methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthoate | 409369-93-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthoate
• 英文别名: Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthoate；methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-2-carboxylate
• CAS: 409369-93-3
• 化学式: C₁₈H₂₁BO₄
• 分子量: 312.173
• InChiKey: PAUIXQJXAOSPHP-UHFFFAOYSA-N

物化性质

• 沸点：
  451.1±28.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthoate 在 四(三苯基膦)钯 sodium hydroxide 、 叠氮磷酸二苯酯 、 sodium carbonate 、 三乙胺 、 三氟乙酸 、 N,N-二乙基苯胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 邻二氯苯 、 甲苯 为溶剂， 反应 67.5h， 生成 1-methyl-4-chlorobenzo(g)imidazo(4,5-c)quinoline
  参考文献：
  名称：

  Synthesis and biological evaluation of 4-amino derivatives of benzimidazoquinoxaline, benzimidazoquinoline, and benzopyrazoloquinazoline as potent IKK inhibitors

  摘要：

  We have recently identified BMS-345541 (1) as a highly selective and potent inhibitor of IKK-2 (IC50 = 0.30 mu M), which however was considerably less potent against IKK-1 (IC50 = 4.0 mu M). In order to further explore the SAR around the imidazoquinoxaline tricyclic structure of 1, we prepared a series of tetracyclic analogues (7, 13, and 18). The synthesis and biological activities of these potent IKK inhibitors are described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.017
• 作为产物：
  描述：

  3-碘萘-2-羧酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 硫酸 、 potassium acetate 作用下， 以 二甲基亚砜 为溶剂， 反应 31.0h， 生成 methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthoate
  参考文献：
  名称：

  Synthesis and biological evaluation of 4-amino derivatives of benzimidazoquinoxaline, benzimidazoquinoline, and benzopyrazoloquinazoline as potent IKK inhibitors

  摘要：

  We have recently identified BMS-345541 (1) as a highly selective and potent inhibitor of IKK-2 (IC50 = 0.30 mu M), which however was considerably less potent against IKK-1 (IC50 = 4.0 mu M). In order to further explore the SAR around the imidazoquinoxaline tricyclic structure of 1, we prepared a series of tetracyclic analogues (7, 13, and 18). The synthesis and biological activities of these potent IKK inhibitors are described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.017

文献信息

• Rhodium(II)-Catalyzed Cyclization of Bis(N-tosylhydrazone)s: An Efficient Approach towards Polycyclic Aromatic Compounds
  作者：Ying Xia、Zhenxing Liu、Qing Xiao、Peiyuan Qu、Rui Ge、Yan Zhang、Jianbo Wang

  DOI：10.1002/anie.201201374

  日期：2012.6.4

  Ahead of the PAC: Polycyclic aromatic compounds (PACs) can be easily accessed by the combination of Suzuki–Miyaura cross‐coupling and a [Rh2(OAc)4]‐catalyzed carbene reaction using easily available bis(N‐tosylhydrazone)s as intermediates (see scheme; Ts=4‐toluenesulfonyl).

  在PAC之前：通过将Suzuki–Miyaura交叉偶联和[Rh 2（OAc）4 ]催化的卡宾反应结合使用，可轻松获得多环芳族化合物（PAC），方法是使用双（N-甲苯磺酰hydr）作为中间体（参见方案； Ts = 4-甲苯磺酰基）。
• Methods of treating inflammatory and immune diseases using inhibitors of IκB kinase (IKK)
  申请人：Burke James R.

  公开号：US06869956B2

  公开（公告）日：2005-03-22

  The present invention describes methods of preventing and treating inflammatory and immune-related diseases or disorders using inhibitors of IκB kinase (IKK). Also described are IKK inhibitors effective for the prevention and treatment of inflammatory and immune-related diseases or disorders, as demonstrated in vivo. Further embodiments of the present invention relate to a specific IKK inhibitors, 4(2′-aminoethyl)amino-1,8-dimethylimidazo(1,2-a) quinoxaline and compounds of formula (I), salts thereof, and pharmaceutical compositions.

  本发明描述了利用IκB激酶（IKK）抑制剂预防和治疗炎症和免疫相关疾病或紊乱的方法。还描述了在体内证明有效用于预防和治疗炎症和免疫相关疾病或紊乱的IKK抑制剂。本发明的进一步实施方式涉及特定的IKK抑制剂，如4(2′-氨乙基)氨基-1,8-二甲基咪唑并[1,2-a]喹喔啉和化合物的结构式(I)，其盐和药物组合物。
• Synthesis and Molecular Properties of Partially Fluorinated DNTTs**
  作者：Matthias W. Tripp、Daniel Bischof、Maximilian Dreher、Gregor Witte、Ulrich Koert

  DOI：10.1002/ejoc.202001635

  日期：2021.2.25

  Partially fluorinated dinaphthothienothiophenes (DNTTs) were synthesized via bisthiomethyl alkene intermediates which were accessible by McMurry coupling or Wittig olefination of partially fluorinated naphthalene precursors. The electronic structure of the DNTTs is compared with thiophene and fluorinated naphthalene units.

  通过双硫代甲基烯烃中间体合成部分氟化的二萘噻吩并噻吩（DNTT），该中间体可通过部分氟化的萘前体的McMurry偶联或Wittig烯化来获得。将DNTT的电子结构与噻吩和氟化萘单元进行了比较。
• Excellent Semiconductors Based on Tetracenotetracene and Pentacenopentacene: From Stable Closed-Shell to Singlet Open-Shell
  作者：Tanguy Jousselin-Oba、Masashi Mamada、Jérôme Marrot、Antoine Maignan、Chihaya Adachi、Abderrahim Yassar、Michel Frigoli

  DOI：10.1021/jacs.9b03488

  日期：2019.6.12

  Their biradical characteristics were found to be 0.50 and 0.64. The origin of the open-shell character of PP is related to the concomitant opening of two tetracenes with the recovering of two extra aromatic sextets and a small HOMO-LUMO energy gap (gap <1.5 eV). Thanks to the high stability, thin film OFET devices could be fabricated. In TG-BC configuration PP shows a remarkably high hole mobility of

  通过修改分子有机半导体的 π 拓扑结构来设计稳定的开壳有机材料最近引起了相当大的关注。然而，它们在有机场效应晶体管 (OFET) 中作为有源层的用途非常有限，所获得的空穴和电子电荷迁移率约为 10-3 cm2 V-1 s-1。在此，我们公开了两种周围融合材料的合成，即所谓的四苯并五苯 (TT) 和并五苯并五苯 (PP)，它们的带隙分别为 1.79 和 1.42 eV。它们的基态性质已经通过不同的实验进行了研究，包括稳态吸收、电子自旋共振、超导量子干涉装置和变温 NMR 以及 DFT 计算。TT和PP在基态下分别具有闭壳结构和单线态开壳结构，具有较高的稳定性。发现它们的双基特征为 0.50 和 0.64。PP 开壳特性的起源与两个并四苯的同时打开以及两个额外芳香六重体的恢复和小的 HOMO-LUMO 能隙（间隙 <1.5 eV）有关。由于高稳定性，可以制造薄膜 OFET 器件。在 TG-BC
• Methods of treating inflammatory and immune diseases using inhibitors of IkappaB kinase (IKK)
  申请人：——

  公开号：US20030022898A1

  公开（公告）日：2003-01-30

  The present invention describes methods of preventing and treating inflammatory and immune-related diseases or disorders using inhibitors of I&kgr;B kinase (IKK). Also described are IKK inhibitors effective for the prevention and treatment of inflammatory and immune-related diseases or disorders, as demonstrated in vivo. Further embodiments of the present invention relate to a specific IKK inhibitors, 4(2′-aminoethyl)amino-1,8-dimethylimidazo(1,2-a) quinoxaline and compounds of formula (I), salts thereof, and pharmaceutical compositions.

  本发明描述了使用I&kgr;B激酶（IKK）抑制剂预防和治疗炎症和免疫相关疾病或疾病的方法。还描述了在体内证明有效预防和治疗炎症和免疫相关疾病或疾病的IKK抑制剂。本发明的进一步实施方式涉及特定的IKK抑制剂，即4（2'-氨基乙基）氨基-1,8-二甲基咪唑并（1,2-a）喹啉及其式（I）的化合物，其盐和制药组合物。