1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-phenothiazine | 1219637-89-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-phenothiazine
• 英文别名: (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-phenothiazine
• CAS: 1219637-89-4
• 化学式: C₁₈H₂₀BNO₂S
• 分子量: 325.239
• InChiKey: QIFDCQVAEPNKCR-UHFFFAOYSA-N

物化性质

• 沸点：
  484.9±34.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-phenothiazine 、 4-Tert-butyl-2-[3-(4-tert-butylpyridin-2-yl)phenyl]-6-chloropyridine 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 以64 %的产率得到1-[4-tert-butyl-6-[3-(4-tert-butylpyridin-2-yl)phenyl]pyridin-2-yl]-10H-phenothiazine
  参考文献：
  名称：

  WO2023/71719

  摘要：

  公开号：
• 作为产物：
  描述：

  吩噻嗪 、 联硼酸频那醇酯 、 频那醇硼烷 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ diethylsilane or dimethylchlorosilane/N(CH₂CH₃)3 、 catalyst: (Ir(C₈H₁₂)Cl)2/(NC₅H₄C(CH₃)3-4)2 作用下， 以 tetrahydrofuran 为溶剂， 以67%的产率得到1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-phenothiazine
  参考文献：
  名称：

  Iridium-Catalyzed, Silyl-Directed Borylation of Nitrogen-Containing Heterocycles

  摘要：

  Selective methods for the functionalization of indoles and other nitrogen heterocycles would provide access to the core structures of many natural products and pharmaceuticals. Although there are many methods and strategies for the synthesis of substituted indoles or functionalization of the azole ring, strategies for the selective functionalization of the benzo-fused portion of the indole skeleton, particularly the 7-position, are less common. We report a one-pot, iridium-catalyzed, silyl-directed C-H borylation of indoles at the 7-position. This process occurs in high yield with a variety of substituted indoles, and conversions of the 7-borylindole products to 7-aryl-, 7-cinnamyl-, and 7-haloindoles are demonstrated. The Ir-catalyzed, silyl-directed C-H borylation also occurs with several other nitrogen heterocycles, including carbazole, phenothiazines, and tetrahydroquinoline. The utility of this methodology is highlighted by the one-pot synthesis of a member of the pyrrolophenanthridone class of alkaloid natural products.

  DOI：

  10.1021/ja1006405

文献信息

• Doping Polycyclic Arenes with Nitrogen–Boron–Nitrogen (NBN) Units
  作者：Deng-Tao Yang、Tomoya Nakamura、Zhechang He、Xiang Wang、Atsushi Wakamiya、Tai Peng、Suning Wang

  DOI：10.1021/acs.orglett.8b02850

  日期：2018.11.2

  With the aid of borylation and oxidative coupling reactions, six new polycyclic aromatic hydrocarbons (PAHs) doped by nitrogen–boron–nitrogen (NBN) units were achieved. The structure–optoelectronic property relationship for this group of compounds was examined. All six compounds are fluorescent with contrasting emission colors and quantum yields.

  借助于硼化和氧化偶联反应，获得了六种由氮-硼-氮（NBN）单元掺杂的新的多环芳烃（PAH）。研究了这组化合物的结构与光电性质的关系。所有六个化合物都是荧光的，具有相反的发射颜色和量子产率。