2-(m-tolyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine | 1159803-51-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(m-tolyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine
• 英文别名: 2-(3-Methylphenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine；3-(3-methylphenyl)-2,4-diaza-3-boratricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaene
• CAS: 1159803-51-6
• 化学式: C₁₇H₁₅BN₂
• 分子量: 258.13
• InChiKey: WWOCDJPTCDLFMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  对溴甲苯 、 2-(m-tolyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine 在 四(三苯基膦)钯 、 potassium tert-butylate 作用下， 以 1,4-二氧六环 为溶剂， 反应 21.0h， 以85%的产率得到3,4'-二甲基-1,1'-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：

  3-甲基苯硼酸 、 1,8-二氨基萘 以 水 为溶剂， 反应 2.0h， 以92%的产率得到2-(m-tolyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine
  参考文献：
  名称：

  无催化剂，环境友好的水上掩蔽卤代芳基硼酸R（烷基或芳基）-B（dan）的合成

  摘要：

  描述了一种在水上合成R（烷基或芳基）-B（dan）的环境友好方法。使1,8-二氨基萘（danH 2）与不同类型的有机硼酸反应，以中等至极好的收率提供产品。还进行了克级反应，以确保反应的可扩展性。

  DOI：

  10.1016/j.tet.2021.132205

文献信息

• 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）。
• 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。
• Direct Transformation from Arylamines to Aryl Naphthalene-1,8-diamino Boronamides: A Metal-Free Sandmeyer-Type Process
  作者：Siyi Ding、Qiang Ma、Min Zhu、Huaping Ren、Shaopeng Tian、Yuzhen Zhao、Zongcheng Miao

  DOI：10.3390/molecules24030377

  日期：——

  A direct metal-free transformation from arylamines to aryl naphthalene-1,8-diamino boronamides, a type of masked boronic acid, has been developed based on Sandmeyer-type reactions. A nonsymmetrical diboron reagent, B(pin)-B(dan), was utilized as the borylating reagent, and the B(dan) moiety was transferred to the aim products selectively. This conversion tolerated a series of functional groups, including

  已经基于 Sandmeyer 型反应开发了从芳胺到芳基萘-1,8-二氨基硼酰胺（一种掩蔽硼酸）的直接无金属转化。非对称二硼试剂 B(pin)-B(dan) 用作硼酸化试剂，B(dan) 部分选择性地转移到目标产品。这种转化耐受一系列官能团，包括氯、溴、氟、酯、羟基、氰基和酰胺。
• Direct Suzuki–Miyaura Coupling with Naphthalene-1,8-diaminato (dan)-Substituted Organoborons
  作者：Hiroto Yoshida、Michinari Seki、Shintaro Kamio、Hideya Tanaka、Yuki Izumi、Jialun Li、Itaru Osaka、Manabu Abe、Hiroki Andoh、Tomoki Yajima、Tomohiro Tani、Teruhisa Tsuchimoto

  DOI：10.1021/acscatal.9b03666

  日期：2020.1.3

  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.