(2S,1'R)-2,3-dihydro-2-(2',2',4'-trimethyl-1',3'-dioxolan-4'-yl)-6-hydroxybenzofuran | 470459-95-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: (2S,1'R)-2,3-dihydro-2-(2',2',4'-trimethyl-1',3'-dioxolan-4'-yl)-6-hydroxybenzofuran
• 英文别名: (2S)-2-[(4R)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-2,3-dihydro-1-benzofuran-6-ol
• CAS: 470459-95-1
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: FHYUGFDDMWOMEZ-GXTWGEPZSA-N

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：
  0.57
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  丙炔酸乙酯 、 (2S,1'R)-2,3-dihydro-2-(2',2',4'-trimethyl-1',3'-dioxolan-4'-yl)-6-hydroxybenzofuran 以36%的产率得到(2S,1'R)-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
• 作为产物：
  描述：

  (2S,1'R)-2,3-dihydro-2-(2',2',4'-trimethyl-1',3'-dioxolan-4'-yl)-6-methoxybenzofuran 在 硫代乙氧基锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以81%的产率得到(2S,1'R)-2,3-dihydro-2-(2',2',4'-trimethyl-1',3'-dioxolan-4'-yl)-6-hydroxybenzofuran
  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.