1β-hydroxy-4(15),5E,10(14)-germacratriene | 81968-62-9

• 物质功能分类: 天然产物 - 倍半萜
• 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: 1β-hydroxy-4(15),5E,10(14)-germacratriene
• 英文别名: (1R,7S,E)-7-isopropyl-4,10-dimethylenecyclodec-5-enol；5-cyclodecen-1-ol, 4,10-bis(methylene)-7-(1-methylethyl)-, (1R,5E,7S)-；(1R,5E,7S)-4,10-dimethylidene-7-propan-2-ylcyclodec-5-en-1-ol
• CAS: 81968-62-9
• 化学式: C₁₅H₂₄O
• 分子量: 220.355
• InChiKey: OSSWBZXPRYZGRO-YKHJJTLOSA-N

物化性质

• 沸点：
  321.1±42.0 °C(Predicted)
• 密度：
  0.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2906199090

反应信息

• 作为反应物：
  描述：

  1β-hydroxy-4(15),5E,10(14)-germacratriene 在 吡啶 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 manganese(IV) oxide 、 正丁基锂 、 selenium(IV) oxide 、 四甲基乙二胺 作用下， 以 正己烷 、 苯 为溶剂， 反应 13.0h， 生成 (3Z,7E,9S)-9-isopropyl-2,6-bis(methylene)-3,7-cyclodecadien-1-one
  参考文献：
  名称：

  Total synthesis of (−)-periplanones C and D. Their pheromonal activities against three Periplaneta species

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(97)00424-9
• 作为产物：
  描述：

  (-)-菊酯D 在 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 乙醚 、 环己烷 为溶剂， 反应 11.0h， 生成 1β-hydroxy-4(15),5E,10(14)-germacratriene
  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

• Enantiomeric Resolution of a Germacrene-D Derivative by Chiral High-performance Liquid Chromatography
  作者：Yoshinori Nishii、Taichi Yoshida、Yoo Tanabe

  DOI：10.1271/bbb.61.547

  日期：1997.1

  Direct enantiomeric resolution of the germacrene-D derivative, (5E,7S*,9S*)-9-hydroxy-7-isopropyl-4,10-bis(methyIene)-5-cyclodecen-1-one, was carried out by HPLC with a chiral stationary phase. This method showed that germacrene-D contained in ylang ylang oil was 98% e.e., whereas germacrene-D extracted from Solidago altissima L. was almost racemic.

  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。
• Eremophilene and germacrene derivatives from Senecio glanduloso-pilosus
  作者：Ferdinand Bohlmann、Rajinder K. Gupta

  DOI：10.1016/0031-9422(82)85266-7

  日期：1982.1

  Abstract Senecio glanduloso-pilosus afforded in addition to known compounds a new eremophilene deriva- tive and a hydroperoxide derived from germacrene D.

  摘要除了已知化合物外，千叶千里光还提供了一种新的 eremophilene 衍生物和一种衍生自锗烯 D 的氢过氧化物。
• Itokawa, Hideji; Matsumoto, Hajime; Mihashi, Susumu, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 5, p. 1743 - 1745
  作者：Itokawa, Hideji、Matsumoto, Hajime、Mihashi, Susumu

  DOI：——

  日期：——
• 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：——
• 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.

表征谱图