tris[3,4-bis(benzyloxy)phenyl]boroxin | 911694-16-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: tris[3,4-bis(benzyloxy)phenyl]boroxin
• 英文别名: 2,4,6-Tris[3,4-bis(phenylmethoxy)phenyl]-1,3,5,2,4,6-trioxatriborinane；2,4,6-tris[3,4-bis(phenylmethoxy)phenyl]-1,3,5,2,4,6-trioxatriborinane
• CAS: 911694-16-1
• 化学式: C₆₀H₅₁B₃O₉
• 分子量: 948.493
• InChiKey: MQOHVJSVPQEGRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.71
• 重原子数：
  72
• 可旋转键数：
  21
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-{(1S)-1-[(benzyloxy)methyl]-2-methylpropyl}-N-[(1E)-[(2R)-5-iodo-2-methyl-3,4-dihydropyridin-1(2H)-yl](phenyl)methylidene]amine 、 tris[3,4-bis(benzyloxy)phenyl]boroxin 在 二(三叔丁基膦)钯 、 potassium tert-butylate 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 12.0h， 以97%的产率得到N-[(1S)-1-((benzyloxy)methyl)-2-methylpropyl]-N-[(1E)-[(2R)-5-[3,4-bis(benzyloxy)phenyl]-2-methyl-3,4-dihydropyridin-1(2H)-yl](phenyl)methylidene]amine
  参考文献：
  名称：

  New Methodology Toward Chiral, Non-Racemic 2,5-cis-Substituted Piperidines via Suzuki Cross-Coupling

  摘要：

  1,2,3,4-Tetrahydropyridines were halogenated upon treatment with iodine to obtain the desired cross-coupling precursors. Diastereoselective hydrogenation of Suzuki cross-coupling adducts allowed the facile asymmetric synthesis of 2,5-cis-substituted piperidines in five steps from readily available pyridine.

  DOI：

  10.1021/ol061415d
• 作为产物：
  描述：

  1,2-双(苄氧基)-4-溴苯 在 正丁基锂 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 1.17h， 生成 tris[3,4-bis(benzyloxy)phenyl]boroxin
  参考文献：
  名称：

  New Methodology Toward Chiral, Non-Racemic 2,5-cis-Substituted Piperidines via Suzuki Cross-Coupling

  摘要：

  1,2,3,4-Tetrahydropyridines were halogenated upon treatment with iodine to obtain the desired cross-coupling precursors. Diastereoselective hydrogenation of Suzuki cross-coupling adducts allowed the facile asymmetric synthesis of 2,5-cis-substituted piperidines in five steps from readily available pyridine.

  DOI：

  10.1021/ol061415d

文献信息

• New Methodology Toward Chiral, Non-Racemic 2,5-<i>cis</i>-Substituted Piperidines via Suzuki Cross-Coupling
  作者：Alexandre Larivée、André B. Charette

  DOI：10.1021/ol061415d

  日期：2006.8.1

  1,2,3,4-Tetrahydropyridines were halogenated upon treatment with iodine to obtain the desired cross-coupling precursors. Diastereoselective hydrogenation of Suzuki cross-coupling adducts allowed the facile asymmetric synthesis of 2,5-cis-substituted piperidines in five steps from readily available pyridine.