6-bromo-3-methylbenzo[d]thiazole-2,4,7(3H)-trione | 1361383-44-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-bromo-3-methylbenzo[d]thiazole-2,4,7(3H)-trione
• 英文别名: 6-Bromo-3-methyl-1,3-benzothiazole-2,4,7-trione
• CAS: 1361383-44-9
• 化学式: C₈H₄BrNO₃S
• 分子量: 274.095
• InChiKey: KPUUVOLJEAQVTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  79.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-bromo-3-methylbenzo[d]thiazole-2,4,7(3H)-trione 在 silver(II) oxide 、 硝酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 cis-5-hydroxy-8-(2-hydroxyethyl)-6-isopentyl-1-methyl-8,9-dihydro-1H-pyrano[3',4':6,7]naphtho[2,3-d]thiazole-2,4,11(6H)-trione
  参考文献：
  名称：

  Total Synthesis of Mevashuntin

  摘要：

  The total synthesis of (+/-)-mevashuntin, a structurally unique naturally occurring pyrano-naphthoquinone-thiazolone, is described. The route is centered upon a late stage regioselective Diels-Alder reaction between two highly functionalized components, as well as an improved protocol for the one pot synthesis of benzothiazolones from ortho-bromoaryl isothiocyanates. The strategy results in a highly convergent route, providing access to the natural product in 11 steps from 3-(4-methoxyphenoxy)propanol and confirming its relative stereochemistry.

  DOI：

  10.1021/ol300221e
• 作为产物：
  描述：

  2,5-二甲氧基苯胺 在 盐酸 、 copper(l) iodide 、 1,10-菲罗啉 、 ammonium cerium (IV) nitrate 、 乙醇 、 水 、 溴 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 66.08h， 生成 6-bromo-3-methylbenzo[d]thiazole-2,4,7(3H)-trione
  参考文献：
  名称：

  Total Synthesis of Mevashuntin

  摘要：

  The total synthesis of (+/-)-mevashuntin, a structurally unique naturally occurring pyrano-naphthoquinone-thiazolone, is described. The route is centered upon a late stage regioselective Diels-Alder reaction between two highly functionalized components, as well as an improved protocol for the one pot synthesis of benzothiazolones from ortho-bromoaryl isothiocyanates. The strategy results in a highly convergent route, providing access to the natural product in 11 steps from 3-(4-methoxyphenoxy)propanol and confirming its relative stereochemistry.

  DOI：

  10.1021/ol300221e

文献信息

• Total Synthesis of Mevashuntin
  作者：Christopher C. Nawrat、Christopher J. Moody

  DOI：10.1021/ol300221e

  日期：2012.3.16

  The total synthesis of (+/-)-mevashuntin, a structurally unique naturally occurring pyrano-naphthoquinone-thiazolone, is described. The route is centered upon a late stage regioselective Diels-Alder reaction between two highly functionalized components, as well as an improved protocol for the one pot synthesis of benzothiazolones from ortho-bromoaryl isothiocyanates. The strategy results in a highly convergent route, providing access to the natural product in 11 steps from 3-(4-methoxyphenoxy)propanol and confirming its relative stereochemistry.