(2S,1'S)-2,3-dihydro-2-(2',2',4'-trimethyl-1',3'-dioxolan-4'-yl)-6-methoxybenzofuran | 470459-93-9

• 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'S)-2,3-dihydro-2-(2',2',4'-trimethyl-1',3'-dioxolan-4'-yl)-6-methoxybenzofuran
• 英文别名: (2S)-6-methoxy-2-[(4S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-2,3-dihydro-1-benzofuran
• CAS: 470459-93-9
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: JJGGEXFIQPQBMR-ZFWWWQNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

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)-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'S)-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
• 作为产物：
  描述：

  (S)-(-)-2,3-dihydro-2-(1'-methylethenyl)-6-methoxybenzofuran 在 AD-mix-α 、 水 、 对甲苯磺酸 作用下， 以 叔丁醇 为溶剂， 生成 (2S,1'S)-2,3-dihydro-2-(2',2',4'-trimethyl-1',3'-dioxolan-4'-yl)-6-methoxybenzofuran
  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

• 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.
• 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.