(2S,1'S)-2,3-dihydro-2-(2',2',4'-trimethyl-1',3'-dioxolan-4'-yl)-7H-furo[3,2-g][1]benzopyran-7-one | 470459-98-4

• 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'S)-2,3-dihydro-2-(2',2',4'-trimethyl-1',3'-dioxolan-4'-yl)-7H-furo[3,2-g][1]benzopyran-7-one
• 英文别名: (2S)-2-[(4S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-2,3-dihydrofuro[3,2-g]chromen-7-one
• CAS: 470459-98-4
• 化学式: C₁₇H₁₈O₅
• 分子量: 302.327
• InChiKey: ARJXRZIQTAFHOH-YOEHRIQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,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92%的产率得到(2S,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
• 作为产物：
  描述：

  丙炔酸乙酯 、 (2S,1'S)-2,3-dihydro-2-(2',2',4'-trimethyl-1',3'-dioxolan-4'-yl)-6-hydroxybenzofuran 以35%的产率得到(2S,1'S)-2,3-dihydro-2-(2',2',4'-trimethyl-1',3'-dioxolan-4'-yl)-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.