(6R,7R,8R,9R)-6,9-bis(benzyloxy)tetradeca-1,13-diene-7,8-diol | 874910-12-0

• 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: (6R,7R,8R,9R)-6,9-bis(benzyloxy)tetradeca-1,13-diene-7,8-diol
• 英文别名: (6R,7R,8R,9R)-6,9-bis(phenylmethoxy)tetradeca-1,13-diene-7,8-diol
• CAS: 874910-12-0
• 化学式: C₂₈H₃₈O₄
• 分子量: 438.607
• InChiKey: IFHKBGRGGQIPJX-VIJSPRBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  32
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (6R,7R,8R,9R)-6,9-bis(benzyloxy)tetradeca-1,13-diene-7,8-diol 在 palladium dichloride lead(IV) acetate 、 氧气 、 magnesium bromide 、 copper dichloride 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 8.5h， 生成 (6R,7R)-6-(benzyloxy)-7-hydroxynonan-2-one
  参考文献：
  名称：

  Asymmetric synthesis of unsaturated α-benzyloxyaldehydes: an enantioselective synthesis of (+)-exo-brevicomin

  摘要：

  Enantioselective synthesis of alpha-hydroxy aldehydes with an alkene tether was accomplished front L-(+)-tartaric acid, employing stereoselective reduction of a 1,4-diketone with L-selectride as the key step. Synthetic utility of these aldehydes was demonstrated in the synthesis of pine beetle pheromone (+)-exo-brevicomin. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.035
• 作为产物：
  描述：

  magnesium,pent-1-ene,bromide 在 三氯化铁 、 L-Selectride 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 (6R,7R,8R,9R)-6,9-bis(benzyloxy)tetradeca-1,13-diene-7,8-diol
  参考文献：
  名称：

  Asymmetric synthesis of unsaturated α-benzyloxyaldehydes: an enantioselective synthesis of (+)-exo-brevicomin

  摘要：

  Enantioselective synthesis of alpha-hydroxy aldehydes with an alkene tether was accomplished front L-(+)-tartaric acid, employing stereoselective reduction of a 1,4-diketone with L-selectride as the key step. Synthetic utility of these aldehydes was demonstrated in the synthesis of pine beetle pheromone (+)-exo-brevicomin. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.035

文献信息

• Asymmetric synthesis of unsaturated α-benzyloxyaldehydes: an enantioselective synthesis of (+)-exo-brevicomin
  作者：Kavirayani R. Prasad、Pazhamalai Anbarasan

  DOI：10.1016/j.tetasy.2005.10.035

  日期：2005.12

  Enantioselective synthesis of alpha-hydroxy aldehydes with an alkene tether was accomplished front L-(+)-tartaric acid, employing stereoselective reduction of a 1,4-diketone with L-selectride as the key step. Synthetic utility of these aldehydes was demonstrated in the synthesis of pine beetle pheromone (+)-exo-brevicomin. (c) 2005 Elsevier Ltd. All rights reserved.
• 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.