germacra-4(15),5,10(14)-trien-1-one | 84002-60-8

• 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: germacra-4(15),5,10(14)-trien-1-one
• 英文别名: (5E,7S)-4,10-dimethylidene-7-propan-2-ylcyclodec-5-en-1-one
• CAS: 84002-60-8
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: DCXWDHRJJUEDIX-GPAKFWEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  germacra-4(15),5,10(14)-trien-1-one 生成 (5E,7S,10R)-10-methyl-4-methylidene-7-propan-2-ylcyclodec-5-en-1-one
  参考文献：
  名称：

  NISINO, TIKAO;MANABEH, SYUNITI

  摘要：

  DOI：
• 作为产物：
  描述：

  (-)-菊酯D 在 叔丁基过氧化氢 、 selenium(IV) oxide 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 乙醚 、 二氯甲烷 、 环己烷 、 水 为溶剂， 反应 35.0h， 生成 germacra-4(15),5,10(14)-trien-1-one
  参考文献：
  名称：

  Enantiomeric Resolution of a Germacrene-D Derivative by Chiral High-performance Liquid Chromatography

  摘要：

  采用高效液相色谱法和手性固定相对胚芽烯-D 衍生物 (5E,7S*,9S*)-9-羟基-7-异丙基-4,10-双(甲基烯)-5-环癸烯-1-酮进行了直接对映体解析。该方法表明，依兰油中所含的胚芽烯-D 的等效度为 98%，而从 Solidago altissima L. 中提取的胚芽烯-D 几乎是外消旋的。

  DOI：

  10.1271/bbb.61.547

文献信息

• Total synthesis of (−)-periplanones C and D. Their pheromonal activities against three Periplaneta species
  作者：Yoshinori Nishii、Keisuke Watanabe、Taichi Yoshida、Tatsutoshi Okayama、Shozo Takahashi、Yoo Tanabe

  DOI：10.1016/s0040-4020(97)00424-9

  日期：1997.5

  Total synthesis of(-)-periplanones C [(-)-PC; 1] and D [(-)-PD; 2] was achieved starting from (-)-germacrene D via 7 and 8 steps, respectively, according to the similar route on syntheses of racemic PC and PD. The H-1 NMR and GC mass spectra of 2 unambiguously determined the structure of the natural sample of PD which was isolated from Periplaneta fuliginosa. Bioassay of synthetic samples of 1 and 2 was carried out against males of P. fuliginosa, P. americana, and P. japonica. 10(-9) g of 1 elicited significant response in males of P. americana and P. japonica. 10(-10) g of 2 elicited strong response in P. fuliginosa males, whereas it showed significantly weak response against males of P. americana and P. japonica. Almost same degree of activities was observed between 1 and 2 against males of P. americana and P. japonica at 10(-10) g dose. (C) 1997 Published by Elsevier Science Ltd.
• SHIZURI, YOSHIKAZU;YAMAGUCHI, SHU;YAMAMURA, SHOSUKE ISHIHARA MAKOTO;OHBA,+, TETRAHEDRON LETT., 28,(1987) N 33, 3831-3834
  作者：SHIZURI, YOSHIKAZU、YAMAGUCHI, SHU、YAMAMURA, SHOSUKE ISHIHARA MAKOTO、OHBA,+

  DOI：——

  日期：——