2-(4-methoxyphenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine | 1159803-53-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(4-methoxyphenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine
• 英文别名: 2-(4-Methyoxyphenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine；3-(4-methoxyphenyl)-2,4-diaza-3-boratricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaene
• CAS: 1159803-53-8
• 化学式: C₁₇H₁₅BN₂O
• 分子量: 274.13
• InChiKey: WPAJPIWTDXMCKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  33.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine 、 4-碘氰基苯 在 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate 、 barium(II) hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以57%的产率得到4-甲氧基-4’-氰基联苯
  参考文献：
  名称：

  Direct Suzuki–Miyaura Coupling with Naphthalene-1,8-diaminato (dan)-Substituted Organoborons

  摘要：

  The actually direct Suzuki-Miyaura coupling with "protected" R-B(dan) (dan = naphthalene-1,8-diaminato) was demonstrated to smoothly occur without in situ deprotection of the B(dan) moiety. The use of t-BuOK (Ba(OH)(2) in some cases) as a base under anhydrous conditions is the key to the successful cross-coupling, where R B(dan) is readily converted into a transmetalation-active borate-form, regardless of the well-accepted diminished boron-Lewis acidity.

  DOI：

  10.1021/acscatal.9b03666
• 作为产物：
  描述：

  甲氧苯胺 在 咪唑 、 盐酸 、 iron(III) chloride 、 sodium nitrite 作用下， 以 水 、 乙腈 为溶剂， 反应 1.08h， 生成 2-(4-methoxyphenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine
  参考文献：
  名称：

  Sequential One-Pot Access to Molecular Diversity through Aniline Aqueous Borylation

  摘要：

  On the basis of our recently reported aniline aqueous borylation, molecular diversity was achieved in a one-pot process by combining other reactions such as esterification, Suzuki-Miyaura coupling, hydrogenolysis, or Petasis borono-Mannich.

  DOI：

  10.1021/jo501665e

文献信息

• Efficient metal-free photochemical borylation of aryl halides under batch and continuous-flow conditions
  作者：Kai Chen、Shuai Zhang、Pei He、Pengfei Li

  DOI：10.1039/c5sc04521e

  日期：——

  A rapid, chemoselective and metal-free C-B bond-forming reaction of aryl iodides and bromides in aqueous solution at low temperatures was discovered. This reaction is amenable to batch and continuous-flow conditions...

  发现了在低温下，水溶液中芳基碘化物和溴化物的快速，化学选择性和无金属的CB键形成反应。该反应适合间歇和连续流动条件...
• Direct introduction of a naphthalene-1,8-diamino boryl [B(dan)] group by a Pd-catalysed selective boryl transfer reaction
  作者：Liang Xu、Pengfei Li

  DOI：10.1039/c5cc00231a

  日期：——

  reagent, B(pin)-B(dan), has been utilised in the Pd-catalysed borylation of aryl bromides and chlorides. Remarkably selective formation of aryl-B(dan) bonds is established. This represents a direct and efficient way to introduce masked boronic acids. The synthetic usefulness of this reaction is demonstrated in the preparation of boron-differentiated di- and polyboron compounds.

  非对称二硼试剂B（pin）-B（dan）已用于芳基溴化物和氯化物在Pd催化的硼化反应中。建立了芳基-B（dan）键的显着选择性形成。这代表了引入掩蔽的硼酸的直接而有效的方法。该反应的合成有用性在硼分化的二硼和多硼化合物的制备中得到了证明。
• Transition metal-free B(dan)-installing reaction (dan: naphthalene-1,8-diaminato): H–B(dan) as a B(dan) electrophile
  作者：Jialun Li、Michinari Seki、Shintaro Kamio、Hiroto Yoshida

  DOI：10.1039/d0cc02560g

  日期：——

  H–B(dan) serves as a B(dan) electrophile to give directly R–B(dan) by the reaction with Grignard reagents under transition metal-free conditions.

  H-B（丹）作为B（丹）亲电试剂，通过与Grignard试剂在无过渡金属条件下反应，直接生成R-B（丹）。
• Diazaboryl‐naphthyl‐ketone: A New Scaffold with Bright Fluorescence, Aggregation‐Induced Emission, and Application in the Quantitation of Trace Boronic Acids in Drug Intermediates
  作者：Hannah E. Hackney、Marco Paladino、Hao Fu、Dennis G. Hall

  DOI：10.1002/chem.202003248

  日期：2020.11.11

  This study describes the synthesis, structure, and photophysical properties of a new luminescent polyaromatic boronic acid scaffold, diazaboryl‐naphthyl‐ketones (DNKs). These stable compounds display extremely bright fluorescence, aggregation‐induced emission, positive solvatochromism, and solid‐state fluorescence. DFT calculations and X‐ray crystallographic study revealed notable electronic and structural

  这项研究描述了一种新型的发光聚芳族硼酸支架，二氮杂硼烷基萘基酮（DNKs）的合成，结构和光物理性质。这些稳定的化合物显示出非常明亮的荧光，聚集诱导的发射，正溶剂溶变色和固态荧光。DFT计算和X射线晶体学研究表明，这些化合物与母体二氨基萘（DAN）加合物之间存在明显的电子和结构差异。DAN系统的酰化作用会导致HOMO和LUMO均定位在DNK单元上，这证实了B-芳基取代基的影响可忽略不计。LUMO能量降低，并且其形状显着改变。溶液和固态中的光物理数据显示蓝移，变窄，DNK排放量大（量子产率高达89％）。荧光DNK系统的潜在实用性已通过概念验证证明了，使用HPLC和荧光检测技术测定固体样品中痕量的硼酸污染物（低至1 ppm）。该方法可用于药物开发中的定量分析，该定量分析是从药物合成中较晚的交叉偶联反应中检测出的难以检测和潜在诱变的残留硼酸。
• Synthesis of masked haloareneboronic acids via iridium-catalyzed aromatic C–H borylation with 1,8-naphthalenediaminatoborane (danBH)
  作者：Noriyuki Iwadate、Michinori Suginome

  DOI：10.1016/j.jorganchem.2008.11.068

  日期：2009.5

  "Masked" areneboronic acids have been prepared by Ir-catalyzed C-H borylation of arenes. A [Ir(OMe)(cod)](2) complex with a DPPE ligand showed the highest catalytic activity in the C-H borylation of benzene at 80 degrees C. The reaction system can be applied to substituted arenes, including halogen-substituted arenes. 1,3-Dihalobenzenes undergo the C-H borylation at their 5-positions in a regioselective fashion, affording 3,5-dihaloareneboronic acid derivatives, which serve as useful coupling modules for the convergent dendrimer synthesis. (C) 2008 Elsevier B.V. All rights reserved.

  通过铱 (Ir)-催化的 C-H 键硼化反应，已成功制备了“屏蔽”的芳香族硼酸。含有 DPPE 配体的 [Ir(OMe)(cod)](2) 复合物在 80°C 下对苯的 C-H 键硼化反应表现出最高的催化活性。该反应体系可应用于取代芳香族物质，包括卤素取代的芳香族化合物。1,3-二卤苯在区域选择性条件下于其 5 位发生 C-H 键硼化反应，生成 3,5-二卤芳香族硼酸衍生物，这些衍生物可作为有用的偶联模块，用于收敛型树状大分子的合成。© 2008 Elsevier B.V. 保留所有权利。