methyl (3S,4E,6E,11R)-3,11-dihydroxydodeca-4,6-dienoate | 1312756-63-0

• 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: methyl (3S,4E,6E,11R)-3,11-dihydroxydodeca-4,6-dienoate
• CAS: 1312756-63-0
• 化学式: C₁₃H₂₂O₄
• 分子量: 242.315
• InChiKey: GVJKTSZFVVRYJO-CYBGITEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (3S,4E,6E,11R)-3,11-dihydroxydodeca-4,6-dienoate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以93%的产率得到(3S,4E,6E,11R)-3,11-dihydroxydodeca-4,6-dienoic acid
  参考文献：
  名称：

  Stereoselective total synthesis of ieodomycin C

  摘要：

  A concise stereoselective synthesis of the marine natural product ieodomycin C (3) has been achieved from commercially available pyridinium-1-sulfonate (8) in eight linear steps and 14% overall yield. The key synthetic steps included a B-alkyl Suzuki-Miyaura cross-coupling reaction and an Evans-Nagao acetate aldol reaction. The same synthetic sequence was used for preparing the enantiomer of ieodomycin C (3). Our efforts confirmed the structure of the antibacterial natural product 3. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.020
• 作为产物：
  描述：

  (R)-4-<(tert-butyldimethylsilyl)oxy>-1-pentene 在 potassium phosphate 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 methyl (3S,4E,6E,11R)-3,11-dihydroxydodeca-4,6-dienoate
  参考文献：
  名称：

  Stereoselective total synthesis of ieodomycin C

  摘要：

  A concise stereoselective synthesis of the marine natural product ieodomycin C (3) has been achieved from commercially available pyridinium-1-sulfonate (8) in eight linear steps and 14% overall yield. The key synthetic steps included a B-alkyl Suzuki-Miyaura cross-coupling reaction and an Evans-Nagao acetate aldol reaction. The same synthetic sequence was used for preparing the enantiomer of ieodomycin C (3). Our efforts confirmed the structure of the antibacterial natural product 3. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.020

文献信息

• Ieodomycins A–D, Antimicrobial Fatty Acids from a Marine <i>Bacillus</i> sp.
  作者：M. A. Mojid Mondol、Ji Hye Kim、Min ah Lee、Fakir Shahidullah Tareq、Hyi-Seung Lee、Yeon-Ju Lee、Hee Jae Shin

  DOI：10.1021/np200223r

  日期：2011.7.22

  Bioassay-guided isolation of the EtOAc extract of a marine Bacillus sp., cultured in modified Bennett's broth medium, yielded four new antimicrobial fatty acids, named ieodomycins A-D (1-4). The planar structures of these new compounds were determined by extensive 1D and 2D NMR and HRESIMS spectroscopic data analysis. Their absolute configurations were elucidated by modified Mosher's method and literature data review. All four new compounds (1-4) demonstrated antimicrobial activities in vitro.
• Stereoselective total synthesis of ieodomycin C
  作者：Jørn E. Tungen、Marius Aursnes、Trond Vidar Hansen

  DOI：10.1016/j.tet.2014.04.020

  日期：2014.6

  A concise stereoselective synthesis of the marine natural product ieodomycin C (3) has been achieved from commercially available pyridinium-1-sulfonate (8) in eight linear steps and 14% overall yield. The key synthetic steps included a B-alkyl Suzuki-Miyaura cross-coupling reaction and an Evans-Nagao acetate aldol reaction. The same synthetic sequence was used for preparing the enantiomer of ieodomycin C (3). Our efforts confirmed the structure of the antibacterial natural product 3. (C) 2014 Elsevier Ltd. All rights reserved.