nodachenetin | 28664-60-0

• 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: nodachenetin
• 英文别名: 7H-Furo[3,2-g][1]benzopyran-7-one, 2-(1-hydroxy-1-methylethyl)-；2-(2-hydroxypropan-2-yl)furo[3,2-g]chromen-7-one
• CAS: 28664-60-0
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: QITAPBJXOHCHQR-UHFFFAOYSA-N

物化性质

• 沸点：
  444.1±40.0 °C(Predicted)
• 密度：
  1.344±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  nodachenetin 在 palladium on activated charcoal 甲酸-d2 、 三乙胺 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以58%的产率得到(+/-)-trans-(2',3'-(2)H2)-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：

  7-甲氧基香豆素 在 吡啶 、 copper(I) oxide 、 ammonium hydroxide 、 碘 、 sodium methylate 、 三溴化硼 、 potassium iodide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 46.0h， 生成 nodachenetin
  参考文献：
  名称：

  An efficient synthesis of furanocoumarins

  摘要：

  An efficient synthesis of linear and angular furanocoumarins has been carried out starting from iodoumbelliferone derivatives. First synthesis of 6-iodoumbelliferone is described. The average yields are higher than those reported before.

  DOI：

  10.1016/s0040-4020(01)92200-8

文献信息

• King et al., Journal of the Chemical Society, 1954, p. 1392,1395
  作者：King et al.

  DOI：——

  日期：——
• An efficient synthesis of furanocoumarins
  作者：Eva Zubía、Francisco Rodríguez Luis、Guillermo M. Massanet、Isidro G. Collado

  DOI：10.1016/s0040-4020(01)92200-8

  日期：1992.1

  An efficient synthesis of linear and angular furanocoumarins has been carried out starting from iodoumbelliferone derivatives. First synthesis of 6-iodoumbelliferone is described. The average yields are higher than those reported before.
• 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.