3-(3-phenyl-1R,2S-dihydroxypropyl)-1,5-dihydro-3H-2,4-benzodioxepine | 153230-44-5

• 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: 3-(3-phenyl-1R,2S-dihydroxypropyl)-1,5-dihydro-3H-2,4-benzodioxepine
• 英文别名: (1R,2S)-1-(1,5-dihydro-2,4-benzodioxepin-3-yl)-2-phenylethane-1,2-diol
• CAS: 153230-44-5
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: NGLLSZLJJZMEHZ-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3-phenyl-1R,2S-dihydroxypropyl)-1,5-dihydro-3H-2,4-benzodioxepine 在 KCl-HCl buffer 作用下， 反应 10.0h， 生成 (2R,3S)-2,3-dihydroxy-3-phenylpropanal
  参考文献：
  名称：

  Synthesis of carbohydrates via tandem use of the osmium-catalyzed asymmetric dihydroxylation and enzyme-catalyzed aldol addition reactions

  摘要：

  A new strategy is described for the asymmetric synthesis of carbohydrate derivatives via the tandem use of the osmium-catalyzed asymmetric dihydroxylation (AD) and aldolase-catalyzed aldol addition reactions. Both D- and L-forms of fructose, 6-deoxy-galacto-2-heptulose, and 6-phenyl-galacto-2-hexulose were synthesized to illustrate this methodology.

  DOI：

  10.1021/ja00081a016
• 作为产物：
  描述：

  邻苯二甲醇 在 AD-mix-α 、 甲基磺酰胺 、 对甲苯磺酸 作用下， 以 乙二醇二甲醚 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 71.0h， 生成 3-(3-phenyl-1R,2S-dihydroxypropyl)-1,5-dihydro-3H-2,4-benzodioxepine
  参考文献：
  名称：

  Synthesis of carbohydrates via tandem use of the osmium-catalyzed asymmetric dihydroxylation and enzyme-catalyzed aldol addition reactions

  摘要：

  A new strategy is described for the asymmetric synthesis of carbohydrate derivatives via the tandem use of the osmium-catalyzed asymmetric dihydroxylation (AD) and aldolase-catalyzed aldol addition reactions. Both D- and L-forms of fructose, 6-deoxy-galacto-2-heptulose, and 6-phenyl-galacto-2-hexulose were synthesized to illustrate this methodology.

  DOI：

  10.1021/ja00081a016

文献信息

• Synthesis of carbohydrates via tandem use of the osmium-catalyzed asymmetric dihydroxylation and enzyme-catalyzed aldol addition reactions
  作者：Ian Henderson、K. Barry Sharpless、Chi Huey Wong

  DOI：10.1021/ja00081a016

  日期：1994.1

  A new strategy is described for the asymmetric synthesis of carbohydrate derivatives via the tandem use of the osmium-catalyzed asymmetric dihydroxylation (AD) and aldolase-catalyzed aldol addition reactions. Both D- and L-forms of fructose, 6-deoxy-galacto-2-heptulose, and 6-phenyl-galacto-2-hexulose were synthesized to illustrate this methodology.