to the generation of by-products via C–C bond formation. Herein, we developed a straightforward Pd/Cu-catalyzed oxidative dual C–H bond carbonylation process to access biologically and pharmaceutically important fluorazones from easily available N-aryl pyrroles and CO utilizing O₂ as the terminal oxidant.

  Pd催化的氧化性双C-H键活化/羰基化仍然是一个巨大挑战，因为会生成副产物通过C-C键形成。在这里，我们开发了一种直接的Pd/Cu催化的氧化性双C-H键羰基化过程，从易得的N-芳基吡咯和CO利用O2作为末端氧化剂，制备生物学和药用重要的氟酮。
• Nickel-Catalyzed Synthesis of <i>N</i>-Substituted Pyrroles Using Diols with Aryl- and Alkylamines
  作者：Khushboo Singh、Lalit Mohan Kabadwal、Sourajit Bera、Anitha Alanthadka、Debasis Banerjee

  DOI：10.1021/acs.joc.8b02666

  日期：2018.12.21

  Herein, nickel-catalyzed sustainable strategy for the synthesis of N-substituted pyrroles using butene-1,4-diols and butyne-1,4-diols with a series of aryl-, alkyl-, and heteroarylamines is reported. The catalytic protocol is tolerant of free alcohol, halide, alkyl, alkoxy, oxygen heterocycles, activated benzyl, and the pyridine moiety and resulted in up to 90% yield. Initial mechanistic studies involving

  在本文中，报道了使用具有一系列芳基，烷基和杂芳基胺的丁烯-1，4-二醇和丁炔1，4-二醇，镍催化的可持续合成N-取代的吡咯的策略。催化方案可耐受游离醇，卤化物，烷基，烷氧基，氧杂环，活化的苄基和吡啶部分，并能产生高达90％的收率。最初的机理研究涉及确定的镍催化剂，速率的确定和反应顺序，包括氘标记实验，用于吡咯合成。