| 1240505-09-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• CAS: 1240505-09-2
• 化学式: C₁₅H₂₄O₅
• 分子量: 284.353
• InChiKey: QVSGSUJNVCSEGA-JEMZPZRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  20.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以81%的产率得到methyl (E)-3-[(1R)-1-(3-hydroxypropyl)-2-propenyl]oxy-2-propenoate
  参考文献：
  名称：

  Stereoselective formal synthesis of aspergillide A

  摘要：

  The stereoselective formal synthesis of aspergillide A (1), a cytotoxic 14-membered macrolide, is disclosed. The key intermediate, a trisubstituted tetrahydropyran core is prepared by SmI(2)-induced intramolecular reductive cyclization as well as by using sequential alpha-aminooxylation, Homer-Wadsworth-Emmons olefination, and followed by Oxa-Michael cyclization. Other notable transformations in the synthesis include the use of Jacobsen's hydrolytic kinetic resolution, esterification, ring-closing metathesis (RCM), and cross-metathesis (CM) reactions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.06.013
• 作为产物：
  描述：

  (3R)-6-(tetrahydro-2H-2-pyranyloxy)-1-hexen-3-ol 、 丙炔酸甲酯 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以90%的产率得到
  参考文献：
  名称：

  Stereoselective formal synthesis of aspergillide A

  摘要：

  The stereoselective formal synthesis of aspergillide A (1), a cytotoxic 14-membered macrolide, is disclosed. The key intermediate, a trisubstituted tetrahydropyran core is prepared by SmI(2)-induced intramolecular reductive cyclization as well as by using sequential alpha-aminooxylation, Homer-Wadsworth-Emmons olefination, and followed by Oxa-Michael cyclization. Other notable transformations in the synthesis include the use of Jacobsen's hydrolytic kinetic resolution, esterification, ring-closing metathesis (RCM), and cross-metathesis (CM) reactions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.06.013