thianaphtheno[3,2-b]pyrrole-2-carboxylic acid | 18646-98-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: thianaphtheno[3,2-b]pyrrole-2-carboxylic acid
• 英文别名: Thionaphtheno<3,2-b>pyrrol-carbonsaeure-(2)；Thionaphtheno[3,2-b]pyrrol-carbonsaeure-(2)；1H-[1]benzothiolo[3,2-b]pyrrole-2-carboxylic acid
• CAS: 18646-98-5
• 化学式: C₁₁H₇NO₂S
• 分子量: 217.248
• InChiKey: WIIZTTRLZUGHAN-UHFFFAOYSA-N

物化性质

• 熔点：
  229-230 °C
• 沸点：
  519.2±30.0 °C(Predicted)
• 密度：
  1.574±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  thianaphtheno[3,2-b]pyrrole-2-carboxylic acid 在 喹啉 、 铜 作用下， 以0.56 g的产率得到1H-[1]benzothieno[3,2-b]pyrrole
  参考文献：
  名称：

  HOF·CH 3 CN合成氧化噻吩并吡咯

  摘要：

  通过使用HOF·CH 3 CN络合物，可以在一定范围的噻吩并吡咯中将硫原子有效转化为磺酰基。温和的条件，高收率和易于纯化是该新途径的主要特征。相对于母体化合物，大多数新材料在UV /可见光范围内均显示出可观的红移吸收。

  DOI：

  10.1021/jo200534p
• 作为产物：
  描述：

  1-苯并噻酚-2-羧醛 在 sodium hydroxide 、 sodium ethanolate 作用下， 以 乙醇 、 水 为溶剂， 反应 2.5h， 生成 thianaphtheno[3,2-b]pyrrole-2-carboxylic acid
  参考文献：
  名称：

  4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) Dyes Modified for Extended Conjugation and Restricted Bond Rotations

  摘要：

  Five new, constrained, aryl-substituted 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes (3f,g and 4h-j) were prepared and investigated to see if they have more favorable fluorescence characteristics than the unconstrained systems 2 that were prepared in previous studies. Dye types 3 and 4 have relatively rigid conformations caused by the heteroatom (3f and 3g) or ethylene bridge (4h-j) linkers that preclude free rotation of the substituted-benzene molecular fragments. In the event, the new dye types 3 and 4 have longer lambda(max) (abs) (620-660 nm) and lambda(max) (fluor) (630-680 nm) values than compounds 2, They also exhibit higher extinction coefficients (>100 000 M (1) cm(-1) except for 3g). Their fluorescent quantum yields are high (up to 0.72 for 4j), with the exception of compound 3g, which has a quantum yield of only 0.05. The redox properties of dyes 3 and 4 have also been examined.

  DOI：

  10.1021/jo991927o

文献信息

• Synthesis and CHK1 inhibitory potency of Hymenialdisine analogues
  作者：Jean-Gilles Parmentier、Bernard Portevin、Roy M. Golsteyn、Alain Pierré、John Hickman、Philippe Gloanec、Guillaume De Nanteuil

  DOI：10.1016/j.bmcl.2008.12.001

  日期：2009.2

  A series of thieno[3,2-b]pyrroloazepinones derivatives related to Hymenialdisine were prepared and tested for CHK1 inhibitory activity. Nanomolar inhibitions were achieved when electron-withdrawing substituents were introduced at position 3 of the thiophene ring. (C) 2008 Elsevier Ltd. All rights reserved.
• 4,4-Difluoro-4-bora-3a,4a-diaza-<i>s</i>-indacene (BODIPY) Dyes Modified for Extended Conjugation and Restricted Bond Rotations
  作者：Jiong Chen、Armin Burghart、Agnes Derecskei-Kovacs、Kevin Burgess

  DOI：10.1021/jo991927o

  日期：2000.5.1

  Five new, constrained, aryl-substituted 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes (3f,g and 4h-j) were prepared and investigated to see if they have more favorable fluorescence characteristics than the unconstrained systems 2 that were prepared in previous studies. Dye types 3 and 4 have relatively rigid conformations caused by the heteroatom (3f and 3g) or ethylene bridge (4h-j) linkers that preclude free rotation of the substituted-benzene molecular fragments. In the event, the new dye types 3 and 4 have longer lambda(max) (abs) (620-660 nm) and lambda(max) (fluor) (630-680 nm) values than compounds 2, They also exhibit higher extinction coefficients (>100 000 M (1) cm(-1) except for 3g). Their fluorescent quantum yields are high (up to 0.72 for 4j), with the exception of compound 3g, which has a quantum yield of only 0.05. The redox properties of dyes 3 and 4 have also been examined.
• Synthesis of Oxidized Thienopyrroles using HOF·CH₃CN
  作者：Neta Shefer、Shlomo Rozen

  DOI：10.1021/jo200534p

  日期：2011.6.3

  An efficient transformation of the sulfur atoms to the sulfonyl group in a range of thienopyrroles was achieved by using the HOF·CH3CN complex. Mild conditions, high yields, and easy purification are the main features of this novel route. Most new materials exhibit considerable red-shift absorptions in the UV/visible range relative to the parent compounds.

  通过使用HOF·CH 3 CN络合物，可以在一定范围的噻吩并吡咯中将硫原子有效转化为磺酰基。温和的条件，高收率和易于纯化是该新途径的主要特征。相对于母体化合物，大多数新材料在UV /可见光范围内均显示出可观的红移吸收。