3-deoxy-2,3-dehydrolupeol | 75679-46-8

• 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: 3-deoxy-2,3-dehydrolupeol
• 英文别名: lupa-2,20(29)-diene；lupadiene-(2.20(29))；Lupadien-(2.20(29))；Lupa-2,20(29)-dien；(1R,3aR,5aR,5bR,7aS,11aS,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysene
• CAS: 75679-46-8
• 化学式: C₃₀H₄₈
• 分子量: 408.711
• InChiKey: YZNNQGUYLKZCRE-VIUFNMEASA-N

物化性质

• 熔点：
  164-166 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  457.2±25.0 °C(Predicted)
• 密度：
  0.944±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  羽扇豆醇 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 47.0h， 生成 3-deoxy-2,3-dehydrolupeol
  参考文献：
  名称：

  摘要：

  Two methods of obtaining 3alpha-betulinic acid and related compounds from their 3beta-epimers were studied: the reaction of bimolecular substitution and the stereoselective reduction of 3-ketoderivatives. The substitution of acyloxy by formyloxy group in 3-O-tosyllupeol or of the belulin hydroxyl by benzoyloxy group resulted only in Delta(2,3)-elimination products, with none of the expected products of bimolecular substitution being found. The catalytic hydrogenation of betulonic acid over Raney nickel resulted only in reduction of the isopropenyl double bond, whereas the use of 5% Ru/C gave a 60: 40 mixture of epimers of dihydrobetulinic acid. Practically the same mixture of betulinic acid epimers was obtained when reducing betulonic acid with L-Selectride. The cytotoxic activity of 3alpha-betulinic acid increased toward the Bro melanoma cells and decreased toward the MS melanoma cells.

  DOI：

  10.1023/a:1023220701797

文献信息

• An examination of the euphorbiaceae of Hong Kong. Part VIII. Lup-20(29)-ene-3α,23-diol, a new triterpene from Glochidion macrophyllum benth
  作者：W. H. Hui、W. K. Lee

  DOI：10.1039/j39710001004

  日期：——

  The stems of Glochidion macrophyllum Benth. (Euphorbiaceae) have been found to contain a new triterpene, shown to be lup-20(29)-ene-3α,23-diol on the basis of chemical and spectroscopic evidence.

  Glochidion macrophyllum Benth.（大戟科）的茎被发现含有一种新的三萜，根据化学和光谱证据，该物质被确定为狼-20（29）-烯-3α，23-二醇。
• Über Lupeol. (IV. Mitteilung.)
  作者：F. Biedebach

  DOI：10.1002/ardp.19392770404

  日期：——
• 3α-Hydroxy-lup-20(29)-ene-23,28-dioic acid from Schefflera octophylla
  作者：G. Adam、M. Lischewski、H.V. Phiet、A. Preiss、J. Schmidt、T.V. Sung

  DOI：10.1016/0031-9422(82)80147-7

  日期：1982.1