N-isobutyl (2E,4E,8Z)-unadeca-2,4,8-trienamide

• 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: N-isobutyl (2E,4E,8Z)-unadeca-2,4,8-trienamide
• 英文别名: (2E,4E,8Z)-N-isobutylundeca-2,4,8-trienamide；N-isobutyl E2,E4,Z8-undecatrienamide；(2E,4E,8Z)-N-(2-methylpropyl)undeca-2,4,8-trienamide
• 化学式: C₁₅H₂₅NO
• 分子量: 235.37
• InChiKey: APJKFOYYKOIUJP-NDYRIVJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  6-壬烯醛 在 正丁基锂 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 三苯基膦 、 sodium hydroxide 、 苯酚 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 甲苯 、 乙腈 为溶剂， 反应 74.0h， 生成 N-isobutyl (2E,4E,8Z)-unadeca-2,4,8-trienamide
  参考文献：
  名称：

  Bungeanool、Isobungeanool、Dihydrobungeanool、Tetrahydrobungeanool、Hazaleamide、Lanyuamide III 和类似物的合成

  摘要：

  花椒是从花椒果皮中分离得到的一族醇酰胺类天然产物，在结构上与花椒有亲缘关系。虽然 sanshools，尤其是羟基-α-sanshool，已在各种背景下进行了研究，但关于 bungeanools 的研究却非常有限。为了促进他们的研究，我们通过使用也适用于合成类似物的灵活路线开发了该化合物家族所有四个成员的立体选择性合成。合成中的关键转化是立体选择性三苯基膦/苯酚催化的炔酸酯异构化为相应的共轭 E,E-二烯酸酯。

  DOI：

  10.1055/a-1653-4050

文献信息

• [EN] FLAVOURANT COMPOUNDS<br/>[FR] COMPOSANTS AROMATIQUES
  申请人：GIVAUDAN SA

  公开号：WO2004011415A1

  公开（公告）日：2004-02-05

  Use as a flavour ingredient of an aliphatic or aromatic unsaturated amide of formula (I).

  作为化学式（I）的脂肪族或芳香族不饱和酰胺的风味成分。
• E2,E4,Z8-undecatrienoic acid and ester and carboxamide derivatives thereof, organoleptic uses thereof and processes for preparing same
  申请人：Dewis L. Mark

  公开号：US20050197387A1

  公开（公告）日：2005-09-08

  Described is a genus of undecatrienoic acid derivatives useful in imparting, augmenting and/or enhancing flavors, aromas and somatosensory effects in or to consumable materials such as foods, beverages, skin care products, oral care products, medicinal products and the like. Also described is a synthesis process for producing such derivatives.

  本文描述了一种十一烯三酸衍生物的属，可用于赋予、增强和/或提高可食用材料（如食品、饮料、皮肤护理产品、口腔护理产品、药品等）的味道、香气和体感效果。同时还描述了一种用于生产这种衍生物的合成过程。
• E2, E4,Z8-Undecatrienoic acid and ester and carboxamide derivatives thereof, organoleptic uses thereof and processes for preparing same
  申请人：INTERNATIONAL FLAVORS & FRAGRANCES INC.

  公开号：EP1496042B1

  公开（公告）日：2009-11-11
• Use of a liquid cooling sensate to provide a pungent, warming or tingling sensate composition
  申请人：Moza Ashok K

  公开号：US20080038386A1

  公开（公告）日：2008-02-14

  The present invention is directed to a sensate composition consisting of a liquid cooling composition, and at least one warming, tingling, or pungent sensate ingredient of either synthetic or natural origin which provides enhanced warming, tingling, or pungent properties. The liquid cooling sensate of the invention is a eutectic mixture of 2-Isopropyl-N,2,3-trimethylbutyramide and N-Ethyl-p-menthane-3-carboxamide, or at least one cooling agent selected from the group consisting of N-(2-hydroxyethyl)-2,3-dimethyl-2-isopropylbutanamide, N-(3-ethoxypropyl)-2,3-dimethyl-2-isopropylbutanamide, N-(3-isopropoxypropyl)-2,3-dimethyl-2-isopropylbutanamide, N-(3-butoxypropyl)-2,3-dimethyl-2-isopropylbutanamide,N-Ethyl-2,2-diisopropylbutanamide, N-(1,1-dimethyl-2-hydroxyethyl)-2,2-diethylbutanamide, N-(2-ethoxyethyl)-2,3-dimethyl-2-isopropylbutanamide and N-(3-methoxypropyl)-2,3-dimethyl-2-isopropylbutanamide. The warming, tingling, or pungent sensate of the invention consists of at least one component that is an isothiocyanate and/or an amide or a natural product that contains at least one warming, tingling, or pungent principle that is an isothiocyanate and/or an amide. The present invention is further directed to a method of using the sensate composition in a food, pharmaceutical or personal care product.