4,4-difluoro-1,3,5,7-tetramethyl-8-(2-furyl)-4-bora-3a,4a-diaza-s-indacene-3-ium-4-ide | 1416913-27-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4,4-difluoro-1,3,5,7-tetramethyl-8-(2-furyl)-4-bora-3a,4a-diaza-s-indacene-3-ium-4-ide
• 英文别名: 4,4-difluoro-1,3,5,7-tetramethyl-8-(2-furyl)-4-bora-3a,4a-diaza-s-indacene；5,5-Difluoro-10-(2-furyl)-1,3,7,9-tetramethyl-5H-dipyrrolo[1,2-c:2 inverted exclamation mark,1 inverted exclamation mark-f][1,3,2]diazaborinin-4-ium-5-uide；2,2-difluoro-8-(furan-2-yl)-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene
• CAS: 1416913-27-3
• 化学式: C₁₇H₁₇BF₂N₂O
• 分子量: 314.143
• InChiKey: TVGNGRIZFTXGBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  4,4-difluoro-1,3,5,7-tetramethyl-8-(2-furyl)-4-bora-3a,4a-diaza-s-indacene-3-ium-4-ide 、 对羟基苯甲醛 在 哌啶 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以50 %的产率得到
  参考文献：
  名称：

  CN115160350

  摘要：

  公开号：
• 作为产物：
  描述：

  在 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三氟化硼乙醚 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 16.0h， 以33 mg的产率得到4,4-difluoro-1,3,5,7-tetramethyl-8-(2-furyl)-4-bora-3a,4a-diaza-s-indacene-3-ium-4-ide
  参考文献：
  名称：

  Meso-thienyl and furyl rotor effects in BF₂-chelated dipyrrin dyes: solution spectroscopic studies and X-ray structural packing analysis of isomer and congener effects

  摘要：

  Well-defined discrete fluorescent molecular systems with very subtle steric/electronic differences are interesting when considering solid-state packing and solution substituent effects. Herein, we report the synthesis and characterization of four 4,4-difluoro-1,3,5,7-tetramethyl-8-(C4H3 X)-4-bora-3a,4a-diaza-s-indacene complexes (X?=?O, S). Various NMR spectroscopic experiments were used to assign all relevant atoms (CD2Cl2): 19F, 11B, 1H, 13C, 13CH undecoupled, 1H1H COSY, 1H1H NOESY, 1H13C HSQC, and 1H13C HMBC NMR spectroscopy. UV-Vis and fluorescence studies were undertaken for all compounds. Chemical shift differences were found between isomers and congeners; for congeners, aromatic d differences were attributed to electron-poor character. Also, compounds 14 were studied crystallographically. In the solid state, internal dihedral planes and intermolecular packing patterns can be compared.

  DOI：

  10.1080/00958972.2012.740023

文献信息

• The inorganic DMSO/POCl₃ reaction with BODIPY: wide product formation and implications for biological ROS sensing and neurodegenerative disease research
  作者：Taehong Jun、Kibong Kim、Kang Mun Lee、Dhiraj P. Murale、Atul P. Singh、Amgalan Natsagdorj、Hyunjeong Liew、Yoo-Hun Suh、David G. Churchill

  DOI：10.1142/s1088424612501180

  日期：2012.11

  We report a refined and expanded synthetic study of 4,4-difluoro-1,3,5,7-tetramethyl-8-(aryl)-4-bora-3a,4a-diaza-s-indacene under treatment with POCl₃/DMSO. The 2-chloro-6-methylsulfide derivative (Kim TI, Park S, Choi Y and Kim Y. Chem. Asian J. 2011; 6: 1358-61.) was one of five co-eluants, including 2,6-disulfido and -dichloro species, and mono-substituted counterparts. The 8-meso tail group modifies product distribution. The different sulfur-containing products undergo different "off-on" responses with NaOCl (10 equiv.). Compounds 4b and 2b exhibit low toxicity and were found to enter juxtanuclear regions in neuroblastoma.

  我们报告了用 POCl3/DMSO 处理 4,4-二氟-1,3,5,7-四甲基-8-(芳基)-4-bora-3a,4a-diaza-s-茚的精制和扩展合成研究。2-chloro-6-methylsulfide 衍生物（Kim TI、Park S、Choi Y 和 Kim Y. Chem. Asian J. 2011; 6: 1358-61.）是五种共助剂之一，其中包括 2,6-二磺酸基和二氯化物以及单取代的对应物。8-meso 尾基改变了产物的分布。不同的含硫产物在 NaOCl（10 等量）的作用下会产生不同的 "关闭-开启 "反应。化合物 4b 和 2b 显示出较低的毒性，并能进入神经母细胞瘤的并核区域。