(1R)-2-{2-[(S)-4-isopropyl-4,5-dihydrooxazol-2-yl]-3-methoxyphenyl}-1-(4-methoxy-3-(methoxymethoxy)phenyl)ethanol | 946001-97-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1R)-2-{2-[(S)-4-isopropyl-4,5-dihydrooxazol-2-yl]-3-methoxyphenyl}-1-(4-methoxy-3-(methoxymethoxy)phenyl)ethanol
• 英文别名: (1R)-1-[4-methoxy-3-(methoxymethoxy)phenyl]-2-[3-methoxy-2-[(4S)-4-propan-2-yl-4,5-dihydro-1,3-oxazol-2-yl]phenyl]ethanol
• CAS: 946001-97-4
• 化学式: C₂₄H₃₁NO₆
• 分子量: 429.513
• InChiKey: KAAZJIKYNZYKLW-RTBURBONSA-N

物化性质

• 沸点：
  575.3±50.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  78.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1R)-2-{2-[(S)-4-isopropyl-4,5-dihydrooxazol-2-yl]-3-methoxyphenyl}-1-(4-methoxy-3-(methoxymethoxy)phenyl)ethanol 在 盐酸 、 silica gel 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 116.0h， 生成 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 、 三乙胺 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 环己烷 为溶剂， 反应 1.0h， 生成 (1R)-2-{2-[(S)-4-isopropyl-4,5-dihydrooxazol-2-yl]-3-methoxyphenyl}-1-(4-methoxy-3-(methoxymethoxy)phenyl)ethanol
  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.