4,4-difluoro-8-(3-benzothienyl)-4-bora-3α,4α-diaza-s-indacene | 1086633-37-5

• 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: 4,4-difluoro-8-(3-benzothienyl)-4-bora-3α,4α-diaza-s-indacene
• 英文别名: 10-(3-Benzothienyl)-5,5-difluoro-5H-dipyrrolo[1,2-c:2 inverted exclamation mark,1 inverted exclamation mark-f][1,3,2]diazaborinin-4-ium-5-uide；8-(1-benzothiophen-3-yl)-2,2-difluoro-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene
• CAS: 1086633-37-5
• 化学式: C₁₇H₁₁BF₂N₂S
• 分子量: 324.162
• InChiKey: UJBJJTFVZNEGJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-噻吩基锂 、 4,4-difluoro-8-(3-benzothienyl)-4-bora-3α,4α-diaza-s-indacene 以 not given 为溶剂， 生成 10-(benzo[b]thiophen-3-yl)-5,5,7-tri(thiophen-2-yl)-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium
  参考文献：
  名称：

  Optical Effects of S-Oxidation and Mⁿ⁺ Binding in meso-Thienyl Dipyrrin Systems and of Stepwise Bromination of 4,4-Difluoro-8-(2,5-dibromo-3-thienyl)-4-bora-3a,4a-diaza-s-indacene

  摘要：

  We report 16 novel species and 8 molecular structures in studying how meso-thienyl-substituted dipyrrole oxidation, bromination, and metal ion binding impart optical changes, as monitored by UV-vis absorption/emission spectroscopy. Treatment of 4,4-difluoro-8-(3-benzothienyl)-4-bora-3a,4a-diaza-s-indacene (phi(F) = 0.19) with m-CPBA gives selective S-dioxidation (phi(F) = 0.006). Results of titrations of transition metal- and "scorpionate"-like dipyrrin species varied under room temperature treatment of m-CPBA. Ni-(thienyl-dipyrrin), (n = 2) degraded significantly in the presence of m-CPBA, whereas related species (M = Cu, Fe, Co; n = 2, 3) were inert. meso-Thienyl group properties were revealed through the use of 3,4,4-triphenyl-8-(thienyl)-4-bora-3a,4a-diaza-s-indacene; Cu2+ addition resulted in smooth absorption decreases which were modeled to support 1:1 substrate: M2+ binding; for Hg2+ 1:2 substrate: M2+ binding was found. Treatment of 4,4-difluoro-8-(2,5-dibromo-3-thienyl)-4-bora-3a, 4a-diaza-s-indacene with Br-2 gave red-shifted UV-vis absorption band features that grow with increasing dipyrrin bromination. Structures of the di- and tetra-substituted bromination products were obtained.

  DOI：

  10.1021/ic801354y
• 作为产物：
  描述：

  、 三氟化硼乙醚 在 DDQ 作用下， 以 not given 为溶剂， 生成 4,4-difluoro-8-(3-benzothienyl)-4-bora-3α,4α-diaza-s-indacene
  参考文献：
  名称：

  Optical Effects of S-Oxidation and Mⁿ⁺ Binding in meso-Thienyl Dipyrrin Systems and of Stepwise Bromination of 4,4-Difluoro-8-(2,5-dibromo-3-thienyl)-4-bora-3a,4a-diaza-s-indacene

  摘要：

  We report 16 novel species and 8 molecular structures in studying how meso-thienyl-substituted dipyrrole oxidation, bromination, and metal ion binding impart optical changes, as monitored by UV-vis absorption/emission spectroscopy. Treatment of 4,4-difluoro-8-(3-benzothienyl)-4-bora-3a,4a-diaza-s-indacene (phi(F) = 0.19) with m-CPBA gives selective S-dioxidation (phi(F) = 0.006). Results of titrations of transition metal- and "scorpionate"-like dipyrrin species varied under room temperature treatment of m-CPBA. Ni-(thienyl-dipyrrin), (n = 2) degraded significantly in the presence of m-CPBA, whereas related species (M = Cu, Fe, Co; n = 2, 3) were inert. meso-Thienyl group properties were revealed through the use of 3,4,4-triphenyl-8-(thienyl)-4-bora-3a,4a-diaza-s-indacene; Cu2+ addition resulted in smooth absorption decreases which were modeled to support 1:1 substrate: M2+ binding; for Hg2+ 1:2 substrate: M2+ binding was found. Treatment of 4,4-difluoro-8-(2,5-dibromo-3-thienyl)-4-bora-3a, 4a-diaza-s-indacene with Br-2 gave red-shifted UV-vis absorption band features that grow with increasing dipyrrin bromination. Structures of the di- and tetra-substituted bromination products were obtained.

  DOI：

  10.1021/ic801354y

文献信息

• Optical Effects of <i>S</i>-Oxidation and M^<i>n</i>+ Binding in <i>meso</i>-Thienyl Dipyrrin Systems and of Stepwise Bromination of 4,4-Difluoro-8-(2,5-dibromo-3-thienyl)-4-bora-3<i>a</i>,4<i>a</i>-diaza-<i>s</i>-indacene
  作者：Shin Hei Choi、Kibong Kim、June Jeon、Bhupal Meka、Daniela Bucella、Keliang Pang、Snehadrinarayan Khatua、Junseong Lee、David G. Churchill

  DOI：10.1021/ic801354y

  日期：2008.12.1

  We report 16 novel species and 8 molecular structures in studying how meso-thienyl-substituted dipyrrole oxidation, bromination, and metal ion binding impart optical changes, as monitored by UV-vis absorption/emission spectroscopy. Treatment of 4,4-difluoro-8-(3-benzothienyl)-4-bora-3a,4a-diaza-s-indacene (phi(F) = 0.19) with m-CPBA gives selective S-dioxidation (phi(F) = 0.006). Results of titrations of transition metal- and "scorpionate"-like dipyrrin species varied under room temperature treatment of m-CPBA. Ni-(thienyl-dipyrrin), (n = 2) degraded significantly in the presence of m-CPBA, whereas related species (M = Cu, Fe, Co; n = 2, 3) were inert. meso-Thienyl group properties were revealed through the use of 3,4,4-triphenyl-8-(thienyl)-4-bora-3a,4a-diaza-s-indacene; Cu2+ addition resulted in smooth absorption decreases which were modeled to support 1:1 substrate: M2+ binding; for Hg2+ 1:2 substrate: M2+ binding was found. Treatment of 4,4-difluoro-8-(2,5-dibromo-3-thienyl)-4-bora-3a, 4a-diaza-s-indacene with Br-2 gave red-shifted UV-vis absorption band features that grow with increasing dipyrrin bromination. Structures of the di- and tetra-substituted bromination products were obtained.