3,6-bis(5'-bromo-4'-hexyl-2,2'-bithiophen-5-yl)-2,5-dioctylpyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione | 1220883-03-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 3,6-bis(5'-bromo-4'-hexyl-2,2'-bithiophen-5-yl)-2,5-dioctylpyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
• CAS: 1220883-03-3
• 化学式: C₅₀H₆₆Br₂N₂O₂S₄
• 分子量: 1015.16
• InChiKey: NZDUOQAOFDKPEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.56
• 重原子数：
  60.0
• 可旋转键数：
  28.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  40.62
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  3,6-bis(4'-hexyl-2,2'-bithiophen-5-yl)-2,5-dioctylpyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以56%的产率得到3,6-bis(5'-bromo-4'-hexyl-2,2'-bithiophen-5-yl)-2,5-dioctylpyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
  参考文献：
  名称：

  Synthesis of diketopyrrolopyrrole (DPP) derivatives comprising bithiophene moieties

  摘要：

  Herein we disclose an easily applicable method for the synthesis of diketopyrrolopyrrole (DPP) derivatives comprising bithiophene moieties, with different substituents on the nitrogen atoms (Me, n-octyl, 3,5-di-tert-butylbenzyl, Boc) and on the thiophene rings (C6H13, C12H25), in good yields and purities. A comparison is made between the previously described method from literature and our more efficient approach regarding number of steps, overall yields and ease of synthesis and purification. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.01.027

文献信息

• Pd-catalyzed oxidative cross-coupling between two electron rich heteroarenes
  作者：Chun-Yang He、Zhen Wang、Cai-Zhi Wu、Feng-Ling Qing、Xingang Zhang

  DOI：10.1039/c3sc51278a

  日期：——

  The transition-metal-catalyzed oxidative cross-coupling between two coupling partners with similar structure and electronic characteristics remains a challenge owing to difficulty in suppressing undesired homo-couplings. We herein report a Pd-catalyzed oxidative cross-coupling between two thiophenes under mild reaction conditions. This approach can also be extended to furans. Some notable advantages

  具有相似结构和电子特性的两个偶联配偶之间的过渡金属催化的氧化交叉偶联由于难以抑制不希望的均相偶联而仍然是一个挑战。我们在本文中报道了在温和的反应条件下，两个噻吩之间的Pd催化的氧化交叉偶联。这种方法也可以扩展到呋喃。该反应的一些显着优点在于其合成简单，省去了有毒的锡烷偶联伙伴，并且具有出色的官能团相容性。该协议的特征使其成为构建电子和光电子材料中感兴趣的2,2'-噻吩-噻吩键合的理想策略。