(R,E)-methyl 5-hydroxy-8-methyl-3-oxoundeca-8,10-dienoate | 1446794-90-6

• 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: (R,E)-methyl 5-hydroxy-8-methyl-3-oxoundeca-8,10-dienoate
• 英文别名: methyl (5R,8E)-5-hydroxy-8-methyl-3-oxoundeca-8,10-dienoate
• CAS: 1446794-90-6
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: VJVDQOUWAXTKLN-IGLBNKAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R,E)-methyl 5-hydroxy-8-methyl-3-oxoundeca-8,10-dienoate 在 溶剂黄146 、 tetramethylammonium triacetoxyborohydride 、 Rochelle's salt 作用下， 以 乙腈 、 乙酸乙酯 为溶剂， 反应 2.5h， 以90%的产率得到ieodomycin A
  参考文献：
  名称：

  Stereoselective total synthesis of Ieodomycin A and B

  摘要：

  The stereoselective total synthesis of Ieodomycin A and B, bioactive secondary metabolites from marine sources with potent anti-microbial activity was achieved starting from commercially available geranial. The key steps involved in the synthetic sequence of Ieodomycin A and B are the Sharpless asymmetric epoxidation, the formation of a beta-ketoester, and the 1,3-anti reduction. The synthesis of C-3 epimer of Ieodomycin A and B was also accomplished in good yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.05.002
• 作为产物：
  描述：

  (R,E)-methyl 5-(tert-butyldimethylsilyloxy)-8-methyl-3-oxoundeca-8,10-dienoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到(R,E)-methyl 5-hydroxy-8-methyl-3-oxoundeca-8,10-dienoate
  参考文献：
  名称：

  Stereoselective total synthesis of Ieodomycin A and B

  摘要：

  The stereoselective total synthesis of Ieodomycin A and B, bioactive secondary metabolites from marine sources with potent anti-microbial activity was achieved starting from commercially available geranial. The key steps involved in the synthetic sequence of Ieodomycin A and B are the Sharpless asymmetric epoxidation, the formation of a beta-ketoester, and the 1,3-anti reduction. The synthesis of C-3 epimer of Ieodomycin A and B was also accomplished in good yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.05.002

文献信息

• Protection-free, short, and stereoselective synthesis of ieodomycin A and B
  作者：N. Nageswara Rao、H.M. Meshram

  DOI：10.1016/j.tetlet.2013.06.071

  日期：2013.8

  A concise, protection-free, and improved stereoselective total synthesis of ieodomycin A and ieodomycin B is described. The key steps involved in the synthesis are Evans aldol reaction and nucleophilic addition of potassium salt of mono methyl malonate. (C) 2013 Elsevier Ltd. All rights reserved.