(E)-2,3,7-trimethylocta-2,6-dienoic acid ethyl ester | 72284-27-6

• 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: (E)-2,3,7-trimethylocta-2,6-dienoic acid ethyl ester
• 英文别名: ethyl (E)-2,3,7-trimethylocta-2,6-dienoate；(E)-ethyl 2,3,7-trimethylocta-2,6-dienoate；2.3.7-trimethyl-octadien-(2.6)-oic acid-(1)-ethyl ester；3.7-Dimethyl-octadien-(2.6)-carbonsaeure-(2)-aethylester；2.3.7-Trimethyl-octadien-(2.6)-saeure-(1)-aethylester；ethyl (E/Z)-2,3,7-trimethylocta-2,6-dienoate；ethyl (2E)-2,3,7-trimethylocta-2,6-dienoate
• CAS: 72284-27-6
• 化学式: C₁₃H₂₂O₂
• 分子量: 210.316
• InChiKey: MDHZSKWEFABKKL-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  (E)-2,3,7-trimethylocta-2,6-dienoic acid ethyl ester 在 二异丁基氢化铝 作用下， 反应 1.0h， 以90%的产率得到(2E)-2,3,7-trimethylocta-2,6-dien-1-ol
  参考文献：
  名称：

  2-甲基异冰片生物合成的立体化学过程

  摘要：

  使用 Sharpless 环氧化作为关键步骤，并通过手性固定相上的 HPLC 分离纯化对映体富集的中间体，对映体选择性地合成了 2-甲基芳樟基二磷酸 (2-Me-​​LPP) 的两种对映体。它们与 2-甲基异冰片合酶 (2MIBS) 的酶促转化表明 ( R )-2-Me-​​LPP 是通路中间体，而从 ( S )-2-Me-​​LPP形成少量 2-甲基异冰片可以解释异构化为 2-Me-​​GPP，然后异构化为 ( R )-2-Me-​​LPP。

  DOI：

  10.3762/bjoc.18.82
• 作为产物：
  描述：

  6-甲基-5-庚烯-2-酮 、 三乙基2-膦酰基丙酯 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以23%的产率得到(E)-2,3,7-trimethylocta-2,6-dienoic acid ethyl ester
  参考文献：
  名称：

  2-甲基异冰片生物合成的立体化学过程

  摘要：

  使用 Sharpless 环氧化作为关键步骤，并通过手性固定相上的 HPLC 分离纯化对映体富集的中间体，对映体选择性地合成了 2-甲基芳樟基二磷酸 (2-Me-​​LPP) 的两种对映体。它们与 2-甲基异冰片合酶 (2MIBS) 的酶促转化表明 ( R )-2-Me-​​LPP 是通路中间体，而从 ( S )-2-Me-​​LPP形成少量 2-甲基异冰片可以解释异构化为 2-Me-​​GPP，然后异构化为 ( R )-2-Me-​​LPP。

  DOI：

  10.3762/bjoc.18.82

文献信息

• [EN] SUBSTITUTED CYCLOPENTYL- AND CYCLOHEXYL-DERIVATIVES USEFUL FOR PERFUMERY<br/>[FR] DÉRIVÉS CYCLOPENTYLIQUES ET CYCLOHEXYLIQUES SUBSTITUÉS UTILES POUR LA PARFUMERIE
  申请人：GIVAUDAN SA

  公开号：WO2017097884A1

  公开（公告）日：2017-06-15

  The present invention refers to substituted cyclopentyl- and cyclohexyl-derivatives of formula (I) wherein n, R1, R2, R3, R4 and X have the same meaning as given in the description. The invention further refers to fragrance compositions and fragranced articles comprising them.

  本发明涉及式(I)的取代环戊基和环己基衍生物，其中n、R1、R2、R3、R4和X的含义与描述中给出的相同。该发明还涉及包含这些衍生物的香精组合物和带有香精的物品。
• Substituted cyclopentyl- and cyclohexyl-derivatives useful for perfumery
  申请人：Givaudan, S.A.

  公开号：US10640460B2

  公开（公告）日：2020-05-05

  The present invention refers to substituted cyclopentyl- and cyclohexyl-derivatives of formula (I) wherein n, R1, R2, R3, R4 and X have the same meaning as given in the description. The invention further refers to fragrance compositions and fragranced articles comprising them.

  本发明涉及式 (I) 的取代环戊基和环己基衍生物 其中 n、R1、R2、R3、R4 和 X 的含义与描述中给出的含义相同。 本发明还涉及香料组合物和由其组成的香料制品。
• Biochemistry and Molecular Genetics of the Biosynthesis of the Earthy Odorant Methylisoborneol in <i>Streptomyces coelicolor</i>
  作者：Chieh-Mei Wang、David E. Cane

  DOI：10.1021/ja803639g

  日期：2008.7.1

  Methylisoborneol (2) is a volatile organic compound produced by a wide variety of Actinomycetes soil orgainisms, myxobacteria, and cyanobacteria. It has an unusually low odor threshold and, together with geosmin, is responsible for the characteristics smell of moist soil as well as unpleasant taste and odor episodes assoiciated with public water supplies and contamination of various foodstuffs, including fish, wine and beer. Despite considerable interest in detection and remediation of methylisoborneal, the biosynthesis of this methylated monoterpene has been obscure. In Streptomyces coelicor, the sco7700 and sco7701 genes are shown to correspond to a two-gene operon responsible for methylisoborneol biosynthesis. Both genes have been amplified by PCR and the resulting DNA has been cloned and expressed in Escherichia coli. Incubation of recombinant SCO7701 protein, annotated as a possible C-methyltransferase, with geranyl diphosphate (1) and S-adenosylmethionine gave the previously unknown compound. (E)-2-methylgeranyl diphosphate (3). Incubation of 3 in the presence of Mg2+ with recombinant SCO7700, previously annotated only as a possible metal-binding protein or terpenoid synthase, resulted in the formation of 2-methylisoborneal (2). The steady-state kinetic parameters for both biochemical reactions have been determined. Incubation of geranyl diphosphate and S-adenosylmethionine with a mixture of both SCO7700 and SCO7701 resulted in formation of methylisoborneal (2). Cyclization of 2-methylgeranyl diphosphate (3) to methylisoborneal (2) likely involves the intermediacy of 2-methylinalyl diphosphate.
• Biosynthesis of the Off-Flavor 2-Methylisoborneol by the MyxobacteriumNannocystis exedens
  作者：Jeroen S. Dickschat、Thorben Nawrath、Verena Thiel、Brigitte Kunze、Rolf Müller、Stefan Schulz

  DOI：10.1002/anie.200702496

  日期：2007.11.5
• SUBSTITUTED CYCLOPENTYL- AND CYCLOHEXYL-DERIVATIVES USEFUL FOR PERFUMERY
  申请人：Givaudan S.A.

  公开号：EP3386940B1

  公开（公告）日：2019-10-16