(2R,1'S)-2,3-dihydro-2-(1',2'-dihydroxy-1'-methylethyl)-7H-furo[3,2-g][1]benzopyran-7-one | 470666-28-5

• 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: (2R,1'S)-2,3-dihydro-2-(1',2'-dihydroxy-1'-methylethyl)-7H-furo[3,2-g][1]benzopyran-7-one
• 英文别名: (2R)-2-[(2S)-1,2-dihydroxypropan-2-yl]-2,3-dihydrofuro[3,2-g]chromen-7-one
• CAS: 470666-28-5
• 化学式: C₁₄H₁₄O₅
• 分子量: 262.262
• InChiKey: JWWIYTKCAJCERS-OCCSQVGLSA-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：

  (2R,1'S)-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 (2R,1'S)-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：

  (2R,1'S)-2,3-dihydro-2-(2',2',4'-trimethyl-1',3'-dioxolan-4'-yl)-7H-furo[3,2-g][1]benzopyran-7-one 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以97%的产率得到(2R,1'S)-2,3-dihydro-2-(1',2'-dihydroxy-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

文献信息

• 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.