10H-二苯并[B,E][1,4]氧杂硼杂环己烷-10-醇 | 19014-28-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 10H-二苯并[B,E][1,4]氧杂硼杂环己烷-10-醇
• 英文名称: 10H-dibenzo[b,e][1,4]oxaborinin-10-ol
• 英文别名: 10-Hydroxy-9-oxa-10-bora-anthracen；10-hydroxybenzo[b][1,4]benzoxaborinine
• CAS: 19014-28-9
• 化学式: C₁₂H₉BO₂
• 分子量: 196.013
• InChiKey: VXYFPDIBAOEMHM-UHFFFAOYSA-N

物化性质

• 熔点：
  285 °C(Solv: benzene (71-43-2); cyclohexane (110-82-7))
• 沸点：
  343.3±35.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.89
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存放在冷冻环境中，应置于低于-20°C的惰性气氛中。

反应信息

• 作为反应物：
  描述：

  10H-二苯并[B,E][1,4]氧杂硼杂环己烷-10-醇 在 碘 、 palladium diacetate 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以90%的产率得到二苯并呋喃
  参考文献：
  名称：

  由二芳基醚有效合成二苯并黄嘌呤醇及其在二苯并呋喃合成中的应用

  摘要：

  AbstractA convenient and efficient method for the borylation of diaryl ethers leading to dibenzoxaborininols and the synthesis of dibenzofuran derivatives has been developed. The borylation involves the sequential three‐step process: lithiation, borylation and hydrolysis. The synthesized dibenzoxaborininols could be readily transformed into dibenzofuran derivatives in good to excellent yields under palladium catalysis in the presence of iodine, and this is the first example for the formation of an aryl CC bond from diarylborinic acids.magnified image

  DOI：

  10.1002/adsc.201300567
• 作为产物：
  描述：

  二苯醚 在 正丁基锂 、 硫酸 、 水 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 生成 10H-二苯并[B,E][1,4]氧杂硼杂环己烷-10-醇
  参考文献：
  名称：

  Efficient 8-oxyquinolinato emitters based on a 9,10-dihydro-9,10-diboraanthracene scaffold for applications in optoelectronic devices

  摘要：

  二苯并蒽双(氧基喹啉酮)配合物被用于构建高效的绿色OLED。

  DOI：

  10.1039/c4tc02350a
• 作为试剂：
  描述：

  cyclohexyloxyallene 在 copper(ll) sulfate pentahydrate 、 palladium diacetate 、 sodium ascorbate 、 N,N-二异丙基乙胺 、 (1R,2R)-(+)-1,2-二氨基环己烷-N,N′-双(2-苯基膦-1-萘酰基) 、 10H-二苯并[B,E][1,4]氧杂硼杂环己烷-10-醇 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 51.0h， 生成
  参考文献：
  名称：

  Asymmetric Pd/Organoboron‐Catalyzed Site‐Selective Carbohydrate Functionalization with Alkoxyallenes Involving Noncovalent Stereocontrol

  摘要：

  Herein, we demonstrate the robustness of a synergistic chiral Pd/organoboron system in tackling a challenging suite of site‐, regio‐, enantio‐ and diastereoselectivity issues across a considerable palette of biologically relevant carbohydrate polyols, when prochiral alkoxyallenes were employed as electrophiles. In view of the burgeoning role of noncovalent interactions (NCIs) in stereoselective carbohydrate synthesis, our mechanistic experiments and DFT modeling of the reaction path unexpectedly revealed that NCIs such as hydrogen bonding and CH‐π interactions between the resting states of the Pd‐π‐allyl complex and the borinate saccharide are critically involved in the stereoselectivity control. Our strategy thus illuminates the untapped potential of harnessing NCIs in the context of transition metal catalysis to tackle stereoselectivity challenges in carbohydrate functionalization.

  DOI：

  10.1002/anie.202400912

文献信息

• Catalytic Double Carbon-Boron Bond Formation for the Synthesis of Cyclic Diarylborinic Acids as Versatile Building Blocks for π-Extended Heteroarenes
  作者：Takuya Igarashi、Mamoru Tobisu、Naoto Chatani

  DOI：10.1002/anie.201612535

  日期：2017.2.13

  catalytic synthesis of cyclic diarylborinic acids is developed using a dihydroaminoborane reagent as the boron source. Unlike previously reported methods that use organolithium reagents, this method allows the easy synthesis of cyclic diarylborinic acids bearing a range of functionalities including CN, CO2Et, CONEt2 and NMeCO2tBu. Furthermore, these cyclic diarylborinic acids provide rapid access to

  环状二芳基硼酸的第一次催化合成是使用二氢氨基硼烷试剂作为硼源进行的。与先前报道的使用有机锂试剂的方法不同，该方法可轻松合成带有CN，CO 2 Et，CONEt 2和NMeCO 2 t Bu等一系列功能的环状二芳基硼酸。此外，这些环状二芳基硼酸提供了快速进入骨骼多样性的途径，尤其是它们能够通过简单的交叉偶联反应合成六元至九元π扩展的杂芳烃，这在先进材料和药物中都是重要的合成靶标。
• INTRACELLULAR CALCIUM CONCENTRATION INCREASE INHIBITORS
  申请人：Mikoshiba, Katsuhiko

  公开号：EP1444981A1

  公开（公告）日：2004-08-11

  An intracellular calcium concentration increase inhibitor containing as the active ingredient (1) a boron compound represented by the formula (I). The compound represented by the formula (I) inhibits the increase of the intracellular calcium concentration, and therefore it is deemed to be useful as an agent for the prophylaxis and/or treatment of platelet aggregation, ischemic diseases in hearts and brains, immune deficiency diseases, allorgosis, bronchial asthma, hypertension, cerebrovascular spasm, various renal diseases, pancreatitis, Alzheimer's disease, etc.

  一种含有活性成分的细胞内钙浓度增加抑制剂，其活性成分为（1）由化学式（I）表示的硼化合物。化学式（I）表示的化合物抑制细胞内钙浓度的增加，因此被认为可用作预防和/或治疗血小板聚集、心脑缺血疾病、免疫缺陷疾病、变态反应、支气管哮喘、高血压、脑血管痉挛、各种肾脏疾病、胰腺炎、阿尔茨海默病等的药物。
• Synthesis of Borinic Acids and Borinate Adducts Using Diisopropylaminoborane
  作者：Ludovic Marciasini、Bastien Cacciuttolo、Michel Vaultier、Mathieu Pucheault

  DOI：10.1021/acs.orglett.5b01620

  日期：2015.7.17

  situ formation of aryl Grignard under Barbier condition and diisopropylaminoborane as boron source allows a complete control of the addition onto the boron electrophile. Analytically pure borinic acid derivatives were produced at the gram scale without column chromatography and isolated as borinates adducts, with ethanolamine or 8-hydroxyquinoline, after workup.

  在Barbier条件下原位形成芳基格氏试剂，并用二异丙基氨基硼烷作为硼源，可以完全控制向亲电硼的添加。在没有柱色谱的情况下，以克级产生分析纯的硼酸衍生物，并在后处理后与乙醇胺或8-羟基喹啉分离为硼酸酯加合物。
• Synthesis of benzannulated heterocycles by twofold Suzuki–Miyaura couplings of cyclic diarylborinic acids
  作者：Elena Dimitrijević、Madeline Cusimano、Mark S. Taylor

  DOI：10.1039/c3ob42065e

  日期：——

  Two-fold Suzuki–Miyaura cross-couplings of cyclic diarylborinic acids are described. This novel annulation method enables the synthesis of benzo-fused heterocycles from dihaloarenes or gem-dibromoolefins.

  描述了循环二芳基硼酸的双重铃木–宫浦交叉偶联。这种新颖的闭环方法使得从二氯芳烃或共二溴烯烃合成苯并融合杂环成为可能。
• Light blue and green thermally activated delayed fluorescence from 10H-phenoxaborin-derivatives and their application to organic light-emitting diodes
  作者：Yuichi Kitamoto、Taketo Namikawa、Dai Ikemizu、Yasuo Miyata、Takatsugu Suzuki、Hiroshi Kita、Tetsuo Sato、Shuichi Oi

  DOI：10.1039/c5tc01380a

  日期：——

  New luminescent compounds consisting of 10H-phenoxaboryl groups show excellent PLQYs and EQEs.

  新的发光化合物由10个H-苯氧硼基团组成，展现出优秀的光致发光量子产率（PLQYs）和外量子效率（EQEs）。