Motualevic Acid D | 1108739-49-6

• 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 D
• 英文别名: (2E)-14,14-dibromo-N-[2-(dimethylamino)-2-oxoethyl]tetradeca-2,13-dienamide
• CAS: 1108739-49-6
• 化学式: C₁₈H₃₀Br₂N₂O₂
• 分子量: 466.256
• InChiKey: HHSYNRAEKYRCPT-WYMLVPIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 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 93.83h， 生成 Motualevic Acid D
  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

• 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.