1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-((triisopropylsilyl)oxy)benzene | 1021918-57-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-((triisopropylsilyl)oxy)benzene
• 英文别名: 4,4,5,5-Tetramethyl-2-[4-[[tris(1-methylethyl)silyl]oxy]phenyl]-1,3,2-dioxaborolane；tri(propan-2-yl)-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]silane
• CAS: 1021918-57-9
• 化学式: C₂₁H₃₇BO₃Si
• 分子量: 376.419
• InChiKey: IZPFFABULMFOFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  407.6±28.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-((triisopropylsilyl)oxy)benzene 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex 、 四丁基氟化铵 、 sodium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.17h， 生成 6-(4-hydroxyphenyl)-1-isobutyl-1H-imidazo[4,5-b]pyrazin-2(3H)-one
  参考文献：
  名称：

  Discovery and SAR exploration of a novel series of imidazo[4,5-b]pyrazin-2-ones as potent and selective mTOR kinase inhibitors

  摘要：

  We report here the discovery of a novel series of selective mTOR kinase inhibitors. A series of imidazo[ 4,5-b]pyrazin-2-ones, represented by screening hit 1, was developed into lead compounds with excellent mTOR potency and exquisite kinase selectivity. Potent compounds from this series show >1000-fold selectivity over the related PI3K alpha lipid kinase. Further, compounds such as 2 achieve mTOR pathway inhibition, blocking both mTORC1 and mTORC2 signaling, in PC3 cancer cells as measured by inhibition of pS6 and pAkt (S473). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.035
• 作为产物：
  描述：

  4-溴苯酚 在 咪唑 、 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex 、 potassium acetate 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-((triisopropylsilyl)oxy)benzene
  参考文献：
  名称：

  Discovery and SAR exploration of a novel series of imidazo[4,5-b]pyrazin-2-ones as potent and selective mTOR kinase inhibitors

  摘要：

  We report here the discovery of a novel series of selective mTOR kinase inhibitors. A series of imidazo[ 4,5-b]pyrazin-2-ones, represented by screening hit 1, was developed into lead compounds with excellent mTOR potency and exquisite kinase selectivity. Potent compounds from this series show >1000-fold selectivity over the related PI3K alpha lipid kinase. Further, compounds such as 2 achieve mTOR pathway inhibition, blocking both mTORC1 and mTORC2 signaling, in PC3 cancer cells as measured by inhibition of pS6 and pAkt (S473). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.035

文献信息

• Ligand‐Enabled Catalytic CH Arylation of Aliphatic Amines by a Four‐Membered‐Ring Cyclopalladation Pathway
  作者：Chuan He、Matthew J. Gaunt

  DOI：10.1002/anie.201508912

  日期：2015.12.21

  palladium‐catalyzed CH arylation of aliphatic amines with arylboronic esters is described, proceeding through a four‐membered‐ring cyclopalladation pathway. Crucial to the successful outcome of this reaction is the action of an amino‐acid‐derived ligand. A range of hindered secondary amines and arylboronic esters are compatible with this process and the products of the arylation can be advanced to

  描述了钯催化的脂肪族胺与芳基硼酸酯的CH芳基化，并通过四元环环钯途径进行。该反应成功的关键是氨基酸衍生的配体的作用。一系列受阻的仲胺和芳基硼酸酯与该方法相容，并且芳基化的产物可以通过连续的CH活化反应推进为复杂的多环分子。
• Rhodium-Catalyzed <i>ipso</i>-Borylation of Alkylthioarenes via C–S Bond Cleavage
  作者：Yuta Uetake、Takashi Niwa、Takamitsu Hosoya

  DOI：10.1021/acs.orglett.6b01250

  日期：2016.6.3

  Rhodium-catalyzed transformation of alkyl aryl sulfides into arylboronic acid pinacol esters via C–S bond cleavage is reported. In combination with transition-metal-catalyzed sulfanyl group-guided regioselective C–H borylation reactions of alkylthioarenes, this method allows the synthesis of a diverse range of multisubstituted arenes.

  据报道，铑通过CS键断裂将烷基芳基硫醚转变为芳基硼酸频哪醇酯。结合过渡金属催化的硫烷基通过烷基硫基芳烃进行的区域选择性C–H硼化反应，该方法可合成多种多样的多取代芳烃。
• Palladium-Catalyzed <i>ipso</i>-Borylation of Aryl Sulfides with Diborons
  作者：M. Bhanuchandra、Alexandre Baralle、Shinya Otsuka、Keisuke Nogi、Hideki Yorimitsu、Atsuhiro Osuka

  DOI：10.1021/acs.orglett.6b01305

  日期：2016.6.17

  ipso-borylation of aryl sulfides with diboron reagents has been achieved, providing arylboronate esters of synthetic use. The key conditions to transform inherently reluctant C–S bonds into C–B bonds include a palladium-NHC (N-heterocyclic carbene) precatalyst, bis(pinacolato)diboron, and lithium hexamethyldisilazide. This protocol is applicable to a reasonable range of aryl alkyl sulfides. Twofold borylation

  一种催化宫浦型本位与二硼试剂芳基硫化物的-borylation已经实现，从而提供合成的使用arylboronate酯。将本来就不愿意的C–S键转换为C–B键的关键条件包括钯-NHC（N-杂环卡宾）预催化剂，双（频哪醇）二硼和六甲基二硅叠氮化锂。该协议适用于合理范围的芳基烷基硫化物。在二苯硫醚的反应中观察到双重硼化。
• Remote steric control for undirected <i>meta</i> -selective C–H activation of arenes
  作者：Boobalan Ramadoss、Yushu Jin、Sobi Asako、Laurean Ilies

  DOI：10.1126/science.abm7599

  日期：2022.2.11

  Regioselective functionalization of arenes remains a challenging problem in organic synthesis. Steric interactions are often used to block sites adjacent to a given substituent, but they do not distinguish the remaining remote sites. We report a strategy based on remote steric control, whereby a roof-like ligand protects the distant para site in addition to the ortho sites, and thereby enables selective

  芳烃的区域选择性功能化仍然是有机合成中的一个具有挑战性的问题。空间相互作用通常用于封闭与给定取代基相邻的位点，但它们不区分剩余的远程位点。我们报告了一种基于远程空间控制的策略，其中屋顶状配体保护遥远的对网站除了邻位点，从而使选择性激活元没有碳氢（C-H）键邻要么对取代基。我们展示了铱催化的这一概念元-各种单取代芳烃的选择性硼基化，包括复杂的药物分子。这种策略有可能将 C-H 键功能化的工具箱扩展到以前不可区分的反应位点。
• 중합성 화합물 및 이의 액정 디스플레이에서의 용도
  申请人：MERCK PATENT GMBH 메르크 파텐트 게엠베하(519980656531)

  公开号：KR20190126853A

  公开（公告）日：2019-11-12

  본 발명은 중합성 화합물, 이의 제조 방법 및 중간체, 이를 포함하는 액정(LC) 매질, 및 중합성 화합물 및 액정 매질의 광학, 전자-광학 및 전자적 목적, 특히 액정 디스플레이, 특히 중합체 지속성 정렬 유형의 액정 디스플레이에서의 용도에 관한 것이다.

  这项发明涉及到聚合物化合物、其制备方法和中间体、包含它的液晶（LC）介质、以及聚合物化合物和液晶介质的光学、电子光学和电子目的，特别是液晶显示器的应用，特别是在聚合物持续定向类型的液晶显示器中的应用。