叔-丁基二甲基(4-(4,4,5,5-四甲基-1,3,2-二硼戊环-2-基)苯氧基)硅烷 | 873426-76-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 叔-丁基二甲基(4-(4,4,5,5-四甲基-1,3,2-二硼戊环-2-基)苯氧基)硅烷
• 英文名称: tert-butyldimethyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)silane
• 英文别名: Tert-butyldimethyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)silane；tert-butyl-dimethyl-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]silane
• CAS: 873426-76-7
• 化学式: C₁₈H₃₁BO₃Si
• 分子量: 334.339
• InChiKey: HUHNCIBKFJVPQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  叔-丁基二甲基(4-(4,4,5,5-四甲基-1,3,2-二硼戊环-2-基)苯氧基)硅烷 在 四甲基乙二胺 、 magnesium bromide 、 iron(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 2.02h， 生成 tert-butyl(4-(difluoromethyl)phenoxy)dimethylsilane
  参考文献：
  名称：

  用砜试剂对芳基硼酸酯进行铁催化氟烷基化：超越还原电位的限制

  摘要：

  砜和芳基硼化合物之间的铁催化烷基-芳基偶联反应仍然是一个挑战。我们报告了第一个铁催化的芳基硼酸酯与 N-杂芳基砜的自由基二氟烷基化。铁催化剂与 N-杂芳基砜的氮原子之间的配位被认为对于克服分子间单电子转移过程中砜的还原电位限制很重要，这使得氟烷基 N-杂芳基砜（具有相对较高的还原电位）和非氟化烷基 N-杂芳基砜（具有低还原电位）作为强大的烷基化试剂。

  DOI：

  10.1002/anie.202102597
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 2.17h， 生成 叔-丁基二甲基(4-(4,4,5,5-四甲基-1,3,2-二硼戊环-2-基)苯氧基)硅烷
  参考文献：
  名称：

  Addition of Arylboronic Acids to Arylpropargyl Alcohols en Route to Indenes and Quinolines

  摘要：

  A regio- and stereoselective rhodium-catalyzed synthesis of trisubstituted allylic alcohols is described. The utility of these synthons is demonstrated in a convenient synthesis of indenes and quinolines.

  DOI：

  10.1021/ol202176g

文献信息

• Copper‐Photocatalyzed Borylation of Organic Halides under Batch and Continuous‐Flow Conditions
  作者：Antoine Nitelet、Damien Thevenet、Bruno Schiavi、Christophe Hardouin、Jean Fournier、Rodolphe Tamion、Xavier Pannecoucke、Philippe Jubault、Thomas Poisson

  DOI：10.1002/chem.201806345

  日期：——

  The copper‐photocatalyzed borylation of aryl, heteroaryl, vinyl and alkyl halides (I and Br) was reported. The reaction proceeded using a new heteroleptic Cu complex under irradiation with blue LEDs, giving the corresponding boronic‐acid esters in good to excellent yields. The reaction was extended to continuous‐flow conditions to allow an easy scale‐up. The mechanism of the reaction was studied and

  据报道，铜光催化的芳基，杂芳基，乙烯基和烷基卤化物（I和Br）的硼化反应。该反应在蓝色LED的照射下使用一种新型的杂铜配合物进行，从而得到了相应的硼酸酯，收率良好至极佳。反应扩展到连续流动条件，以易于放大。研究了该反应的机理，并提出了基于还原淬灭（Cu I / Cu I * / Cu 0）的机理。
• Synthesis and SAR studies of 3,6-disubstituted indazole derivatives as potent hepcidin production inhibitors
  作者：Takeshi Fukuda、Kenjiro Ueda、Takashi Ishiyama、Riki Goto、Sumie Muramatsu、Masami Hashimoto、Kengo Watanabe、Naoki Tanaka

  DOI：10.1016/j.bmcl.2017.03.056

  日期：2017.5

  hepcidin could be a strategy favorable to treating anemia of chronic disease (ACD). We report herein the synthesis and structure-activity relationships (SARs) of a series of indazole compounds as hepcidin production inhibitors. The optimization study of compound 1 led to a potent hepcidin production inhibitor 45, which showed serum hepcidin lowering effects in a mouse IL-6 induced acute inflammatory model

  铁调素已经成为系统性铁稳态的主要调节分子。抑制铁调素可能是一种有利于治疗慢性疾病性贫血（ACD）的策略。我们在此报告了一系列作为铁调素生产抑制剂的吲唑化合物的合成和构效关系（SAR）。化合物1的优化研究产生了有效的铁调素生成抑制剂45，该抑制剂在小鼠IL-6诱导的急性炎症模型中显示出血清铁调素降低的作用。
• Hydrogenation of Borylated Arenes
  作者：Marco Wollenburg、Daniel Moock、Frank Glorius

  DOI：10.1002/anie.201810714

  日期：2019.5.13

  abundant aryl boronic acids and their derivatives catalyzed by rhodium cyclic (alkyl)(amino)carbene (Rh–CAAC) is reported. The reaction tolerates a variety of boron‐protecting groups and provides direct access to a broad scope of saturated, borylated carbo‐ and heterocycles with various functional groups. The transformation is strategically important because the versatile saturated boronate products are

  据报道，环状（烷基）（氨基）卡宾铑（Rh–CAAC）催化了丰富的芳基硼酸及其衍生物的顺式选择性氢化。该反应可耐受各种硼保护基，并可以直接进入具有各种官能团的各种饱和，硼化的碳环和杂环。该转变在战略上很重要，因为通用的饱和硼酸酯产品很难用其他方法制备。硼基的后官能化证明了饱和环状结构单元的效用。
• SUBSTITUTED METHYL PYRAZOLOPYRIMIDINONE AND METHYL IMIDAZOPYRAZINONE COMPOUNDS AS PDE1 INHIBITORS
  申请人：Dart NeuroScience, LLC

  公开号：US20190177327A1

  公开（公告）日：2019-06-13

  A chemical entity of Formula (I) or Formula (II): wherein R a , R b , R e , and R f have any of the values described herein, and compositions comprising such chemical entities; methods of making them; and their use in a wide range of methods, including metabolic and reaction kinetic studies; detection and imaging techniques; radioactive treatments; modulating and treating disorders mediated by PDE1 activity or dopaminergic signaling; treating neurological disorders, CNS disorders, dementia, neurodegenerative diseases, and trauma-dependent losses of function; treating stroke, including cognitive and motor deficits during stroke rehabilitation; facilitating neuroprotection and neurorecovery; enhancing the efficiency of cognitive and motor training, including animal skill training protocols; and treating peripheral disorders, including cardiovascular, renal, hematological, gastroenterological, liver, cancer, fertility, and metabolic disorders.

  化学实体的化学式（I）或化学式（II）：其中Ra、Rb、Re和Rf可以具有本文中描述的任何值，以及包含这种化学实体的组合物；制备它们的方法；以及它们在各种方法中的使用，包括代谢和反应动力学研究；检测和成像技术；放射性治疗；调节和治疗由PDE1活性或多巴胺信号传导介导的疾病；治疗神经系统疾病、中枢神经系统疾病、痴呆、神经退行性疾病以及依赖创伤的功能丧失；治疗中风，包括中风康复期间的认知和运动功能障碍；促进神经保护和神经恢复；增强认知和运动训练的效率，包括动物技能训练方案；以及治疗外周疾病，包括心血管、肾脏、血液、胃肠、肝脏、癌症、生育和代谢紊乱。
• Base-Free Palladium-Catalyzed Borylation of Aryl Chlorides with Diborons
  作者：Yutaro Yamamoto、Hiroshi Matsubara、Hideki Yorimitsu、Atsuhiro Osuka

  DOI：10.1002/cctc.201600456

  日期：2016.7.20

  base‐free palladium‐catalyzed borylation of aryl chlorides with diborons was achieved. The base‐free conditions offered acceptable functional group compatibility. Based on experimental and computational studies, it was shown that smooth boryl transfer from the diborons to the arylpalladium chloride was promoted by strong interaction between the Lewis acidic boron and the chlorine atom on palladium.

  实现了无碱钯催化的芳基氯与二硼化的硼化反应。无碱条件提供了可接受的官能团兼容性。根据实验和计算研究，结果表明，路易斯酸性硼与钯上的氯原子之间的强相互作用促进了硼基从乙硼烷向氯化芳基钯的平稳转移。