ethyl (5R,2Z)-5-tetrahydropyranyloxyhepta-2,6-dienoate | 1398309-17-5

• 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: ethyl (5R,2Z)-5-tetrahydropyranyloxyhepta-2,6-dienoate
• 英文别名: ethyl (2Z,5R)-5-(oxan-2-yloxy)hepta-2,6-dienoate
• CAS: 1398309-17-5
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: MZQBSOCPAPTUPR-QRKUJVCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  ethyl (5R,2Z)-5-tetrahydropyranyloxyhepta-2,6-dienoate 在 4-甲基苯磺酸吡啶 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以84%的产率得到(R)-6-vinyl-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  A chemoenzymatic asymmetric synthesis of (+)-strictifolione

  摘要：

  A chemoenzymatic asymmetric synthesis of the title compound has been developed using an efficient lipase-catalyzed acylation and a chiral reagent-directed diastereoselective allylation as the key steps for incorporating the stereogenic centers. A cross metathesis was employed to obtain the required E-olefin geometry of the target compound. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.06.015
• 作为产物：
  描述：

  5-((tert-butyldimethylsilyl)oxy)pent-1-en-3-ol 在 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 sodium acetate 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 三苯基膦 、 pyridinium chlorochromate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 87.25h， 生成 ethyl (5R,2Z)-5-tetrahydropyranyloxyhepta-2,6-dienoate
  参考文献：
  名称：

  A chemoenzymatic asymmetric synthesis of (+)-strictifolione

  摘要：

  A chemoenzymatic asymmetric synthesis of the title compound has been developed using an efficient lipase-catalyzed acylation and a chiral reagent-directed diastereoselective allylation as the key steps for incorporating the stereogenic centers. A cross metathesis was employed to obtain the required E-olefin geometry of the target compound. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.06.015

文献信息

• A chemoenzymatic asymmetric synthesis of (+)-strictifolione
  作者：Sneha Ghadigaonkar、Mrunesh R. Koli、Sunita S. Gamre、Manoj K. Choudhary、Subrata Chattopadhyay、Anubha Sharma

  DOI：10.1016/j.tetasy.2012.06.015

  日期：2012.7

  A chemoenzymatic asymmetric synthesis of the title compound has been developed using an efficient lipase-catalyzed acylation and a chiral reagent-directed diastereoselective allylation as the key steps for incorporating the stereogenic centers. A cross metathesis was employed to obtain the required E-olefin geometry of the target compound. (C) 2012 Elsevier Ltd. All rights reserved.