(R)-2-hydroxy-1-(methoxymethoxy)tridecan-7-one | 950826-51-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-2-hydroxy-1-(methoxymethoxy)tridecan-7-one
• 英文别名: (2R)-2-hydroxy-1-(methoxymethoxy)tridecan-7-one
• CAS: 950826-51-4
• 化学式: C₁₅H₃₀O₄
• 分子量: 274.401
• InChiKey: OEGAIVYWIJSLKA-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-hydroxy-1-(methoxymethoxy)tridecan-7-one 在 三乙基硅烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以79%的产率得到(2S^*,7S^*)-2-hexyl-7-hydroxymethyloxepane
  参考文献：
  名称：

  Enantioselective synthesis of α-benzyloxy-ω-alkenals: application to the synthesis of (+)-exo-brevicomin, (+)-iso-exo-brevicomin, and (−)-isolaurepan

  摘要：

  The enantioselective synthesis of alpha-benzyloxy aldehydes containing a terminal alkene was carried out from chiral Pool L-(+)tartaric acid by employing the stereoselective reduction of a 1,4-diketone as the key step. The synthetic utility of these aldehydes was demonstrated in the synthesis of pine beetle pheromones (+)-exo-brevicomin, (+)-iso-exo-brevicomin and a formal synthesis of 2,7cis-disubstituted oxepane (-)-isolaurepan. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.05.014
• 作为产物：
  描述：

  (R)-2-benzyloxy-1-(methoxymethoxy)tridecan-7-one 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以97%的产率得到(R)-2-hydroxy-1-(methoxymethoxy)tridecan-7-one
  参考文献：
  名称：

  Enantioselective synthesis of α-benzyloxy-ω-alkenals: application to the synthesis of (+)-exo-brevicomin, (+)-iso-exo-brevicomin, and (−)-isolaurepan

  摘要：

  The enantioselective synthesis of alpha-benzyloxy aldehydes containing a terminal alkene was carried out from chiral Pool L-(+)tartaric acid by employing the stereoselective reduction of a 1,4-diketone as the key step. The synthetic utility of these aldehydes was demonstrated in the synthesis of pine beetle pheromones (+)-exo-brevicomin, (+)-iso-exo-brevicomin and a formal synthesis of 2,7cis-disubstituted oxepane (-)-isolaurepan. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.05.014

文献信息

• Enantioselective synthesis of α-benzyloxy-ω-alkenals: application to the synthesis of (+)-exo-brevicomin, (+)-iso-exo-brevicomin, and (−)-isolaurepan
  作者：Kavirayani R. Prasad、Pazhamalai Anbarasan

  DOI：10.1016/j.tetasy.2007.05.014

  日期：2007.7

  The enantioselective synthesis of alpha-benzyloxy aldehydes containing a terminal alkene was carried out from chiral Pool L-(+)tartaric acid by employing the stereoselective reduction of a 1,4-diketone as the key step. The synthetic utility of these aldehydes was demonstrated in the synthesis of pine beetle pheromones (+)-exo-brevicomin, (+)-iso-exo-brevicomin and a formal synthesis of 2,7cis-disubstituted oxepane (-)-isolaurepan. (c) 2007 Elsevier Ltd. All rights reserved.