(R)-8-hydroxy-3-(4-methoxy-3-(methoxymethoxy)phenyl)-3,4-dihydroisocoumarin | 946002-05-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (R)-8-hydroxy-3-(4-methoxy-3-(methoxymethoxy)phenyl)-3,4-dihydroisocoumarin
• 英文别名: (3R)-8-hydroxy-3-[4-methoxy-3-(methoxymethoxy)phenyl]-3,4-dihydroisochromen-1-one
• CAS: 946002-05-7
• 化学式: C₁₈H₁₈O₆
• 分子量: 330.337
• InChiKey: DZWRFCCOBNCUNT-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-8-hydroxy-3-(4-methoxy-3-(methoxymethoxy)phenyl)-3,4-dihydroisocoumarin 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以100%的产率得到白花前胡甲素
  参考文献：
  名称：

  Asymmetric synthesis of 3-substituted 8-hydroxy-3,4-dihydroisocoumarins from (S)-4-isopropyl-2-(2-methoxy-6-methylphenyl)oxazoline

  摘要：

  Reaction of the laterally lithiated (S)-4-isopropyl-2-(2-methoxy-6-methylphenyl) oxazoline with p-tolualdehyde gave an inseparable mixture of the addition products in low diastereoselectivity. However, the (S, S)-product cyclized to the corresponding 3,4-dihydroisocoumarin faster than the (S, R)-product on silica gel, which allowed to be produced both enantiomers of 8-methoxy-3-(p-tolyl)-3,4-dihydroisocoumarin in moderate to good optical purity [S-enantiomer: 75% ee; R-enantiomer: 96% ee]. This procedure was applied to the short-step synthesis of optically active 3,4-dihydroisocoumarin natural products such as (R)-8-hydroxy-3-(1-tridecyl)-3,4-dihydroisocoumarin and (R)-phyllodulcin. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.092
• 作为产物：
  描述：

  2-甲氧基-6-甲基苯甲酰氯 在 仲丁基锂 、 silica gel 、 三乙胺 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 环己烷 为溶剂， 反应 114.0h， 生成 (R)-8-hydroxy-3-(4-methoxy-3-(methoxymethoxy)phenyl)-3,4-dihydroisocoumarin
  参考文献：
  名称：

  Asymmetric synthesis of 3-substituted 8-hydroxy-3,4-dihydroisocoumarins from (S)-4-isopropyl-2-(2-methoxy-6-methylphenyl)oxazoline

  摘要：

  Reaction of the laterally lithiated (S)-4-isopropyl-2-(2-methoxy-6-methylphenyl) oxazoline with p-tolualdehyde gave an inseparable mixture of the addition products in low diastereoselectivity. However, the (S, S)-product cyclized to the corresponding 3,4-dihydroisocoumarin faster than the (S, R)-product on silica gel, which allowed to be produced both enantiomers of 8-methoxy-3-(p-tolyl)-3,4-dihydroisocoumarin in moderate to good optical purity [S-enantiomer: 75% ee; R-enantiomer: 96% ee]. This procedure was applied to the short-step synthesis of optically active 3,4-dihydroisocoumarin natural products such as (R)-8-hydroxy-3-(1-tridecyl)-3,4-dihydroisocoumarin and (R)-phyllodulcin. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.092

文献信息

• Asymmetric synthesis of 3-substituted 8-hydroxy-3,4-dihydroisocoumarins from (S)-4-isopropyl-2-(2-methoxy-6-methylphenyl)oxazoline
  作者：Katsuya Uchida、Tsutomu Fukuda、Masatomo Iwao

  DOI：10.1016/j.tet.2007.04.092

  日期：2007.7

  Reaction of the laterally lithiated (S)-4-isopropyl-2-(2-methoxy-6-methylphenyl) oxazoline with p-tolualdehyde gave an inseparable mixture of the addition products in low diastereoselectivity. However, the (S, S)-product cyclized to the corresponding 3,4-dihydroisocoumarin faster than the (S, R)-product on silica gel, which allowed to be produced both enantiomers of 8-methoxy-3-(p-tolyl)-3,4-dihydroisocoumarin in moderate to good optical purity [S-enantiomer: 75% ee; R-enantiomer: 96% ee]. This procedure was applied to the short-step synthesis of optically active 3,4-dihydroisocoumarin natural products such as (R)-8-hydroxy-3-(1-tridecyl)-3,4-dihydroisocoumarin and (R)-phyllodulcin. (C) 2007 Elsevier Ltd. All rights reserved.