(-)-(R)-5,7-dimethoxyethoxymethyloxy-2,3-dihydrobenzofuran-2-carbaldehyde | 312608-16-5

• 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: (-)-(R)-5,7-dimethoxyethoxymethyloxy-2,3-dihydrobenzofuran-2-carbaldehyde
• 英文别名: (2R)-5,7-bis(2-methoxyethoxymethoxy)-2,3-dihydro-1-benzofuran-2-carbaldehyde
• CAS: 312608-16-5
• 化学式: C₁₇H₂₄O₈
• 分子量: 356.373
• InChiKey: MDSSHTUCGFMANE-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (E)-(but-2-en-1-yl)triphenylphosphonium bromide 、 (-)-(R)-5,7-dimethoxyethoxymethyloxy-2,3-dihydrobenzofuran-2-carbaldehyde 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 生成 (2R)-5,7-bis(2-methoxyethoxymethoxy)-2-[(1E,3E)-penta-1,3-dienyl]-2,3-dihydro-1-benzofuran
  参考文献：
  名称：

  Enantioselective acylation of 2-hydroxymethyl-2,3-dihydrobenzofurans catalysed by lipase from Pseudomonas cepacia (Amano PS) and total stereoselective synthesis of (−)-(R)-MEM-protected arthrographol

  摘要：

  Lipase Amano PS catalysed acylation of (+/-)-2-hydroxymethyl-2,3-dihydrobenzofurans using vinyl acetate as the acyl donor in n-hexane gave (-)-(R)-2-acetoxymethyl-2,3-dihydrobenzo and (+)-(S)-2-hydroxymethyl-2,3-dihydrobenzofurans in high enantiomeric excess. (-)-(R)-Acetate 18j is converted to (-)-(R)-MEM-protected arthrographol 22. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00302-5
• 作为产物：
  描述：

  (-)-(R)-5,7-dimethoxyethoxymethyloxy-2-acetoxymethyl-2,3-dihydrobenzofuran 在 草酰氯 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (-)-(R)-5,7-dimethoxyethoxymethyloxy-2,3-dihydrobenzofuran-2-carbaldehyde
  参考文献：
  名称：

  Enantioselective acylation of 2-hydroxymethyl-2,3-dihydrobenzofurans catalysed by lipase from Pseudomonas cepacia (Amano PS) and total stereoselective synthesis of (−)-(R)-MEM-protected arthrographol

  摘要：

  Lipase Amano PS catalysed acylation of (+/-)-2-hydroxymethyl-2,3-dihydrobenzofurans using vinyl acetate as the acyl donor in n-hexane gave (-)-(R)-2-acetoxymethyl-2,3-dihydrobenzo and (+)-(S)-2-hydroxymethyl-2,3-dihydrobenzofurans in high enantiomeric excess. (-)-(R)-Acetate 18j is converted to (-)-(R)-MEM-protected arthrographol 22. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00302-5

文献信息

• Enantioselective acylation of 2-hydroxymethyl-2,3-dihydrobenzofurans catalysed by lipase from Pseudomonas cepacia (Amano PS) and total stereoselective synthesis of (−)-(R)-MEM-protected arthrographol
  作者：S Ramadas、G.L.David Krupadanam

  DOI：10.1016/s0957-4166(00)00302-5

  日期：2000.8

  Lipase Amano PS catalysed acylation of (+/-)-2-hydroxymethyl-2,3-dihydrobenzofurans using vinyl acetate as the acyl donor in n-hexane gave (-)-(R)-2-acetoxymethyl-2,3-dihydrobenzo and (+)-(S)-2-hydroxymethyl-2,3-dihydrobenzofurans in high enantiomeric excess. (-)-(R)-Acetate 18j is converted to (-)-(R)-MEM-protected arthrographol 22. (C) 2000 Published by Elsevier Science Ltd.