2-{(5E)-2-(Z)-[(4E)-6-(tert-butyldimethylsilyloxy)-4-methylhex-4-enylidene]-6,10-dimethylundeca-5,9-dienyl}isoindole-1,3-dione | 191042-91-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-{(5E)-2-(Z)-[(4E)-6-(tert-butyldimethylsilyloxy)-4-methylhex-4-enylidene]-6,10-dimethylundeca-5,9-dienyl}isoindole-1,3-dione
• CAS: 191042-91-8
• 化学式: C₃₄H₅₁NO₃Si
• 分子量: 549.869
• InChiKey: LMXUIEREYYHSKA-VRIBRMCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.43
• 重原子数：
  39.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-{(5E)-2-(Z)-[(4E)-6-(tert-butyldimethylsilyloxy)-4-methylhex-4-enylidene]-6,10-dimethylundeca-5,9-dienyl}isoindole-1,3-dione 在 正丁胺 作用下， 以 乙醇 为溶剂， 以68%的产率得到(2Z,5E)-2-[(E)-6-[tert-butyl(dimethyl)silyl]oxy-4-methylhex-4-enylidene]-6,10-dimethylundeca-5,9-dien-1-amine
  参考文献：
  名称：

  A highly stereoselective synthesis of plaunotol and its thiourea derivatives as potent antibacterial agents against Helicobacter pylori

  摘要：

  Practical and high ly stereoselective synthesis of diterpene alcohol, plaunotol (1) and its thiourea derivatives 2a, 3a and 4a, via Z-selective Wittig reaction between cc-acetal ketone 5 and phosphonium salt 6 and their antibacterial activity against Helicobacter pylori are described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00203-6
• 作为产物：
  描述：

  (E)-1,1-diethoxy-6,10-dimethyl-undeca-5,9-dien-2-one 在 sodium tetrahydroborate 、 18-冠醚-6 、 potassium hydride 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 2-{(5E)-2-(Z)-[(4E)-6-(tert-butyldimethylsilyloxy)-4-methylhex-4-enylidene]-6,10-dimethylundeca-5,9-dienyl}isoindole-1,3-dione
  参考文献：
  名称：

  A highly stereoselective synthesis of plaunotol and its thiourea derivatives as potent antibacterial agents against Helicobacter pylori

  摘要：

  Practical and high ly stereoselective synthesis of diterpene alcohol, plaunotol (1) and its thiourea derivatives 2a, 3a and 4a, via Z-selective Wittig reaction between cc-acetal ketone 5 and phosphonium salt 6 and their antibacterial activity against Helicobacter pylori are described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00203-6

文献信息

• Synthesis of Plaunotol Derivatives and their Antibacterial Activities against Helicobacter pylori
  作者：Keiko Tago、Emiko Minami、Kayoko Masuda、Toshiyuki Akiyama、Hiroshi Kogen

  DOI：10.1016/s0968-0896(01)00080-3

  日期：2001.7

  Plaunotol, a known antiulcer drug, has antibacterial activities against Helicobacter pylori. Plaunotol thiourea derivatives 2-4 and diol derivatives 6-10 were designed in search For a compound with high amtobacteroa; activities. Thiourea derivatives 2-4 were synthesized regioselectively using our effective synthetic route for plaunotol (1), and diol derivatives 6 10 were also synthesized. Their antibacterial activities against H. pylori are described and we found that the most potent antibacterial agent was Cl-thiourea derivative 2c. (C) 2001 Elsevier Science Ltd. All rights reserved.