dimethyl 3,4-bis(4-chlorophenyl)-1H-pyrrole-2,5-dicarboxlate | 1144503-30-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: dimethyl 3,4-bis(4-chlorophenyl)-1H-pyrrole-2,5-dicarboxlate
• 英文别名: dimethyl 3,4-bis(4-chlorophenyl)-1H-pyrrole-2,5-dicarboxylate；dimethyl 3,4-bis(4-chlorophenyl)pyrrole-2,5-dicarboxylate
• CAS: 1144503-30-9
• 化学式: C₂₀H₁₅Cl₂NO₄
• 分子量: 404.249
• InChiKey: OBYYBHIAWVKKMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl 3,4-bis(4-chlorophenyl)-1H-pyrrole-2,5-dicarboxlate 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 0.75h， 以83%的产率得到methyl 3,4-bis(4-chlorophenyl)-5-(hydroxymethyl)-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Selective Mono-reduction of Pyrrole-2,5 and 2,4-Dicarboxylates

  摘要：

  吡咯-2,5-二羧酸酯在0°C下使用3倍等摩尔的二异丁基铝氢化物迅速且选择性地还原为相应的单醇。吡咯-2,4-二羧酸酯显示出相同的反应性；然而，吡咯-3,4-二羧酸酯的选择性有所降低。当吡咯-2,5-二羧酸酯的氮原子被苄基保护时，选择性单还原不再发生。考虑到在相同条件下呋喃-2,5-二羧酸酯并未产生相应的单醇，显然，未保护的吡咯氮原子在此选择性单还原反应中起着重要作用。

  DOI：

  10.1248/cpb.c16-00122
• 作为产物：
  描述：

  PCPA甲酯 在 copper diacetate 、 sodium acetate 、 manganese triacetate 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 以79%的产率得到dimethyl 3,4-bis(4-chlorophenyl)-1H-pyrrole-2,5-dicarboxlate
  参考文献：
  名称：

  铜/锰共氧化环化从氨基酸酯合成高度取代的吡咯衍生物：莱考加鲁宾C和铬吡咯酸仿生合成的策略

  摘要：

  通过促进Cu（OAc）2与Mn（OAc）3的结合，已经开发了一种有效，简洁的方法，可以从容易获得的氨基酸酯中合成四取代的吡咯。该反应通过多次脱氢，脱氨基和氧化环化而进行。这种氧化的系统可以承受带有各种给电子或吸电子基团的底物。用这种方法，已经有效地制备了几种天然产物的关键中间体，并且高效地完成了糖木蛋白C和色吡咯酸的全部合成。

  DOI：

  10.1021/jo500740w

文献信息

• Development of novel pyrrole synthesis for the preparation of intermediates of bioactive pyrrole alkaloids
  作者：Eiko Yasui、Masao Wada、Norio Takamura

  DOI：10.1016/j.tetlet.2009.06.012

  日期：2009.8

  We have developed a novel method for the synthesis of 3,4-diarylpyrrole-2,5-dicarboxylates via α-diazo esters, which are easily obtained from phenylalanine derivatives. Utilizing this method, intermediates of bioactive compounds having the structure of 3,4-diarylpyrrole-2,5-dicarboxylates were synthesized.

  我们已经开发了一种通过α-重氮酯合成3,4-二芳基吡咯-2,5-二羧酸酯的新颖方法，该酯很容易从苯丙氨酸衍生物中获得。使用该方法，合成了具有3，4-二芳基吡咯-2，5-二羧酸酯结构的生物活性化合物的中间体。
• A General Method for the Synthesis of N-Unsubstituted 3,4-Diarylpyrrole-2,5-dicarboxylates
  作者：Masatomo Iwao、Tsutomu Fukuda、Yukie Hayashida

  DOI：10.3987/com-08-s(f)89

  日期：——

  A general method for the synthesis of N-unsubstituted 3,4-diarylpyrrole-2,5-dicarboxylates (3) has been developed. The key reactions involved are the Hinsberg-type synthesis of dimethyl N-benzyl-3,4-dihydroxypyrrole-2,5-dicarboxylate (6) followed by palladium-catalyzed Suzuki-Miyaura coupling of its bis-triflate derivative (7). The N-benzyl protecting group of the resulting 3,4-diarylpyrrole-2,5-dicarboxylates (8) is cleanly removed under hydrogenolytic or solvolytic conditions.
• A novel method for the synthesis of 3,4-disubstitutedpyrrole-2,5-dicarboxylates from hydrazones derived from α-diazo esters
  作者：Eiko Yasui、Masao Wada、Shinji Nagumo、Norio Takamura

  DOI：10.1016/j.tet.2013.03.037

  日期：2013.5

  Hydrazones obtained from alpha-diazo esters were converted to pyrroles when heated with thionyl chloride in alcohol. Among hydrazones, those substituted with a benzene ring on the beta-carbon to the ester are likely to give pyrroles in good yields. (C) 2013 Elsevier Ltd. All rights reserved.
• Cu/Mn Co-oxidized Cyclization for the Synthesis of Highly Substituted Pyrrole Derivatives from Amino Acid Esters: A Strategy for the Biomimetic Syntheses of Lycogarubin C and Chromopyrrolic Acid
  作者：Nini Zhou、Tao Xie、Lin Liu、Zhixiang Xie

  DOI：10.1021/jo500740w

  日期：2014.7.3

  An effective and concise approach to synthesis of tetrasubstituted pyrroles from readily available amino acid esters by the promotion of Cu(OAc)2 in conjunction with Mn(OAc)3 has been developed. This reaction proceeds through multiple dehydrogenations, deamination, and oxidative cyclization. This oxidized system tolerates substrates bearing various electron-donating or electron-withdrawing groups.

  通过促进Cu（OAc）2与Mn（OAc）3的结合，已经开发了一种有效，简洁的方法，可以从容易获得的氨基酸酯中合成四取代的吡咯。该反应通过多次脱氢，脱氨基和氧化环化而进行。这种氧化的系统可以承受带有各种给电子或吸电子基团的底物。用这种方法，已经有效地制备了几种天然产物的关键中间体，并且高效地完成了糖木蛋白C和色吡咯酸的全部合成。
• Selective Mono-reduction of Pyrrole-2,5 and 2,4-Dicarboxylates
  作者：Eiko Yasui、Jyunpei Tsuda、Satoshi Ohnuki、Shinji Nagumo

  DOI：10.1248/cpb.c16-00122

  日期：——

  Pyrrole-2,5-dicarboxylates were rapidly and selectively reduced to the corresponding mono-alcohol using 3 eq of diisobutylaluminum hydride at 0°C. Pyrrole-2,4-dicarboxylate showed the same reactivity; however, the selectivity decreased with pyrrole-3,4-dicarboxylate. When the nitrogen atom of the pyrrole-2,5-dicarboxylate is protected with a benzyl group, selective mono-reduction does not occur. Considering that furan-2,5-dicarboxylates did not give the corresponding mono-alcohol under the same conditions, the unprotected nitrogen atom of pyrrole apparently plays an important role in this selective mono-reduction.

  吡咯-2,5-二羧酸酯在0°C下使用3倍等摩尔的二异丁基铝氢化物迅速且选择性地还原为相应的单醇。吡咯-2,4-二羧酸酯显示出相同的反应性；然而，吡咯-3,4-二羧酸酯的选择性有所降低。当吡咯-2,5-二羧酸酯的氮原子被苄基保护时，选择性单还原不再发生。考虑到在相同条件下呋喃-2,5-二羧酸酯并未产生相应的单醇，显然，未保护的吡咯氮原子在此选择性单还原反应中起着重要作用。