6-Methoxy-2-(6-methoxy-pyridin-2-yl)-2H-benzo[d][1,2,3]diazaborinin-1-ol | 279676-31-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-Methoxy-2-(6-methoxy-pyridin-2-yl)-2H-benzo[d][1,2,3]diazaborinin-1-ol
• 英文别名: 1-Hydroxy-6-methoxy-2-(6-methoxypyridin-2-yl)-2,3,1-benzodiazaborinine
• CAS: 279676-31-2
• 化学式: C₁₄H₁₄BN₃O₃
• 分子量: 283.094
• InChiKey: HNFNBVCIZRVAMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.64
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-Methoxy-2-(6-methoxy-pyridin-2-yl)-2H-benzo[d][1,2,3]diazaborinin-1-ol 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 1,2-dihydro-1,6-dihydroxy-2-(2-methoxy-6-pyridyl)-2,3,1-benzodiazaborine
  参考文献：
  名称：

  A boron-containing estrogen mimic

  摘要：

  A prototype of a new class of 2,3,1-benzodiazaborine-based estrogen mimics is described. 1,2-Dihydro-1, 6-dihydroxy-2-(2-methoxy-6-pyridyl)-2,3,1-benzodiazaborine, (6), was obtained as a crystalline monohydrate (C13H12BN3O3. H2O) after regioselective BBr3-mediated O-demethylation of the condensation product formed from 2-formyl-4-methoxybenzeneboronic acid and 2-hydrazino-6-methoxypyridine. As intended by design, the solid-state structure of (6) features an intramolecular hydrogen-bond association between the donor B-OH group and the acceptor pyridine ring N, a connection which constitutes an additional 'virtual' six-membered ring, thereby providing for an overall topography closely matching that of a tetracyclic steroid. Specifically, prototype (6) can be viewed as a boron-containing mimic of the O17-methyl ether derivatives of dihydroequilenin or estradiol.

  DOI：

  10.1107/s0108270199007520
• 作为产物：
  描述：

  2-氯-6-甲氧基吡啶 在 肼 作用下， 以 乙醇 为溶剂， 生成 6-Methoxy-2-(6-methoxy-pyridin-2-yl)-2H-benzo[d][1,2,3]diazaborinin-1-ol
  参考文献：
  名称：

  A boron-containing estrogen mimic

  摘要：

  A prototype of a new class of 2,3,1-benzodiazaborine-based estrogen mimics is described. 1,2-Dihydro-1, 6-dihydroxy-2-(2-methoxy-6-pyridyl)-2,3,1-benzodiazaborine, (6), was obtained as a crystalline monohydrate (C13H12BN3O3. H2O) after regioselective BBr3-mediated O-demethylation of the condensation product formed from 2-formyl-4-methoxybenzeneboronic acid and 2-hydrazino-6-methoxypyridine. As intended by design, the solid-state structure of (6) features an intramolecular hydrogen-bond association between the donor B-OH group and the acceptor pyridine ring N, a connection which constitutes an additional 'virtual' six-membered ring, thereby providing for an overall topography closely matching that of a tetracyclic steroid. Specifically, prototype (6) can be viewed as a boron-containing mimic of the O17-methyl ether derivatives of dihydroequilenin or estradiol.

  DOI：

  10.1107/s0108270199007520

文献信息

• A boron-containing estrogen mimic
  作者：P. D. Robinson、M. P. Groziak

  DOI：10.1107/s0108270199007520

  日期：1999.10.15

  A prototype of a new class of 2,3,1-benzodiazaborine-based estrogen mimics is described. 1,2-Dihydro-1, 6-dihydroxy-2-(2-methoxy-6-pyridyl)-2,3,1-benzodiazaborine, (6), was obtained as a crystalline monohydrate (C13H12BN3O3. H2O) after regioselective BBr3-mediated O-demethylation of the condensation product formed from 2-formyl-4-methoxybenzeneboronic acid and 2-hydrazino-6-methoxypyridine. As intended by design, the solid-state structure of (6) features an intramolecular hydrogen-bond association between the donor B-OH group and the acceptor pyridine ring N, a connection which constitutes an additional 'virtual' six-membered ring, thereby providing for an overall topography closely matching that of a tetracyclic steroid. Specifically, prototype (6) can be viewed as a boron-containing mimic of the O17-methyl ether derivatives of dihydroequilenin or estradiol.