Methyl 5(E)-decenoate | 84168-29-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Methyl 5(E)-decenoate
• 英文别名: methyl 5-decenoate；Methyl-5-decenoate；methyl (E)-dec-5-enoate
• CAS: 84168-29-6
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: YYRDDAPQDPABPZ-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Methyl 5(E)-decenoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 28.0h， 生成 (E)-5-癸烯-1-乙酸酯
  参考文献：
  名称：

  Vinczer, Peter; Juvancz, Zoltan; Novak, Lajos, Acta Chimica Hungarica, 1988, vol. 125, # 6, p. 797 - 820

  摘要：

  DOI：
• 作为产物：
  描述：

  5-羟基戊酸 在 正丁基锂 、 pyridinium chlorochromate 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 Methyl 5(E)-decenoate
  参考文献：
  名称：

  Vinczer, Peter; Juvancz, Zoltan; Novak, Lajos, Acta Chimica Hungarica, 1988, vol. 125, # 6, p. 797 - 820

  摘要：

  DOI：

文献信息

• Metathesis syntheses of pheromones or their components
  申请人：——

  公开号：US20020022741A1

  公开（公告）日：2002-02-21

  The present invention relates to metathesis syntheses for insect sex-attractant pheromones or their components, such as E-5-decenyl acetate, the major component of the Peach Twig Borer pheromone; (5R, 6S)-6-acetoxy-5-hexadecanolide, the mosquito oviposition attractant pheromone; E9, Z11-hexadecadienal, the pecan nut casebearer moth pheromone; 9-tetradecenyl formate, an analog of the Diamondback Moth (DBM) pheromone; 11-tetradecenyl acetate, the Omnivorous Leafroller (OLR) pheromone; E-4-tridecenyl acetate, the major component of the Tomato Pinworm (TPW) pheromone; E,E-8,10-dodecadienol, the Codling Moth (CM) pheromone. The syntheses preferably employ a Class I-IV metathesis catalyst, entail few reaction steps, use generally commercially available starting materials, and have relatively short process times. These syntheses produce good yields without the need for expensive or sophisticated equipment. The invention also provides an inexpensive route for producing omega-haloalkenols by cross-metathesizing alpha-omega-diacetoxy alkenes and alpha-omega-dihalides to yield omega-haloalkenols, which are easily converted into omega-haloalkanols under traditional hydrogenation methods.

  本发明涉及对昆虫性诱素或其组分进行交换合成，如E-5-癸烯醇醋酸酯，桃枝蠕蛾性信息素的主要成分；（5R, 6S）-6-乙酰氧基-5-十六醇内酯，蚊子产卵引诱素；E9, Z11-癸二烯醛，山核桃果蛾性信息素；9-十四烯酸甲酯，菜青虫性信息素的类似物；11-十四烯醇醋酸酯，杂食卷叶蛾性信息素；E-4-十三烯醇醋酸酯，番茄针孔螟性信息素的主要成分；E,E-8,10-十二二烯醇，苹果蛾性信息素。这些合成通常采用I-IV类交换催化剂，步骤较少，使用通常易得的起始物质，并具有相对较短的工艺时间。这些合成产量良好，无需昂贵或复杂的设备。该发明还提供了通过交叉交换α-Ω-二乙酰基烯烃和α-Ω-二卤代烃来产生Ω-卤代烯醇的廉价途径，后者可以在传统的氢化方法下轻松转化为Ω-卤代烷醇。
• Perfume composition and process for producing the same
  申请人：——

  公开号：US20030157228A1

  公开（公告）日：2003-08-21

  The invention relates to a flavoring composition having a better milk-like flavor and a process for producing the composition. The composition comprises a 5-alkenoic acid and/or a 6-alkenoic acid both represented by general formula (1) and a lower aliphatic aldehyde having not greater than 8 carbon atoms: 1 wherein n is an integer of from 1 to 4, and the dashed line represents the presence of a carbon-carbon double bond at either side. The composition may further comprise a &dgr;-lactone represented by general formula (2) and/or a &ggr;-lactone represented by general formula (3): 2 wherein n is an integer of from 1 to 4; and 3 wherein n is an integer of from 1 to 4.

  本发明涉及一种具有更好的牛奶味的调味组合物和制备该组合物的方法。该组合物包括由一般式（1）表示的5-烯酸和/或6-烯酸以及具有不超过8个碳原子的低级脂肪醛：其中n是1到4的整数，虚线表示在任一侧存在碳-碳双键。该组合物还可以包括由一般式（2）表示的&dgr;-内酯和/或由一般式（3）表示的&ggr;-内酯：其中n是1到4的整数；和其中n是1到4的整数。
• PERFUME COMPOSITION AND PROCESS FOR PRODUCING THE SAME
  申请人：SODA AROMATIC COMPANY, LIMITED

  公开号：EP1396534A1

  公开（公告）日：2004-03-10

  The invention relates to a flavoring composition having a better milk-like flavor and a process for producing the composition. The composition comprises a 5-alkenoic acid and/or a 6-alkenoic acid both represented by general formula (1) and a lower aliphatic aldehyde having not greater than 8 carbon atoms: wherein n is an integer of from 1 to 4, and the dashed line represents the presence of a carbon-carbon double bond at either side. The composition may further comprise a δ-lactone represented by general formula (2) and/or a γ-lactone represented by general formula (3): wherein n is an integer of from 1 to 4; and wherein n is an integer of from 1 to 4.

  本发明涉及一种具有更好的牛奶香味的调味组合物以及生产该组合物的工艺。该组合物由通式（1）代表的 5-烯酸和/或 6-烯酸以及碳原子数不大于 8 的低级脂肪醛组成： 其中 n 为 1 至 4 的整数，虚线表示两侧存在碳碳双键。组合物可进一步包含通式（2）代表的 δ-内酯和/或通式（3）代表的 γ-内酯： 其中 n 为 1 至 4 的整数；以及 其中 n 为 1 至 4 的整数。
• Vinczer, Peter; Novak, Lajos; Szantay, Csaba, Organic Preparations and Procedures International, 1991, vol. 23, # 4, p. 443 - 447
  作者：Vinczer, Peter、Novak, Lajos、Szantay, Csaba

  DOI：——

  日期：——
• Enzymes in organic synthesis. 27. Lipase-Catalyzed Synthesis of (5R,6S)-6-Acetoxyalkan-5-olides - homologues of the mosquito oviposition attractant pheromone
  作者：B. Henkel、A. Kunath、Hans Schick

  DOI：10.1002/prac.19973390176

  日期：——

  Sixteen homologous (5R*,6S*)-6-hydroxyalkan-5-olides rac-5 and their acetoxy derivatives rac-6 were synthesized from the corresponding methyl (Z)-alk-5-enoates 3 by osmium(VIII) oxide catalyzed cis-hydroxylation to the dihydroxy esters rac-4 and hydrolysis of these esters followed by lactonization. Pancreatin-catalyzed lactonization of the dihydroxy esters rac-4 afforded enantiomerically enriched hydroxy lactones ent-5, five of which were obtained enantiomerically pure by recrystallization. Acetylation of the 6-hydroxyalkan-5-olides rac-5 by vinyl acetate catalyzed by the lipase SP 526 provided enantiomerically enriched 6-acetoxyalkan-5-olides 6 with an enantiomeric excess of more than 90% in nine cases. These compounds are known as mosquito oviposition attractant pheromone (6h) or its homologues.