2-[(1R,2S)-2-(1-ethoxyethoxy)-1-hydroxypropyl]-4-methoxyphenol | 714962-19-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-[(1R,2S)-2-(1-ethoxyethoxy)-1-hydroxypropyl]-4-methoxyphenol
• CAS: 714962-19-3
• 化学式: C₁₄H₂₂O₅
• 分子量: 270.326
• InChiKey: NBWFUGUXYKLIBO-GEPZPADCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(1R,2S)-2-(1-ethoxyethoxy)-1-hydroxypropyl]-4-methoxyphenol 在 乙缩醛 、 氢氧化钾 、 camphor-10-sulfonic acid 、 水 、 四氯化钛 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 13.5h， 生成 (1S,3S,4R)-3,4-Dihydro-4,5-dihydroxy-1,3-dimethyl-8-methoxy-2-benzopyran
  参考文献：
  名称：

  Short, convergent, stereoselective syntheses of enantiopure 2-benzopyran-5,8-quinones related to the aphid insect pigments, the protoaphins

  摘要：

  The enantiopure (1S,3S,4R)-, (1R,3S,4S)- and (1S,3S,4S)-3,4-dihydro-1,3-dimethyl-4-hydroxy-2-benzopyrans 16, 25 and 26 are prepared in two related reaction sequences, each in eight steps and good overall yield. The starting materials are 4-methoxyphenol 6 and (2S, 1'R and 2S, 1'S)-1' ethoxyethoxypropanal 9, the latter providing the source of asymmetry from the chiral pool. The three key reactions involved in each sequence are either highly or completely diastereoselective. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.065
• 作为产物：
  描述：

  (S)-2(1-ethoxyethoxy)propanal 、 4-甲氧基苯酚 在 titanium(IV) isopropylate 作用下， 以 甲苯 为溶剂， 反应 5.33h， 生成 2-[(1S,2S)-2-(1-Ethoxy-ethoxy)-1-hydroxy-propyl]-4-methoxy-phenol 、 2-[(1R,2S)-2-(1-ethoxyethoxy)-1-hydroxypropyl]-4-methoxyphenol
  参考文献：
  名称：

  Short, convergent, stereoselective syntheses of enantiopure 2-benzopyran-5,8-quinones related to the aphid insect pigments, the protoaphins

  摘要：

  The enantiopure (1S,3S,4R)-, (1R,3S,4S)- and (1S,3S,4S)-3,4-dihydro-1,3-dimethyl-4-hydroxy-2-benzopyrans 16, 25 and 26 are prepared in two related reaction sequences, each in eight steps and good overall yield. The starting materials are 4-methoxyphenol 6 and (2S, 1'R and 2S, 1'S)-1' ethoxyethoxypropanal 9, the latter providing the source of asymmetry from the chiral pool. The three key reactions involved in each sequence are either highly or completely diastereoselective. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.065

文献信息

• Short, convergent, stereoselective syntheses of enantiopure 2-benzopyran-5,8-quinones related to the aphid insect pigments, the protoaphins
  作者：Anthony A Birkbeck、Zinka Brkic、Robin G.F Giles

  DOI：10.1016/j.tetlet.2004.06.065

  日期：2004.8

  The enantiopure (1S,3S,4R)-, (1R,3S,4S)- and (1S,3S,4S)-3,4-dihydro-1,3-dimethyl-4-hydroxy-2-benzopyrans 16, 25 and 26 are prepared in two related reaction sequences, each in eight steps and good overall yield. The starting materials are 4-methoxyphenol 6 and (2S, 1'R and 2S, 1'S)-1' ethoxyethoxypropanal 9, the latter providing the source of asymmetry from the chiral pool. The three key reactions involved in each sequence are either highly or completely diastereoselective. (C) 2004 Elsevier Ltd. All rights reserved.