(5S,12R)-5-(methoxymethoxy)-12-methyl-1-oxa-3-cyclododecen-2-one | 1239349-05-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (5S,12R)-5-(methoxymethoxy)-12-methyl-1-oxa-3-cyclododecen-2-one
• 英文别名: (3E,5S,12R)-5-(methoxymethoxy)-12-methyl-1-oxacyclododec-3-en-2-one
• CAS: 1239349-05-3
• 化学式: C₁₄H₂₄O₄
• 分子量: 256.342
• InChiKey: LQFNQTJMLOKLCP-GBYBRZQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S,12R)-5-(methoxymethoxy)-12-methyl-1-oxa-3-cyclododecen-2-one 在 cerium(III) chloride 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 48.0h， 以60%的产率得到(5S,12R)-5-hydroxyy-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-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

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.