Trimethyl-[((8Z,11Z)-tetradeca-8,11-dienyl)oxy]-silane | 177408-55-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: Trimethyl-[((8Z,11Z)-tetradeca-8,11-dienyl)oxy]-silane
• 英文别名: (8Z,11Z)-trimethylsiloxy-8,11-tetradecadiene；trimethyl-[(8Z,11Z)-tetradeca-8,11-dienoxy]silane
• CAS: 177408-55-8
• 化学式: C₁₇H₃₄OSi
• 分子量: 282.542
• InChiKey: SATUSZVXVKDSBW-HZJYTTRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.09
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Trimethyl-[((8Z,11Z)-tetradeca-8,11-dienyl)oxy]-silane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (8Z,11Z)-Tetradeca-8,11-dien-1-ol
  参考文献：
  名称：

  Sex pheromone of tomato pestScrobipalpuloides absoluta (Lepidoptera: Gelechiidae)

  摘要：

  The sex attractant of Scrobipalpuloides absoluta females is a 90:10 mixture of (3E,8Z,11Z)-3,8,11-tetradecatrien-1-yl acetate and (3E,8Z)-3,8-tetradecadien-1-yl acetate. Tetradecadienyl acetates bearing 8Z,11Z; 3E,8Z; and 3E,11Z double bonds were synthesized by stereospecific procedures; the mass spectral and gas chromatographic properties of the 3E,8Z isomer were found to be congruent with those of the tetradecadienyl acetate from S. absoluta. In wind tunnel bioassays, a 10:1 mixture of synthetic (3E,8Z,11Z)3,8,11-tetradecatrien-1-yl acetate and (3E,8Z)-3,8-tetradecadien-1-yl acetate was highly attractive to S. absoluta males. Interestingly, the presence of (8Z, 11Z)-8,11-tetradecadien-1-yl acetate (10%) inhibited the response to (3E,8Z,11Z)-3,8,11-tetradecatrien-1-yl acetate completely.

  DOI：

  10.1007/bf02033586
• 作为产物：
  描述：

  4-碘丁氧基(三甲基)硅烷 、 (4Z,7Z)-1-bromo-4,7-decadiene 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 Trimethyl-[((8Z,11Z)-tetradeca-8,11-dienyl)oxy]-silane
  参考文献：
  名称：

  Sex pheromone of tomato pestScrobipalpuloides absoluta (Lepidoptera: Gelechiidae)

  摘要：

  The sex attractant of Scrobipalpuloides absoluta females is a 90:10 mixture of (3E,8Z,11Z)-3,8,11-tetradecatrien-1-yl acetate and (3E,8Z)-3,8-tetradecadien-1-yl acetate. Tetradecadienyl acetates bearing 8Z,11Z; 3E,8Z; and 3E,11Z double bonds were synthesized by stereospecific procedures; the mass spectral and gas chromatographic properties of the 3E,8Z isomer were found to be congruent with those of the tetradecadienyl acetate from S. absoluta. In wind tunnel bioassays, a 10:1 mixture of synthetic (3E,8Z,11Z)3,8,11-tetradecatrien-1-yl acetate and (3E,8Z)-3,8-tetradecadien-1-yl acetate was highly attractive to S. absoluta males. Interestingly, the presence of (8Z, 11Z)-8,11-tetradecadien-1-yl acetate (10%) inhibited the response to (3E,8Z,11Z)-3,8,11-tetradecatrien-1-yl acetate completely.

  DOI：

  10.1007/bf02033586

文献信息

• Tetradecatrienyl and tetradecadienyl acetates and their use as sex
  申请人：Cornell Research Foundation, Inc.

  公开号：US05728376A1

  公开（公告）日：1998-03-17

  The present invention is directed to compounds useful as moth attractants and to methods for controlling populations of the tomato moth Scrobipalpuloides absoluta with these compounds. The compounds are 3,8,11-tetradecatrienyl acetates, 3,8-tetradecadienyl acetates, 3,11-tetradecadienyl acetates, and 8,11-tetradecadienyl acetates. Preferred compounds are (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate, (3E,8Z)-3,8-tetradecadienyl acetate, (3E,11Z)-3,11 -tetradecadienyl acetate, and (8Z,11Z)-8-11-tetradecadienyl acetate. The compounds can be used as an attractant in moth traps comprising, in addition to the compounds, a moth restraint. Alternatively, the compounds of the present invention can be combined with a biocontrol agent or an insecticide for use as a moth control composition. Synthesis of (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate is described.

  本发明涉及用于吸引飞蛾的化合物以及使用这些化合物控制番茄飞蛾Scrobipalpuloides absoluta种群的方法。这些化合物是3,8,11-四十四碳烯酸乙酯，3,8-四十四碳二烯酸乙酯，3,11-四十四碳二烯酸乙酯和8,11-四十四碳二烯酸乙酯。首选化合物是(3E,8Z,11Z)-3,8,11-四十四碳烯酸乙酯，(3E,8Z)-3,8-四十四碳二烯酸乙酯，(3E,11Z)-3,11-四十四碳二烯酸乙酯和(8Z,11Z)-8-11-四十四碳二烯酸乙酯。这些化合物可以用作飞蛾诱捕器中的诱引剂，除了化合物外，还包括飞蛾约束器。或者，本发明的化合物可以与生物控制剂或杀虫剂结合使用，用作飞蛾控制组合物。描述了(3E,8Z,11Z)-3,8,11-四十四碳烯酸乙酯的合成方法。
• Sex pheromone of tomato pestScrobipalpuloides absoluta (Lepidoptera: Gelechiidae)
  作者：Aleš Svatoš、Athula B. Attygalle、Gulab N. Jham、Rosa T. S. Frighetto、Evaldo F. Vilela、David Šaman、Jerrold Meinwald

  DOI：10.1007/bf02033586

  日期：1996.4

  The sex attractant of Scrobipalpuloides absoluta females is a 90:10 mixture of (3E,8Z,11Z)-3,8,11-tetradecatrien-1-yl acetate and (3E,8Z)-3,8-tetradecadien-1-yl acetate. Tetradecadienyl acetates bearing 8Z,11Z; 3E,8Z; and 3E,11Z double bonds were synthesized by stereospecific procedures; the mass spectral and gas chromatographic properties of the 3E,8Z isomer were found to be congruent with those of the tetradecadienyl acetate from S. absoluta. In wind tunnel bioassays, a 10:1 mixture of synthetic (3E,8Z,11Z)3,8,11-tetradecatrien-1-yl acetate and (3E,8Z)-3,8-tetradecadien-1-yl acetate was highly attractive to S. absoluta males. Interestingly, the presence of (8Z, 11Z)-8,11-tetradecadien-1-yl acetate (10%) inhibited the response to (3E,8Z,11Z)-3,8,11-tetradecatrien-1-yl acetate completely.