Motualevic Acid A | 1108739-39-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Motualevic Acid A
• 英文别名: 2-[[(2E)-14,14-dibromotetradeca-2,13-dienoyl]amino]acetic acid
• CAS: 1108739-39-4
• 化学式: C₁₆H₂₅Br₂NO₃
• 分子量: 439.187
• InChiKey: ZLIHRGDEFDFVOK-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  22
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Motualevic Acid A 在 氯甲酸乙酯 、 三乙胺 、 ammonium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以40%的产率得到Motualevic Acid C
  参考文献：
  名称：

  Total synthesis of motualevic acids A–F, (E) and (Z)-antazirines

  摘要：

  Total synthesis of motualevic acids A-F and (E) & (Z) geometrical isomers of antazirines has been achieved from a commercially available starting material, 1,10-decanediol. The synthesis of motualevic acid E served as a common key intermediate for the synthesis of most of these natural products. The key steps involved in this synthesis were Wittig olefination, Corey-Fuchs reaction, Neber reaction, amide coupling. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.12.092
• 作为产物：
  描述：

  10-溴-1-癸醇 在 草酰氯 、 18-冠醚-6 、 lithium hydroxide monohydrate 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 1-羟基苯并三唑 、 对甲苯磺酸 、 二甲基亚砜 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 90.83h， 生成 Motualevic Acid A
  参考文献：
  名称：

  Total synthesis of motualevic acids A–F, (E) and (Z)-antazirines

  摘要：

  Total synthesis of motualevic acids A-F and (E) & (Z) geometrical isomers of antazirines has been achieved from a commercially available starting material, 1,10-decanediol. The synthesis of motualevic acid E served as a common key intermediate for the synthesis of most of these natural products. The key steps involved in this synthesis were Wittig olefination, Corey-Fuchs reaction, Neber reaction, amide coupling. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.12.092

文献信息

• Motualevic acids and analogs: Synthesis and antimicrobial structure–activity relationships
  作者：Pradeep Cheruku、Jessica L. Keffer、Cajetan Dogo-Isonagie、Carole A. Bewley

  DOI：10.1016/j.bmcl.2010.05.073

  日期：2010.7

  Synthesis of the marine natural products motualevic acids A, E, and analogs in which modifications have been made to the ω-brominated lipid (E)-14,14-dibromotetra-deca-2,13-dienoic acid or amino acid unit are reported, together with antimicrobial activities against Staphylococcus aureus, methicillin-resistant S. aureus, Enterococcus faecium, and vancomycin-resistant Enterococcus.

  海洋天然产物 motualevic 酸 A、E 和类似物的合成，其中已对 ω-溴化脂质 ( E )-14,14-dibromotetra-deca-2,13-dienoic 酸或氨基酸单元进行了修饰，用针对抗微生物活性一起金黄色葡萄球菌，耐甲氧西林金黄色葡萄球菌，屎肠球菌，和耐万古霉素肠球菌。
• Total synthesis of motualevic acids A–E
  作者：Gangarajula Sudhakar、Vilas D. Kadam、Vaddu V.N. Reddy

  DOI：10.1016/j.tetlet.2009.12.113

  日期：2010.2

  The first total synthesis of motualevic acids A-E, isolated from Siliquariaspongia sp., starting from commercially available 1,10-decanediol, is described. The key steps in the synthetic sequence involve stereoselective olefination, Corey-Fuchs reaction, and amide coupling. (C) 2010 Published by Elsevier Ltd.
• Total synthesis of motualevic acids A–F, (E) and (Z)-antazirines
  作者：Vilas D. Kadam、Gangarajula Sudhakar

  DOI：10.1016/j.tet.2014.12.092

  日期：2015.2

  Total synthesis of motualevic acids A-F and (E) & (Z) geometrical isomers of antazirines has been achieved from a commercially available starting material, 1,10-decanediol. The synthesis of motualevic acid E served as a common key intermediate for the synthesis of most of these natural products. The key steps involved in this synthesis were Wittig olefination, Corey-Fuchs reaction, Neber reaction, amide coupling. (C) 2014 Elsevier Ltd. All rights reserved.