(2S,3Z,7E,9S)-9-isopropyl-2-methyl-6-methylene-3,7-cyclodecadien-1-one

• 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: (2S,3Z,7E,9S)-9-isopropyl-2-methyl-6-methylene-3,7-cyclodecadien-1-one
• 英文别名: (2S,3Z,7E,9S)-2-methyl-6-methylidene-9-propan-2-ylcyclodeca-3,7-dien-1-one
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: MXBCSENLKQWEHH-NDJNMMANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 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

• 作为产物：
  描述：

  (-)-菊酯D 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 、 potassium tri-sec-butyl-borohydride 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 13.33h， 生成 (2S,3Z,7E,9S)-9-isopropyl-2-methyl-6-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

文献信息

• Preparation of (−)-Periplanone D and Its Physical and Spectroscopic Properties
  作者：Shigefumi KUWAHARA、Izuru NAGASHIMA、Walter Soares LEAL、Jiro ISHIKAWA、Osamu KODAMA

  DOI：10.1271/bbb.64.600

  日期：2000.1

  (-)-Periplanones C and D were obtained in reproducible yields by modifying reported procedures. Our synthetic sample of (-)-periplanone D showed somewhat different physical and spectroscopic properties from those reported in the literature.

  （-）-Periplanones C和D是通过修改报告的程序以可重复的产量获得的。我们合成的（-）-periplanone D样品的物理和光谱性质与文献报道的有所不同。
• Periplanon D1 und periplanon D2-zwei neue biologisch aktive germacranoide sesquiterpene aus periplaneta americana
  作者：M. Biendl、H. Hauptmann、H. Sass

  DOI：10.1016/s0040-4039(01)80400-7

  日期：——

  Two novel bioactive sesquiterpenes 3 and 4a have been isolated from the faeces of female American cockroaches and identified on the basis of spectroscopic data and comparison with synthetic material.

  从雌性美国蟑螂的粪便中分离出两种新型生物活性倍半萜烯3和4a，并根据光谱数据和与合成材料的比较进行了鉴定。
• BIENDL, M.;HAUPTMANN, H.;SASS, H., TETRAHEDRON LETT., 30,(1989) N8, C. 2367-2368
  作者：BIENDL, M.、HAUPTMANN, H.、SASS, H.

  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.