2-(2'-bromophenyl)-6-butyl-1,3,6,2-dioxazaborocan | 1008106-85-1

• 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: 2-(2'-bromophenyl)-6-butyl-1,3,6,2-dioxazaborocan
• 英文别名: (4R,8S)-8-(2-Bromophenyl)-4-butylhexahydro-[1,3,2]oxazaborolo[2,3-B][1,3,2]oxazaborol-4-ium-8-uide；1-(2-bromophenyl)-5-butyl-2,8-dioxa-5-azonia-1-boranuidabicyclo[3.3.0]octane
• CAS: 1008106-85-1
• 化学式: C₁₄H₂₁BBrNO₂
• 分子量: 326.041
• InChiKey: XIXCATUAWFQSTK-UHFFFAOYSA-N

物化性质

• 熔点：
  91-93 °C

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  2-(2'-bromophenyl)-6-butyl-1,3,6,2-dioxazaborocan 在 正丁基锂 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 生成 3,3-二甲基-6-硝基苯并[C][1,2]氧杂硼杂环-1(3H)-醇
  参考文献：
  名称：

  [EN] BORON-CONTAINING SMALL MOLECULES AS ANTIPROTOZOAL AGENTS
  [FR] PETITES MOLÉCULES CONTENANT DU BORE ET UTILISABLES EN TANT QU'AGENTS ANTIPROTOZOAIRES

  摘要：

  这项发明提供了用于治疗原虫感染的新化合物，包含这些化合物的药物组合物，以及这些化合物与至少一种额外治疗有效剂的组合物。这些化合物具有以下结构式：其中X选自取代苯基、取代或未取代杂环芳基和未取代环烷基的组；R3a选自H1未取代的C1或C2或C3或C4或C5或C6烷基和未取代的C3或C4或C5或C6环烷基的组；R3b选自H、未取代的C1或C2或C3或C4或C5或C6烷基和未取代的C3或C4或C5或C6环烷基的组；但R3a和R3b，以及它们连接的原子，可选地结合形成3、4、5或6元环，但R3a和R3b不能同时为H，或其盐。

  公开号：

  WO2011019618A1
• 作为产物：
  描述：

  N-丁基二乙醇胺 、 2-溴苯基硼酸 以 甲苯 为溶剂， 反应 2.0h， 以98.6%的产率得到2-(2'-bromophenyl)-6-butyl-1,3,6,2-dioxazaborocan
  参考文献：
  名称：

  环结构和芳香取代基对苯并恶唑药效团 pKa 的影响

  摘要：

  在这项工作中，我们对一类独特的芳香硼酸苯并氧杂硼的物理性质进行了研究。使用分光光度法，确定了一系列取代苯并氧杂硼的电离常数。检查杂环修饰以确定它们对硼酸部分电离的影响。还表明，芳环的取代基效应与化合物的测量 p K a遵循哈米特关系值。最后，这些取代作用也显示出在生理相关条件下扩展到这些化合物的糖结合特性。结合起来，这些数据将为希望定制此类化合物的电离和/或结合含二醇生物分子的能力的药物化学家提供信息。

  DOI：

  10.1021/ml200215j

文献信息

• Benzosiloxaboroles: Silicon Benzoxaborole Congeners with Improved Lewis Acidity, High Diol Affinity, and Potent Bioactivity
  作者：Aleksandra Brzozowska、Paweł Ćwik、Krzysztof Durka、Tomasz Kliś、Agnieszka E. Laudy、Sergiusz Luliński、Janusz Serwatowski、Stefan Tyski、Mateusz Urban、Wojciech Wróblewski

  DOI：10.1021/acs.organomet.5b00265

  日期：2015.6.22

  2-(dimethylsilyl)phenylboronates apparently occurs through intramolecular dehydrogenative cyclization reaction in the presence of water. Unlike the case for benzosiloxaborole, the formation of its analogue containing a thiophene ring is thermodynamically unfavorable, which was confirmed by theoretical calculations. The presence of a B–O–Si linkage results in increased Lewis acidity with respect to the

  介绍了重要一类杂环化合物的硅类似物苯并氧杂硼烷的合成和理化性质。它们是通过（2-溴苯基）硼酸酯与n的卤素-锂交换反应制备的-BuLi，然后将（2-lithiophenyl）二甲基硅烷进行甲硅烷基化或硼化。显然，在水的存在下，通过分子内脱氢环化反应实现了所生成的2-（二甲基甲硅烷基）苯基硼酸酯的环化。与苯并硅氧烷基硼烷的情况不同，其包含噻吩环的类似物的形成在热力学上是不利的，这通过理论计算得到了证实。与类似的苯并氧杂硼烷相比，B-O-Si键的存在会导致Lewis酸度增加。通过氟化或在硅原子上引入苯基，可以大大提高酸度。所选化合物显示出良好的抗真菌活性，因此它们是潜在的小分子治疗剂。
• Spiroboronate Si-rhodamine as a near-infrared probe for imaging lysosomes based on the reversible ring-opening process
  作者：Weiwei Zhu、Xiaoyun Chai、Baogang Wang、Yan Zou、Ting Wang、Qingguo Meng、Qiuye Wu

  DOI：10.1039/c5cc02496j

  日期：——

  A cyclic boronate structure was incorporated into Si-rhodamine to design a pH-activatable near-infrared (NIR) probe based on the reversible ring-opening process.

  一个环状硼酸酯结构被引入到Si-罗丹明中，以设计一种基于可逆环开启过程的pH活化近红外（NIR）探针。
• High-Yield Syntheses and Reactivity Studies of 1,2-Diborylated and 1,2,4,5-Tetraborylated Benzenes
  作者：Ömer Seven、Michael Bolte、Hans-Wolfram Lerner、Matthias Wagner

  DOI：10.1021/om500104w

  日期：2014.3.10

  Treatment of 1,2-dibromobenzene (1,2-C6H4Br2) or 1,2,4,5-tetrabromobenzene (1,2,4,5-C6H2Br4) with 2 equiv or 4 equiv of n-BuLi in the presence of excess iso-propoxy(pinacol)borane ((i-PrO)Bpin) furnishes 1,2-C6H4(Br)(Bpin) (1) or 1,4,2,5-C6F12(Br)(2)(Bpin)(2) (3) with excellent selectivity. The subsequent reaction of 1 or 3 with Mg turnings and more (i-PrO)Bpin gives the di- and tetraborylated benzenes 1,2-C6H4(Bpin)(2) (2) and 1,2,4,5-C6F12(Bpin)(4) (4) in overall yields of about 65%. For the Grignard transformation step, it is essential to continuously add 1 equiv (1) or 2 equiv (3) of 1,2-dibromoethane as an entrainer over a period of 1 h. Compounds 1 and 2 have been transformed into the ortho-functionalized trihydroborates Li[1,2-C6H4(Br)(BH3)] (Li[7]) and Li[1,2-C6H4(Bpin)(BH3)] (Li[8]) by means of 1 equiv of Li[AlH4]. Using 3 equiv of Li[AlH4], 2 can also be converted into the ditopic lithium trihydroborate Li-2[1,2-C6H4(BH3)(2)] (Li-2[9]); even the tetratopic derivative Li-4[1,2,4,5-C6F12(BH3)(4)] (Li-4[10]) is accessible from 4 and 4 equiv of Li[AlH4]. The compounds Li[7], Li[8], Li-2[9], and Li-4[10] have been crystallographically characterized as ether solvates, but still show Ar-BH3-eta(2)-Li interactions as the dominant mode of coordination. In the cases of Li-2[9] and Li-4[10] an intricate three-dimensional network and a zigzag polymer, respectively, are established by the contact ion pairs in the crystal lattice.
• The ratiometric fluorescence nanoparticle based on SiRB for pH detection of tumor
  作者：Qinghui Wang、Xiaoyu Ding、Yuhui Wang、Qian Du、Tianguo Xu、Bin Du、Hanchun Yao

  DOI：10.1016/j.ejps.2018.03.015

  日期：2018.6

  Tumor pH detection and pH value change monitoring have been of great interest in the field of nanomedicine. In this study, a pH-sensitive near-infrared fluorescence probe SiRB (Si-rhodamine and Boronic acid group) was synthesized by introducing a boronic acid group into the silicon rhodamine structure. ICG (Indocyanine green) as the fluorescence internal standard and SiRB were loaded into PLGA (poly lactic-co-glycolic acid) to form PLGA-SiRB-ICG nanoparticle. The experiments showed that the size of the nanoparticle was about 90 nm, which can reach tumor passively by enhancing permeability and retention effect. PLGA in the acidic environment will accelerate the release of cleavage, and the fluorescence ratio of the two probes can reflect the specific pH value in the tumor. The results indicated that the nanoparticle could quantitatively measure the pH value of the tumor site, which is expected to be used in tumor research and treatment.