cyclolobatriene | 1359015-47-6

• 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: cyclolobatriene
• 英文别名: 2-[(2R)-5-[(1S,3E,7E)-4,8-dimethylcyclodeca-3,7-dien-1-yl]-3,6-dihydro-2H-pyran-2-yl]propan-2-ol
• CAS: 1359015-47-6
• 化学式: C₂₀H₃₂O₂
• 分子量: 304.473
• InChiKey: QYYYSRKHZDULBG-ZGEIHLPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cyclolobatriene 以 氘代二甲亚砜 为溶剂， 反应 13.0h， 以1.8 mg的产率得到lobatriene
  参考文献：
  名称：

  Cyclolobatriene, a novel prenylated germacrene diterpene, from the soft coral Lobophytum pauciflorum

  摘要：

  A new 10-membered-ring diterpene, cyclolobatriene (1), along with three other known diterpenes, lobatriene (2), eunicol (3), and fuscol (4), were isolated from the Okinawan soft coral Lobophytum pauciflorum. Their structures were established by extensive NMR spectroscopic analyses. Cyclolobatriene (1) is an additional example of rare prenylated germacrenes. Although 1, due to a 10-membered-ring structure, exists as an equilibrium mixture of three conformers, the NMR measurement in CDCl(3) at 7 degrees C enabled us to assign the NMR signals of the three, which is the first example of the complete NMR assignment of all the existing conformers of germacrene-type compounds. Cyclolobatriene (1) was thermally unstable and converted into 2 through Cope rearrangement upon heating at 70 degrees C. Eunicol (3) also possesses the same prenylated germacrene structure as 1, showing similar physico-chemical properties to 1. All four compounds 1-4 showed cytotoxic effect with IC(50)'s of 0.64, 0.41, 0.35 and 0.52 mu M, respectively, against human epidermoid carcinoma A431 cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.012

文献信息

• Cyclolobatriene, a novel prenylated germacrene diterpene, from the soft coral Lobophytum pauciflorum
  作者：Sudhakar V.S. Govindam、Yukio Yoshioka、Akihiko Kanamoto、Takeshi Fujiwara、Tetsuji Okamoto、Makoto Ojika

  DOI：10.1016/j.bmc.2011.12.012

  日期：2012.1

  A new 10-membered-ring diterpene, cyclolobatriene (1), along with three other known diterpenes, lobatriene (2), eunicol (3), and fuscol (4), were isolated from the Okinawan soft coral Lobophytum pauciflorum. Their structures were established by extensive NMR spectroscopic analyses. Cyclolobatriene (1) is an additional example of rare prenylated germacrenes. Although 1, due to a 10-membered-ring structure, exists as an equilibrium mixture of three conformers, the NMR measurement in CDCl(3) at 7 degrees C enabled us to assign the NMR signals of the three, which is the first example of the complete NMR assignment of all the existing conformers of germacrene-type compounds. Cyclolobatriene (1) was thermally unstable and converted into 2 through Cope rearrangement upon heating at 70 degrees C. Eunicol (3) also possesses the same prenylated germacrene structure as 1, showing similar physico-chemical properties to 1. All four compounds 1-4 showed cytotoxic effect with IC(50)'s of 0.64, 0.41, 0.35 and 0.52 mu M, respectively, against human epidermoid carcinoma A431 cells. (C) 2011 Elsevier Ltd. All rights reserved.