6-iodo-(8-(2)H)-umbelliferone | 200722-64-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6-iodo-(8-(2)H)-umbelliferone
• CAS: 200722-64-1
• 化学式: C₉H₅IO₃
• 分子量: 289.033
• InChiKey: CEXXLVQOIZYYSU-QYKNYGDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.44
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-iodo-(8-(2)H)-umbelliferone 在 palladium on activated charcoal copper(I) oxide 、 甲酸 、 三乙胺 作用下， 以 吡啶 、 丙酮 为溶剂， 反应 4.0h， 生成 (+/-)-(8,2'',2'',2'',3'',3'',3''-(2)H7)-marmesin
  参考文献：
  名称：

  Stereoselective syntheses of deuterium labelled marmesins; valuable metabolic probes for mechanistic studies in furanocoumarin biosynthesis

  摘要：

  Stereoselective syntheses of deuterium labelled marmesins 3a-3e as metabolic probes for biosynthetic studies are described. Starting from iodo-umbelliferone (5), the title compounds were readily available by copper catalysed alkylation-cyclisation and subsequent transfer-hydrogenation of the resulting furanocoumarins 6a-6e. The bioconversion of marmesin by a microsomal preparation of A. majus yielded psoralene (4) and acetone in a single step and proceeded as a syn-elimination of the alkoxy-substituent together with a single hydrogen atom from a vicinal carbon atom (beta-cleavage). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10237-x
• 作为产物：
  描述：

  6-iodo-7-hydroxycoumarin 在 diclazuril 、 氘代甲醇-d 、 氘代硫酸 作用下， 生成 6-iodo-(8-(2)H)-umbelliferone
  参考文献：
  名称：

  Stereoselective syntheses of deuterium labelled marmesins; valuable metabolic probes for mechanistic studies in furanocoumarin biosynthesis

  摘要：

  Stereoselective syntheses of deuterium labelled marmesins 3a-3e as metabolic probes for biosynthetic studies are described. Starting from iodo-umbelliferone (5), the title compounds were readily available by copper catalysed alkylation-cyclisation and subsequent transfer-hydrogenation of the resulting furanocoumarins 6a-6e. The bioconversion of marmesin by a microsomal preparation of A. majus yielded psoralene (4) and acetone in a single step and proceeded as a syn-elimination of the alkoxy-substituent together with a single hydrogen atom from a vicinal carbon atom (beta-cleavage). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10237-x

文献信息

• Stereoselective syntheses of deuterium labelled marmesins; valuable metabolic probes for mechanistic studies in furanocoumarin biosynthesis
  作者：Volker Stanjek、Martin Miksch、Wilhelm Boland

  DOI：10.1016/s0040-4020(97)10237-x

  日期：1997.12

  Stereoselective syntheses of deuterium labelled marmesins 3a-3e as metabolic probes for biosynthetic studies are described. Starting from iodo-umbelliferone (5), the title compounds were readily available by copper catalysed alkylation-cyclisation and subsequent transfer-hydrogenation of the resulting furanocoumarins 6a-6e. The bioconversion of marmesin by a microsomal preparation of A. majus yielded psoralene (4) and acetone in a single step and proceeded as a syn-elimination of the alkoxy-substituent together with a single hydrogen atom from a vicinal carbon atom (beta-cleavage). (C) 1997 Elsevier Science Ltd.