(2S,1'R)-2,3-dihydro-2-(1',2'-dihydroxy-1'-methylethyl)-7H-furo[3,2-g][1]benzopyran-7-one | 470666-33-2

• 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: (2S,1'R)-2,3-dihydro-2-(1',2'-dihydroxy-1'-methylethyl)-7H-furo[3,2-g][1]benzopyran-7-one
• 英文别名: (2S)-2-[(2R)-1,2-dihydroxypropan-2-yl]-2,3-dihydrofuro[3,2-g]chromen-7-one
• CAS: 470666-33-2
• 化学式: C₁₄H₁₄O₅
• 分子量: 262.262
• InChiKey: JWWIYTKCAJCERS-GXTWGEPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,1'R)-2,3-dihydro-2-(1',2'-dihydroxy-1'-methylethyl)-7H-furo[3,2-g][1]benzopyran-7-one 在 吡啶 、 sodium acetate 作用下， 反应 15.0h， 生成 (2S,1'R)-2,3-dihydro-2-(1',2'-diacetyloxy-1'-methylethyl)-7H-furo[3,2-g][1]benzopyran-7-one
  参考文献：
  名称：

  Synthesis and absolute configuration of the four possible stereoisomers of prandiol

  摘要：

  Prandiol and its three stereoisomers were synthesized in five steps starting either from (R)-(+)-2,3-dihydro-2-(1'-methylethenyl)-6-methoxybenzofuran la or from its enantiomer (S)-(-)-1b. The synthesis involved condensation of the corresponding phenol 4 with ethyl propiolate to afford furocoumarins 6. The absolute configuration of the newly formed stereogenic center at C(1') was established by circular dichroism spectroscopy in combination with X-ray crystallographic analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00267-7
• 作为产物：
  描述：

  异紫花前胡素当归酯 在 氯化亚砜 、 sodium carbonate 、 间氯过氧苯甲酸 作用下， 以 吡啶 、 甲醇 、 苯 为溶剂， 生成 (2S,1'R)-2,3-dihydro-2-(1',2'-dihydroxy-1'-methylethyl)-7H-furo[3,2-g][1]benzopyran-7-one
  参考文献：
  名称：

  Coumarins from Ferulago capillaris and F. brachyloba

  摘要：

  Four new coumarins, (+)-senecioylprangol, (-)-3 '-senecioyloxymarmesin, (+)-3 '-hydroxyprantschimgin and (+)-2"-senecioyloxymarmesin, besides 12 known coumarins have been isolated from two Ferulago species. Their structures have been established by spectroscopic methods and partial synthesis. New synthetic 3'-oxocoumarins are also described. There is a remarkable difference in the contents of the most abundant coumarins found in the roots of both species: osthol and aurapten are specific to F. capillaris and F. brachyloba, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00524-5

文献信息

• Isolation, Total Synthesis, and Relative Stereochemistry of a Dihydrofurocoumarin from <i>Dorstenia contrajerva</i>
  作者：Ricardo Tovar-Miranda、Raúl Cortés-García、Norma F. Santos-Sánchez、Pedro Joseph-Nathan

  DOI：10.1021/np9801209

  日期：1998.10.1

  The roots of Dorstenia contrajerua afforded the dihydrofurocoumarin 1b whose identity was determined from NMR spectral data of the derived acetate 7b combined with the total syntheses of 1a and 1b, which were carried out in five steps with 19% overall yield, starting from 2,3-dihydro-2-isopropenyl-6-methoxybenzofuran (2). The relative stereochemistry of 7b was determined from a single-crystal X-ray diffraction study as(2S*,1'S*)-2,3-dihydro-2-(1'-hydroxy- l'-acetyloxymethylethyl)-7H-furo[3,2g][1]benzopyran-7-one.
• Coumarins from Ferulago capillaris and F. brachyloba
  作者：Benedicto Jiménez、Marı́a Concepción Grande、Josefa Anaya、Pascual Torres、Manuel Grande

  DOI：10.1016/s0031-9422(99)00524-5

  日期：2000.4

  Four new coumarins, (+)-senecioylprangol, (-)-3 '-senecioyloxymarmesin, (+)-3 '-hydroxyprantschimgin and (+)-2"-senecioyloxymarmesin, besides 12 known coumarins have been isolated from two Ferulago species. Their structures have been established by spectroscopic methods and partial synthesis. New synthetic 3'-oxocoumarins are also described. There is a remarkable difference in the contents of the most abundant coumarins found in the roots of both species: osthol and aurapten are specific to F. capillaris and F. brachyloba, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis and absolute configuration of the four possible stereoisomers of prandiol
  作者：Ricardo Tovar-Miranda、Raúl Cortés-Garcı́a、Pedro Joseph-Nathan

  DOI：10.1016/s0957-4166(02)00267-7

  日期：2002.6

  Prandiol and its three stereoisomers were synthesized in five steps starting either from (R)-(+)-2,3-dihydro-2-(1'-methylethenyl)-6-methoxybenzofuran la or from its enantiomer (S)-(-)-1b. The synthesis involved condensation of the corresponding phenol 4 with ethyl propiolate to afford furocoumarins 6. The absolute configuration of the newly formed stereogenic center at C(1') was established by circular dichroism spectroscopy in combination with X-ray crystallographic analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.