(2R,3R)-3-(benzyloxy)oct-7-en-2-ol | 950826-37-6

• 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: (2R,3R)-3-(benzyloxy)oct-7-en-2-ol
• 英文别名: (2R,3R)-3-phenylmethoxyoct-7-en-2-ol
• CAS: 950826-37-6
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: MGTXIGGDJDFZIE-UKRRQHHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-(benzyloxy)oct-7-en-2-ol 在 sodium hydride 、 碳酸氢钠 、 臭氧 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (7R,8R)-7,8-bis(benzyloxy)nonan-3-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
• 作为产物：
  描述：

  (4S,5S)-4,5-bis((R)-1-(benzyloxy)hex-5-enyl)-2,2-dimethyl-1,3-dioxolane 在 lead(IV) acetate 、 三氯化铁 、 magnesium bromide 作用下， 以 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 12.0h， 生成 (2R,3R)-3-(benzyloxy)oct-7-en-2-ol
  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.