(+)-(7S)-7-O-methylsydonic acid | 1313018-91-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+)-(7S)-7-O-methylsydonic acid
• 英文别名: (+)-7-O-methylsydonic acid；3-hydroxy-4-[(2S)-2-methoxy-6-methylheptan-2-yl]benzoic acid
• CAS: 1313018-91-5
• 化学式: C₁₆H₂₄O₄
• 分子量: 280.364
• InChiKey: WVQKVHAEEDYXPI-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2S,3S)-2,3-Epoxy-3,7-dimethyl-1-octanol 在 咪唑 、 四氯化碳 、 4-二甲氨基吡啶 、 manganese(IV) oxide 、 正丁基锂 、 四丁基氟化铵 、 碳酸氢钠 、 三乙胺 、 三苯基膦 、 红铝 、 三氟乙酸酐 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 69.33h， 生成 (+)-(7S)-7-O-methylsydonic acid
  参考文献：
  名称：

  A divergent and stereoselective approach to phenolic 1,7-dihydroxy-bisabolane sesquiterpenes: asymmetric total synthesis of (+)-curcutetraol, (+)-sydonol, (+)-sydonic acid, and (+)-7-O-methylsydonic acid

  摘要：

  The combined use of the Sharpless asymmetric epoxidation, a number of stereospecific chemical transformations, and the 3,5-hexadienoic acid benzannulation protocol allowed us to devise a new, divergent, and stereoselective approach to terpenes with a chiral tertiary hydroxyl group at the ortho-position of a phenol functional group. Accordingly, the natural occurring enantiomeric forms of the bisabolane sesquiterpenes (+)-curcutetraol, (+)-sydonol, (+)-sydonic acid, and (+)-7-O-methylsydonic acid were synthesized with high enantiomeric purity starting from geraniol. The latter two acids were prepared in enantioenriched form for the first time. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.07.011

文献信息

• A divergent and stereoselective approach to phenolic 1,7-dihydroxy-bisabolane sesquiterpenes: asymmetric total synthesis of (+)-curcutetraol, (+)-sydonol, (+)-sydonic acid, and (+)-7-O-methylsydonic acid
  作者：Stefano Serra、Alessandra A. Cominetti

  DOI：10.1016/j.tetasy.2013.07.011

  日期：2013.9

  The combined use of the Sharpless asymmetric epoxidation, a number of stereospecific chemical transformations, and the 3,5-hexadienoic acid benzannulation protocol allowed us to devise a new, divergent, and stereoselective approach to terpenes with a chiral tertiary hydroxyl group at the ortho-position of a phenol functional group. Accordingly, the natural occurring enantiomeric forms of the bisabolane sesquiterpenes (+)-curcutetraol, (+)-sydonol, (+)-sydonic acid, and (+)-7-O-methylsydonic acid were synthesized with high enantiomeric purity starting from geraniol. The latter two acids were prepared in enantioenriched form for the first time. (C) 2013 Elsevier Ltd. All rights reserved.