6-bromo-2-methyl-1,3-benzodioxin | 189684-10-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 6-bromo-2-methyl-1,3-benzodioxin
• 英文别名: 6-bromo-2-methyl-4H-1,3-benzodioxine
• CAS: 189684-10-4
• 化学式: C₉H₉BrO₂
• 分子量: 229.073
• InChiKey: INNPCXMQFHTCTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-bromo-2-methyl-1,3-benzodioxin 在 扁桃腈裂解酶来源于杏仁 、 magnesium 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 、 异丙醚 为溶剂， 反应 34.0h， 生成 (R)-Hydroxy-(2-methyl-4H-benzo[1,3]dioxin-6-yl)-acetonitrile
  参考文献：
  名称：

  Synthesis of the Adrenergic Bronchodilators (R)-Terbutaline and (R)-Salbutamol from (R)-Cyanohydrins¹

  摘要：

  Stereoselective syntheses of (R)-terbutaline and (R)-salbutamol acetal, which are important bronchodilators, starting from O-protected (R)-cyanohydrins are described. (R)-Terbutaline hydrochloride (R)-9.HCl is obtained in an overall yield of 44% with >98% ee from the O-bisallyl-protected cyanohydrin (R)-4k via a Ritter N-tertiary butylation to the amide (R)-6a, hydrogenation to the amino alcohol (R)-7a, and deprotection of the hydroxyl functions. (R)-Salbutamol acetals (R)-7b,c can be obtained from the corresponding O-protected (R)-cyanohydrins either via the route described for (R)-terbutaline or via selective hydrogenation of the protected cyanohydrin (R)-11 to the imino derivative, transimination with tert-butylamine, followed by hydrogenation with NaBH4 to give the 2-amino alcohol derivative (R)-12. Desilylation of(R)-12 to (R)-7c is performed with LiAlH4. Hydrolytic cleavage of the acetals (R)-7b and c to (R)-salbutamol was not yet possible without racemization.

  DOI：

  10.1021/jo970032d
• 作为产物：
  描述：

  5-溴-2-羟基苯甲醇 、 乙烯基乙醚 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 以92%的产率得到6-bromo-2-methyl-1,3-benzodioxin
  参考文献：
  名称：

  Synthesis of the Adrenergic Bronchodilators (R)-Terbutaline and (R)-Salbutamol from (R)-Cyanohydrins¹

  摘要：

  Stereoselective syntheses of (R)-terbutaline and (R)-salbutamol acetal, which are important bronchodilators, starting from O-protected (R)-cyanohydrins are described. (R)-Terbutaline hydrochloride (R)-9.HCl is obtained in an overall yield of 44% with >98% ee from the O-bisallyl-protected cyanohydrin (R)-4k via a Ritter N-tertiary butylation to the amide (R)-6a, hydrogenation to the amino alcohol (R)-7a, and deprotection of the hydroxyl functions. (R)-Salbutamol acetals (R)-7b,c can be obtained from the corresponding O-protected (R)-cyanohydrins either via the route described for (R)-terbutaline or via selective hydrogenation of the protected cyanohydrin (R)-11 to the imino derivative, transimination with tert-butylamine, followed by hydrogenation with NaBH4 to give the 2-amino alcohol derivative (R)-12. Desilylation of(R)-12 to (R)-7c is performed with LiAlH4. Hydrolytic cleavage of the acetals (R)-7b and c to (R)-salbutamol was not yet possible without racemization.

  DOI：

  10.1021/jo970032d

文献信息

• A general route to pyridine-modified salicylaldehydes via Suzuki coupling
  作者：Gregory A. Morris、SonBinh T. Nguyen

  DOI：10.1016/s0040-4039(01)00106-x

  日期：2001.3

  An efficient method for the preparation of 5-(3-pyridyl)- and 5-(4-pyridyl)salicylaldehydes by the palladium-catalyzed cross-coupling reaction of either 4-pyridylboronic acid or diethyl-(3-pyridyl)borane and bromosalicylaldehydes is described. (C) 2001 Published by Elsevier Science Ltd.
• COMPOSITION FOR FORMING SILICON-CONTAINING RESIST UNDERLAYER FILM, PATTERNING PROCESS, AND SILICON COMPOUND
  申请人：SHIN-ETSU CHEMICAL CO., LTD.

  公开号：US20220221793A1

  公开（公告）日：2022-07-14

  The present invention is a composition for forming a silicon-containing resist underlayer film, containing one or both of a hydrolysis product and a hydrolysis condensate of one or more silicon compounds (A-1) shown by the following general formula (1). This provides: a composition for forming a silicon-containing resist underlayer film with which it is possible to form a resist underlayer film having favorable adhesiveness to resist patterns regardless of whether in negative development or positive development, and also having favorable adhesiveness to finer patterns as in EUV photo-exposure; a patterning process; and a silicon compound.
• Synthesis of the Adrenergic Bronchodilators (<i>R</i>)-Terbutaline and (<i>R</i>)-Salbutamol from (<i>R</i>)-Cyanohydrins¹
  作者：Franz Effenberger、Jürgen Jäger

  DOI：10.1021/jo970032d

  日期：1997.6.13

  Stereoselective syntheses of (R)-terbutaline and (R)-salbutamol acetal, which are important bronchodilators, starting from O-protected (R)-cyanohydrins are described. (R)-Terbutaline hydrochloride (R)-9.HCl is obtained in an overall yield of 44% with >98% ee from the O-bisallyl-protected cyanohydrin (R)-4k via a Ritter N-tertiary butylation to the amide (R)-6a, hydrogenation to the amino alcohol (R)-7a, and deprotection of the hydroxyl functions. (R)-Salbutamol acetals (R)-7b,c can be obtained from the corresponding O-protected (R)-cyanohydrins either via the route described for (R)-terbutaline or via selective hydrogenation of the protected cyanohydrin (R)-11 to the imino derivative, transimination with tert-butylamine, followed by hydrogenation with NaBH4 to give the 2-amino alcohol derivative (R)-12. Desilylation of(R)-12 to (R)-7c is performed with LiAlH4. Hydrolytic cleavage of the acetals (R)-7b and c to (R)-salbutamol was not yet possible without racemization.