(3S,4E,6E,11R)-3,11-dihydroxydodeca-4,6-dienoic acid | 1312925-57-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (3S,4E,6E,11R)-3,11-dihydroxydodeca-4,6-dienoic acid
• 英文别名: ieodomycin C；leodomycin D
• CAS: 1312925-57-7
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: LWHVEMXRYKVHKX-HKSGNEMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4E,6E,11R)-3,11-dihydroxydodeca-4,6-dienoic acid 在 吡啶 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (2R,6E,8E,10S)-12-methoxy-12-oxododeca-6,8-diene-2,10-diyl (2R,2'R)-bis(3,3,3-trifluoro-2-methoxy-2-phenylpropanoate)
  参考文献：
  名称：

  Ieodomycins A–D, Antimicrobial Fatty Acids from a Marine Bacillus sp.

  摘要：

  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.

  DOI：

  10.1021/np200223r
• 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 、 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 (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

文献信息

• Stereoselective Concise Total Synthesis of Leodomycin C and D
  作者：Y. Venkateswarlu、B. Chinnababu、S. Reddy、D. Reddy、D. Rao

  DOI：10.1055/s-0031-1289640

  日期：2012.1

  Stereoselective concise total synthesis of leodomycin C and D from commercially available propylene oxide using Jacobsen’s hydrolytic kinetic resolution (HKR), base-promoted alkyne zipper reaction, TPP-promoted enyne ester (ynoate) to diene ester (dienoate) isomerization, and (R)-(+)-2-methyl-CBS-oxazaborolidine reduction as key steps is reported. Bacillus sp - leodomycin C and D - antimicrobial activity

  使用雅各布森的水解动力学拆分（HKR），碱促进的炔烃拉链反应，TPP促进的炔烃酯（壬酸酯）到二烯酯（二烯酸酯）异构化和（R），从市售的环氧丙烷中立体选择性地简明地合成Leodomycin C和D据报道，-（+）-2-甲基-CBS-恶唑硼烷还原是关键步骤。 芽孢杆菌-Leodomycin C和D-抗菌活性-水解动力学拆分-HKR-炔拉链反应-（R）-（+）-2-甲基-CBS-恶唑硼烷
• 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.
• 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.