1-(benzo[d][1,3]dioxol-5-yl)-1H-pyrrole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 1-(benzo[d][1,3]dioxol-5-yl)-1H-pyrrole
• 英文别名: 1-(1,3-benzodioxol-5-yl)-1H-pyrrole；1-(1,3-benzodioxol-5-yl)pyrrole
• 化学式: C₁₁H₉NO₂
• mdl: MFCD02661659
• 分子量: 187.198
• InChiKey: KFNHLYASYVUCQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  一氧化碳 、 1-(benzo[d][1,3]dioxol-5-yl)-1H-pyrrole 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79%的产率得到6,7-methylenedioxy-9H-pyrrolo<1.2-a>indol-9-one
  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：

  在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 Aspergillus niger monoamine oxidase variant D₅ 作用下， 以 异辛烷 为溶剂， 反应 24.0h， 以57%的产率得到1-(benzo[d][1,3]dioxol-5-yl)-1H-pyrrole
  参考文献：
  名称：

  Unveiling the Biocatalytic Aromatizing Activity of Monoamine Oxidases MAO-N and 6-HDNO: Development of Chemoenzymatic Cascades for the Synthesis of Pyrroles

  摘要：

  A chemoenzymatic cascade process for the sustainable production of pyrroles has been developed. Pyrroles were synthesized by exploiting the previously unexplored aromatizing activity of monoamine oxidase enzymes (MAO-N and 6-HDNO). MAO-N/6-HDNO whole cell biocatalysts are able to convert 3-pyrrolines into pyrroles under mild conditions and in high yields. Moreover, MAO-N can work in combination with the ruthenium Grubbs catalyst, leading to the synthesis of pyrroles from diallylamines/-anilines in a one-pot cascade metathesis aromatization sequence.

  DOI：

  10.1021/acscatal.6b03081

文献信息

• Cascade Synthesis of Pyrroles from Nitroarenes with Benign Reductants Using a Heterogeneous Cobalt Catalyst
  作者：Pavel Ryabchuk、Thomas Leischner、Carsten Kreyenschulte、Anke Spannenberg、Kathrin Junge、Matthias Beller

  DOI：10.1002/anie.202007613

  日期：2020.10.12

  A bifunctional 3d‐metal catalyst for the cascade synthesis of diverse pyrroles from nitroarenes is presented. The optimal catalytic system Co/NGr‐C@SiO2‐L is obtained by pyrolysis of a cobalt‐impregnated composite followed by subsequent selective leaching. In the presence of this material, (transfer) hydrogenation of easily available nitroarenes and subsequent Paal–Knorr/Clauson‐Kass condensation provides

  提出了一种用于从硝基芳烃级联合成多种吡咯的双功能3d金属催化剂。最佳催化体系Co/NGr-C@SiO 2 -L是通过热解钴浸渍复合材料并随后进行选择性浸出而获得的。在这种材料的存在下，容易获得的硝基芳烃的（转移）氢化和随后的 Paal-Knorr/Clauson-Kass 缩合可使用二氢、甲酸或 CO/H 2 O混合物（WGSR条件）作为还原剂。除了有利的步骤经济性之外，这种简单的多米诺骨牌工艺不需要任何溶剂或外部助催化剂。该方法的一般合成效用在各种功能化底物上得到了证明，包括生物活性和药学相关化合物的制备，例如（+）-异沙莫坦。
• Sustainable Pathways to Pyrroles through Iron-Catalyzed<i>N</i>-Heterocyclization from Unsaturated Diols and Primary Amines
  作者：Tao Yan、Katalin Barta

  DOI：10.1002/cssc.201600607

  日期：2016.9.8

  pharmaceutically active compounds and play an important role in medicinal chemistry. Therefore, the development of new, atom‐economic, and sustainable catalytic strategies to obtain these moieties is highly desired. Direct catalytic pathways that utilize readily available alcohol substrates have been recently established; however, these approaches rely on the use of noble metals such as ruthenium or iridium

  吡咯是药物活性化合物中的重要骨架，并在药物化学中起重要作用。因此，迫切需要开发新的，原子经济的，可持续的催化策略来获得这些部分。最近已经建立了利用容易获得的醇底物的直接催化途径。然而，这些方法依赖于使用贵金属，例如钌或铱。在这里，我们报道了使用基于地球上大量廉价铁的催化剂直接合成吡咯的方法。该方法使用2-丁炔-1,4-二醇或2-丁烯-1,4-二醇，它们可以直接与苯胺，苄基胺和脂肪族胺偶合，以中到中度获得各种​​N-取代的吡咯优良的孤立产量。
• 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。
• Unveiling the Biocatalytic Aromatizing Activity of Monoamine Oxidases MAO-N and 6-HDNO: Development of Chemoenzymatic Cascades for the Synthesis of Pyrroles
  作者：Nicoló Scalacci、Gary W. Black、Giulio Mattedi、Nicola L. Brown、Nicholas J. Turner、Daniele Castagnolo

  DOI：10.1021/acscatal.6b03081

  日期：2017.2.3

  A chemoenzymatic cascade process for the sustainable production of pyrroles has been developed. Pyrroles were synthesized by exploiting the previously unexplored aromatizing activity of monoamine oxidase enzymes (MAO-N and 6-HDNO). MAO-N/6-HDNO whole cell biocatalysts are able to convert 3-pyrrolines into pyrroles under mild conditions and in high yields. Moreover, MAO-N can work in combination with the ruthenium Grubbs catalyst, leading to the synthesis of pyrroles from diallylamines/-anilines in a one-pot cascade metathesis aromatization sequence.