(E,4S,11R)-11-hydroxy-4-(methoxymethoxy)-2-dodecenoic acid | 1239349-04-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (E,4S,11R)-11-hydroxy-4-(methoxymethoxy)-2-dodecenoic acid
• 英文别名: (E,4S,11R)-11-hydroxy-4-(methoxymethoxy)dodec-2-enoic acid
• CAS: 1239349-04-2
• 化学式: C₁₄H₂₆O₅
• 分子量: 274.357
• InChiKey: GHOMKWRWPIAHIH-GBYBRZQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E,4S,11R)-11-hydroxy-4-(methoxymethoxy)-2-dodecenoic acid 在 2,4,6-三氯苯甲酰氯 、 三乙胺 、 4-二甲氨基吡啶 作用下， 以 甲苯 为溶剂， 以70%的产率得到(5S,12R)-5-(methoxymethoxy)-12-methyl-1-oxa-3-cyclododecen-2-one
  参考文献：
  名称：

  Enantioselective synthesis of (+)-patulolide C via proline-catalyzed sequential α-aminooxylation and Horner–Wadsworth–Emmons olefination

  摘要：

  The enantioselective total synthesis of (+)-patulolide C isolated from Penicillium urticae has been achieved from commercially available 9-decen-1-ol. Jacobsen's kinetic resolution and sequential alpha-aminooxylation and Horner-Wadsworth-Emmons (HWE) olefination followed by Yamaguchi lactonization are used as the key reaction steps. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.063
• 作为产物：
  描述：

  (E,4S,11R)-11-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-4-(methoxymethoxy)-2-dodecenoic acid 在 水 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以68%的产率得到(E,4S,11R)-11-hydroxy-4-(methoxymethoxy)-2-dodecenoic acid
  参考文献：
  名称：

  Enantioselective synthesis of (+)-patulolide C via proline-catalyzed sequential α-aminooxylation and Horner–Wadsworth–Emmons olefination

  摘要：

  The enantioselective total synthesis of (+)-patulolide C isolated from Penicillium urticae has been achieved from commercially available 9-decen-1-ol. Jacobsen's kinetic resolution and sequential alpha-aminooxylation and Horner-Wadsworth-Emmons (HWE) olefination followed by Yamaguchi lactonization are used as the key reaction steps. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.063

文献信息

• Enantioselective synthesis of (+)-patulolide C via proline-catalyzed sequential α-aminooxylation and Horner–Wadsworth–Emmons olefination
  作者：Gowravaram Sabitha、G. Chandrashekhar、K. Yadagiri、J.S. Yadav

  DOI：10.1016/j.tetlet.2010.05.063

  日期：2010.7

  The enantioselective total synthesis of (+)-patulolide C isolated from Penicillium urticae has been achieved from commercially available 9-decen-1-ol. Jacobsen's kinetic resolution and sequential alpha-aminooxylation and Horner-Wadsworth-Emmons (HWE) olefination followed by Yamaguchi lactonization are used as the key reaction steps. (C) 2010 Elsevier Ltd. All rights reserved.