Toluene-4-sulfonic acid (1S,3S,4S)-4-hydroxy-8-methoxy-1,3-dimethyl-isochroman-5-yl ester | 714962-26-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Toluene-4-sulfonic acid (1S,3S,4S)-4-hydroxy-8-methoxy-1,3-dimethyl-isochroman-5-yl ester
• CAS: 714962-26-2
• 化学式: C₁₉H₂₂O₆S
• 分子量: 378.446
• InChiKey: UTANWUKVDYUYFW-WTOJCKNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  82.06
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid (1S,3S,4S)-4-hydroxy-8-methoxy-1,3-dimethyl-isochroman-5-yl ester 在 氢氧化钾 、 水 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以84%的产率得到(1S,3S,4S)-8-methoxy-1,3-dimethyl-3,4-dihydro-1H-isochromene-4,5-diol
  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：

  2-[(1S,2S)-2-(1-Ethoxy-ethoxy)-1-hydroxy-propyl]-4-methoxy-phenol 在 乙缩醛 、 camphor-10-sulfonic acid 、 四氯化钛 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 7.0h， 生成 Toluene-4-sulfonic acid (1S,3S,4S)-4-hydroxy-8-methoxy-1,3-dimethyl-isochroman-5-yl ester
  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

• The Diastereoselective Syntheses of Enantiopure Benzo- and Naphtho-pyrans Related to the Aphid Insect Pigments
  作者：Robin G. F. Giles

  DOI：10.1071/ch03286

  日期：——

  quinone A′, natural derivatives of the aphid insect pigments protoaphin-fb and protoaphin-sl. These are achieved through intramolecular diastereoselective cyclization of tethered phenolic lactaldehydes. The conformational implications of the cyclization process are discussed. Model reactions allow the formulation of a more concise, convergent route to these natural derivatives through the corresponding

  概述了针对对映体纯醌 A 和醌 A'（蚜虫色素 protoaphin-fb 和 protoaphin-sl 的天然衍生物）组装的合成努力。这些是通过束缚酚醛乳醛的分子内非对映选择性环化来实现的。讨论了环化过程的构象含义。模型反应允许通过相应的分子间反应为这些天然衍生物制定更简洁、收敛的路线，其中所需的互补非对映选择性是通过选择苯酚钛或镁与乙氧基乙基保护的不对称乳醛反应来提供的。