三(甲氧基)硼烷 | 4832-27-3

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 中文名称: 三(甲氧基)硼烷
• 中文别名: 硼酸三甲酯-10B
• 英文名称: trimethyl borate-10
• 英文别名: trimethyl [10B]borate；trimethyl borate；Trimethylborat；Trimethylborat<¹⁰B>；[¹⁰B]boric acid trimethyl ester；[¹⁰B]Borsaeure-trimethylester；Trimethyl-[¹⁰B]borat；tris(methoxy)borane；Boric acid (H310BO3) trimethyl ester
• CAS: 4832-27-3
• 化学式: C₃H₉BO₃
• 分子量: 103.103
• InChiKey: WRECIMRULFAWHA-NUTRPMROSA-N

物化性质

• 熔点：
  −34 °C(lit.)
• 沸点：
  68-69 °C(lit.)
• 密度：
  0.915 g/mL at 25 °C(lit.)
• 闪点：
  -8 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -0.09
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  三(甲氧基)硼烷 、 8-iodo-harmine 在 碘 、 magnesium 、 水 作用下， 以 乙醚 为溶剂， 反应 5.0h， 生成 [10B]-8-dihydroxyboryl harmine
  参考文献：
  名称：

  Synthesis of 8-[10B]-dihydroxyboryl-harmine, a potential agent for boron neutron capture therapy

  摘要：

  DOI：

  10.1002/(sici)1099-1344(200001)43:1<97::aid-jlcr296>3.0.co;2-d
• 作为产物：
  描述：

  甲醇 在 硼酸-10B 作用下， 生成 三(甲氧基)硼烷
  参考文献：
  名称：

  Synthesis of 8-[10B]-dihydroxyboryl-harmine, a potential agent for boron neutron capture therapy

  摘要：

  DOI：

  10.1002/(sici)1099-1344(200001)43:1<97::aid-jlcr296>3.0.co;2-d
• 作为试剂：
  描述：

  2-(2-溴苯基)-1,3-二恶烷 在 正丁基锂 、 三(甲氧基)硼烷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 28.0h， 以55%的产率得到2-formylphenylboronic acid-¹⁰B
  参考文献：
  名称：

  Regiochemical Tagging:  A New Tool for Structural Characterization of Isomeric Components in Combinatorial Mixtures

  摘要：

  In this contribution we present a new combined synthetic and analytical strategy (regiochemical ragging) that allows facile determination of complete structure, including substituent position and regiochemistry, of mass-redundant components in complex combinatorial mixtures. The libraries of components (oxime ethers) are formed by the reaction of a mixture of substituents (aldehydes) with a scaffold containing several chemically similar attachment points (aminooxy groups), The structure of the resulting library components can then be determined from a combination of single MS and the tandem (MS/MS) spectra. Determination of the unique isomeric motif for each component is made possible via the following features of library design: (1) pan of the scafforld moiety, "transferable group" (the nitrogen atom from the oxime group) is transferred to the: substituent during fragmentation in the tandem experiment, (2) transferable groups on the scaffold differ from each other by either isotopic labels or fragmentation energies, and (3) mass-redundant substituents are isotopically labeled to create at least a 2 mass unit difference between them. The components of thr resulting library thus become labeled with different mass- and energy tags, which allows for precise regiochemical assignment of the functional group positions on the scaffold and substituents by mass spectrometry. The approach has been used to create and analyze a mixture of 27 isomeric compounds, each containing three boronic acid groups. The combination of the MS and MS/MS spectra of the tagged mixture has yielded a unique and structurally definitive signature of each component. Applications of the regiochemical tagging techniques to rapid synthesis and screening of combinatorial mixtures are discussed.

  DOI：

  10.1021/ja993844v

文献信息

• Preparation of Boric-10 Acid Applied in Shielded Materials of Nuclear Industry
  作者：Lei Zhang、Weijiang Zhang、Jiao Xu

  DOI：10.14233/ajchem.2015.16895

  日期：——

  Because of the superior features of boron-10 isotope in absorbing hot neutrons, boric-10 acid (H3 10BO3) has been used widely in nuclear industry, like as additive in primary loop of pressurized water reactor and as control rod and other shielded materials in nuclear reactor. Boric-10 acid is obtained from boron-10 trifluoride (10BF3) by esterification and hydrolyzation. In this study, the preparation of trimethyl borate-10 [(CH3O)3B] from boron-10 trifluoride (10BF3) obtained through chemical exchange rectification was investigated. The kinetics of esterification reaction was controlled by second order pseudo homogeneous reaction. The activation energy was 685.5 KJ/mol. In addition, the hydrolyzation of trimethyl borate-10 was investigated as a function of pH, temperature and molar ratio of water to trimethyl borate-10. Under optimum process conditions, higher yield of boric-10 acid with nuclear industrial purity grade was realized.

  由于硼-10 同位素在吸收热中子方面的优越特性，硼-10 酸（H3 10BO3）已被广泛应用于核工业，如压水堆一回路的添加剂和核反应堆中的控制棒及其他屏蔽材料。硼-10 酸是由三氟化硼（10BF3）通过酯化和水解反应得到的。本研究以化学交换整流法获得的三氟化硼（10BF3）为原料，研究了三甲基硼酸-10 [(CH3O)3B]的制备方法。酯化反应动力学受二阶伪均相反应控制。活化能为 685.5 KJ/mol。此外，还研究了三甲基硼酸-10 的水解与 pH 值、温度和水与三甲基硼酸-10 的摩尔比的函数关系。在最佳工艺条件下，获得了更高产率的核工业纯度级硼-10 酸。
• Design, Synthesis, and Biological Evaluation of Boron-Containing Macrocyclic Polyamines and Their Zinc(II) Complexes for Boron Neutron Capture Therapy
  作者：Hiroki Ueda、Minoru Suzuki、Reiko Kuroda、Tomohiro Tanaka、Shin Aoki

  DOI：10.1021/acs.jmedchem.1c00445

  日期：2021.6.24

  Boron neutron capture therapy (BNCT) is a binary therapeutic method for cancer treatment based on the use of a combination of a cancer-specific drug containing boron-10 (10B) and thermal neutron irradiation. For successful BNCT, 10B-containing molecules need to accumulate specifically in cancer cells, because destructive effect of the generated heavy particles is limited basically to boron-containing

  硼中子俘获疗法 (BNCT) 是一种基于结合使用含硼 10 ( 10 B)的癌症特异性药物和热中子辐射的癌症治疗的二元治疗方法。对于成功的 BNCT，需要在癌细胞中特异性地积累10个含 B 分子，因为产生的重粒子的破坏作用基本上仅限于含硼细胞。在此，我们报告了用 9、12 和 15 元大环多胺及其 Zn 2+功能化的硼化合物的设计和合成复合体。还报道了它们的细胞毒性、癌细胞和正常细胞的细胞内摄取活性以及 BNCT 效应。实验数据表明，单质子和/或双质子化形式的无金属 [12]aneN 4 - 和 [15]aneN 5 - 型配体被癌细胞吸收，它们与细胞内金属如 Zn 2+的复合物会诱导热中子辐照后的细胞死亡，可能是通过与 DNA 的相互作用。
• Design, Synthesis and Biological Evaluation of Boron‐Containing Macrocyclic Polyamine Dimers and Their Zinc(II) Complexes for Boron Neutron Capture Therapy
  作者：Hiroki Ueda、Minoru Suzuki、Yoshinori Sakurai、Tomohiro Tanaka、Shin Aoki

  DOI：10.1002/ejic.202100949

  日期：2022.2.16

  We report on the design, synthesis, and biological evaluation of DNA-targeting BNCT agents equipped with homo- and heterodimers of macrocyclic polyamines and their zinc(II) complexes. These 10B-compounds inhibit the growth of cancer cells due to generated heavy particles upon thermal neutron irradiation.

  我们报告了配备大环多胺及其锌 (II) 配合物的同二聚体和异二聚体的 DNA 靶向 BNCT 试剂的设计、合成和生物学评估。这10种 B 化合物由于在热中子照射下产生重粒子而抑制癌细胞的生长。
• A Facile High-Yield Synthesis of [10 B]-8-Dihydroxyboryl Harmine, a Potential Agent for Boron Neutron Capture Therapy
  作者：Jose Sintas、Norberto Macareno、Arturo Vitale

  DOI：10.3390/50300526

  日期：——

  n/a

  不适用
• Synthesis and evaluation as MRI probe of the trifluoromethylated p-boronophenylalanine and its alcohol derivative
  作者：Yoshihide Hattori、Hitoshi Yamamoto、Hideya Ando、Hirofumi Kondoh、Tomoyuki Asano、Mitsunori Kirihata、Yoshihiro Yamaguchi、Tateaki Wakamiya

  DOI：10.1016/j.bmc.2006.12.043

  日期：2007.3

  Boron-neutron capture therapy (BNCT) and magnetic resonance imaging (MRI) are quite attractive techniques for treatment and diagnosis of cancer, respectively. In order to develop practical tools for BNCT and MRI, novel compounds containing both the trifluoromethyl group and B-10 atom in a single molecule were designed. In the present study, p-boronophenylalanine and p-boronophenylalaninol with the trifluoromethyl group were synthesized, and F-19 NMR measurements of these compounds were carried out. (c) 2006 Elsevier Ltd. All rights reserved.