3-dodecen-11-olide | 87583-37-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: 3-dodecen-11-olide
• 英文别名: (Z)-12-methyloxacyclododec-4-en-2-one；(z)-3-Dodecen-11-olide；(4Z)-12-methyl-1-oxacyclododec-4-en-2-one
• CAS: 87583-37-7
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: IIBFPGGSICFOHJ-VURMDHGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  10-烯酸甲酯 在 吡啶 、 titanium(IV) isopropylate 、 lithium hydroxide 、 chloroborane methyl sulfide complex 、 苯基溴化硒 、 水 、 双氧水 、 四氯化钛 、 三苯基膦 、 pyridinium chlorochromate 、 lithium diisopropyl amide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 水 、 甲苯 为溶剂， 反应 19.0h， 生成 3-dodecen-11-olide
  参考文献：
  名称：

  The Synthesis of (±)-Patulolide C and its Epimer Via Dodec-3-En-11-Olide

  摘要：

  A novel route to dodec-3-en-11-olide 3, a macrolide pheromone of cucujid grain beetles is reported. Compound 3 provides an access to the antimicrobial (+/-)-patulolides and (+/-)-epipatulolide C. Conformational restrictions hamper the rearrangement of the 12-membered beta gamma-epoxylactones 7 to corresponding allylic alcohols 2.

  DOI：

  10.1080/00397919908085781

文献信息

• A versatile and convenient protocol for the stereocontrolled synthesis of olefinic insect pheromones
  作者：Andrei A. Vasil'ev、Alexei L. Vlasyuk、Galina D. Gamalevich、Edward P. Serebryakov

  DOI：10.1016/0968-0896(96)00016-8

  日期：1996.3

  supplemented by an enzymatic hydrolysis, was successfully applied to the synthesis of configurationally pure (gp > or = 98%) pheromones of the furniture carpet beetle, dry bean beetle, rusty grain beetle, square-necked grain beetle and a trail-following pheromone mimic for subterranean termites.

  2,4-二烯酸烷基酯的Horner-Emmons合成与在复杂的L.Cr（CO）3催化剂（L = 3CO或芳烃）上的氢化反应相结合，提供了一种通用的，立体控制的且操作简单的方法（Z）-二取代的（Z）-三取代的（E）-三取代的烯烃和跳过的（Z，Z）-二取代的二烯烃具有均聚物类型的功能。该方案，有时还辅以酶促水解，已成功地应用于家具地毯甲虫，干豆甲虫，生锈的谷物甲虫，方颈谷物甲虫和小径的构型纯（gp>或= 98％）信息素的合成信息素模仿地下白蚁。
• Beetle attractant
  申请人：——

  公开号：US04560551A1

  公开（公告）日：1985-12-24

  An insect trap is provided which contains an attractant comprising a sufficient amount of unsaturated oxacyclododecanone selected from the group consisting of (Z-12-methyloxacyclododec-4-en-2-one (I),(Z,Z)-12-methyloxacyclododeca-4,7-dien-2-one (II), and the alkyl substituted products of the foregoing, the amount of the attractant being sufficient so as to effectively attract O. mercator beetles. The attractant may also comprise an aldehyde, preferably hexanal, octanal, or nonanal, and preferably in combination with I or II, or both.

  提供了一种昆虫诱捕器，其中包含一种吸引剂，该吸引剂包含足够量的未饱和氧杂环十二酮，所述氧杂环十二酮选自以下组合之一：(Z-12-甲氧氧杂环十二烯-4-烯-2-酮(I))，(Z,Z)-12-甲氧氧杂环十二烯-4,7-二烯-2-酮(II)，以及前述化合物的烷基取代产物，所述吸引剂的量足以有效吸引O. mercator 甲虫。该吸引剂也可以包含醛类物质，最好是己醛、辛醛或壬醛，最好与I或II，或两者结合使用。
• A Concise, Efficient and Flexible Strategy for the Synthesis of the Pheromones of<i>Oryzaephilus</i>and<i>Cryptolestes</i>Grain Beetles
  作者：Christopher D. J. Boden、John Chambers、Ian D. R. Stevens

  DOI：10.1055/s-1993-25874

  日期：——

  Six of the seven macrolide components of the pheromone systems of grain beetles of the genera Oryzaephilus and Cryptolestes are synthesised by new routes of greatly improved efficiency. Iterative methodology based on the Wittig olefination is employed for the construction of the (Z,Z)-1,4-diene subunits in three of the lactones; chlorite oxidation of (Z)-3-alkenals derived by this methodology is used to form the (Z)-3-alkenoic acid functionalities present in four of the targets. The use of recently described conditions for the cyclisation of a Combretastatin analogue gives dramatically increased yields for the macrolactonisation steps in all six cases.

  稻属和隐甲虫属的谷甲虫信息素系统的七种大环内酯成分中的六种是通过新路线合成的，效率大大提高。采用基于 Wittig 烯化的迭代方法在三个内酯中构建 (Z,Z)-1,4-二烯亚单元；通过该方法衍生的 (Z)-3-烯醛的亚氯酸盐氧化用于形成四个靶标中存在的 (Z)-3-烯酸官能团。在所有六种情况下，使用最近描述的康布他汀类似物环化条件可显着提高大内酯化步骤的产率。
• Polyamide-polyether block copolymer
  申请人：Pavlin S. Mark

  公开号：US20060052576A1

  公开（公告）日：2006-03-09

  Copolymers having linked internal polyether blocks and internal polyamide blocks have advantageous physical properties and solvent-gelling abilities. The copolymer may be prepared from a reaction mixture that contains 1,4-cyclohexane dicarboxylic acid (CHDA) and poly(alkyleneoxy) diamine (PAODA). Optionally, the reaction mixture contains no monofunctional compound reactive with either amine or carboxylic acid groups, however some of this monofunctional compound may be present. Dimer diamine and/or dimer acid may be present in the reaction mixture. A copolymer may also be prepared from a reaction mixture containing dimer acid and at least two diamine compound(s) including PAODA and short-chain aliphatic diamine having 2-6 carbons (SDA), wherein: a) the reaction mixture comprises x grams of PAODA and y grams of SDA, and x/(x+y) is 0.8-0.98; b) the reaction mixture weighs z grams, and x/z is at least 0.25; and c) the reaction mixture contains either no co-diacid, or comprises a small amount of co-diacid, wherein, if the reaction mixture comprises a small amount of co-diacid, then acid equivalents from co-diacid contribute less than 25% of the total acid equivalents present in the reaction mixture.

  具有连接的内部聚醚块和内部聚酰胺块的共聚物具有有利的物理性能和溶剂凝胶能力。该共聚物可以从包含1,4-环己烷二甲酸（CHDA）和聚（烷氧基）二胺（PAODA）的反应混合物中制备。可选地，反应混合物不含与胺或羧酸基反应的单官能化合物，但其中一些单官能化合物可能存在。二聚胺和/或二聚酸可以存在于反应混合物中。还可以从包含二聚酸和至少两种二胺化合物（包括PAODA和具有2-6个碳的短链脂肪族二胺（SDA））的反应混合物中制备共聚物，其中：a）反应混合物包含x克PAODA和y克SDA，且x/（x+y）为0.8-0.98；b）反应混合物重z克，且x/z至少为0.25；c）反应混合物不含共二酸，或包含少量共二酸，其中，如果反应混合物包含少量共二酸，则共二酸的酸当量贡献的总酸当量不超过反应混合物中总酸当量的25％。
• POLYAMIDE-POLYETHER BLOCK COPOLYMER
  申请人：Pavlin S. Mark

  公开号：US20070244294A1

  公开（公告）日：2007-10-18

  Copolymers having linked internal polyether blocks and internal polyamide blocks have advantageous physical properties and solvent-gelling abilities. The copolymer may be prepared from a reaction mixture that contains 1,4-cyclohexane dicarboxylic acid (CHDA) and poly(alkyleneoxy) diamine (PAODA). Optionally, the reaction mixture contains no monofunctional compound reactive with either amine or carboxylic acid groups, however some of this monofunctional compound may be present. Dimer diamine and/or dimer acid may be present in the reaction mixture. A copolymer may also be prepared from a reaction mixture containing dimer acid and at least two diamine compound(s) including PAODA and short-chain aliphatic diamine having 2-6 carbons (SDA), wherein: a) the reaction mixture comprises x grams of PAODA and y grams of SDA, and x/(x+y) is 0.8-0.98; b) the reaction mixture weighs z grams, and x/z is at least 0.25; and c) the reaction mixture contains either no co-diacid, or comprises a small amount of co-diacid, wherein, if the reaction mixture comprises a small amount of co-diacid, then acid equivalents from co-diacid contribute less than 25% of the total acid equivalents present in the reaction mixture.

  具有连接的内部聚醚块和内部聚酰胺块的共聚物具有优越的物理性能和溶剂凝胶能力。该共聚物可以从含有1,4-环己烷二羧酸（CHDA）和聚（烷氧基）二胺（PAODA）的反应混合物中制备。可选地，反应混合物不含与胺基或羧酸基反应的单官能化合物，但其中一些单官能化合物可能存在。二聚胺和/或二聚酸可以存在于反应混合物中。共聚物也可以从含有二聚酸和至少两种二胺化合物（包括PAODA和具有2-6个碳的短链脂肪族二胺（SDA））的反应混合物中制备，其中：a）反应混合物包含x克PAODA和y克SDA，且x/（x+y）为0.8-0.98；b）反应混合物重z克，且x/z至少为0.25；c）反应混合物不含共二酸，或包含少量共二酸，其中，如果反应混合物包含少量共二酸，则共二酸的酸当量贡献的总酸当量不超过反应混合物中总酸当量的25％。