(2Z,4E)-3,7-dimethyl-2,4,6-octatrienal | 49831-80-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2Z,4E)-3,7-dimethyl-2,4,6-octatrienal
• 英文别名: (2Z)-dehydrocitral；(2Z,4E)-3,7-dimethyl-octa-2,4,6-trienal；trans-4,5-didehydro-neral；(2Z,4E)-3,7-dimethylocta-2,4,6-trienal
• CAS: 49831-80-3
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: UDYGWSPUYSRWRN-JSRXJHBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-甲基-2-丁烯酸乙酯 在 manganese(IV) oxide 、 sodium hydride 、 二异丁基氢化铝 作用下， 反应 6.5h， 生成 (2Z,4E)-3,7-dimethyl-2,4,6-octatrienal
  参考文献：
  名称：

  Factors affecting the absorption maxima of polyene iminium systems: a model study for rhodopsin and bacteriorhodopsin

  摘要：

  DOI：

  10.1021/ja00350a048

文献信息

• Synthese von Diterpenen als mögliche biogenetische Vorläufer des C₂₀-Carotinoides Crocetin
  作者：Heidi Schurtenberger、Ulrich Vögeli、Hanspeter Pfander

  DOI：10.1002/hlca.19830660746

  日期：1983.11.2

  Synthesis of Diterpenes as Possible Biogenetic Precursors of the C20-Carotenoid Crocetin

  二萜类化合物的合成可能是C 20-类胡萝卜素藏花色素的生物遗传前体。
• Methods for preparing aldehydes by self-aldol condensation
  申请人：Babler James H.

  公开号：US20090270658A1

  公开（公告）日：2009-10-29

  Methods for preparing self-aldol condensation products of prenyl aldehyde (3-methyl-2-butenal) by use of an amine catalyst under weakly acidic conditions at temperatures of 10° C. or higher are disclosed. Methods are disclosed for the selective formation of α-1,2-adducts and γ-1,2-adducts of prenyl aldehyde, and for the formation of specialty compositions useful in the flavor and fragrance industries.

  使用胺催化剂在弱酸性条件下，在10°C或更高温度下制备异戊醛（3-甲基-2-丁烯醛）的自身醛缩产物的方法被披露。还披露了用于选择性形成异戊醛的α-1,2-加合物和γ-1,2-加合物的方法，以及用于制备在风味和香料行业中有用的特殊组合物的方法。
• Prenylation Reaction Performed with Catalytically Generated Potassium Prenal Dienolate
  作者：Dominique Cahard、Lucette Duhamel、Sandrine Lecomte、Jean-Marie Poirier

  DOI：10.1055/s-1998-1955

  日期：1998.12

  A new prenylation method based on the reaction of catalytically generated potassium dienolate of prenal with α,β-unsaturated aldehydes is described. The reaction is highly regioselective, via a γ-1,2-addition, and provides an efficient route to retinal.

  本文介绍了一种新的预炔化方法，该方法基于催化生成的预炔二烯酸钾与δ、δ²-不饱和醛的反应。该反应通过δ-1,2-加成具有高度的区域选择性，并提供了获得视黄醛的有效途径。
• (4E)-Dehydrocitrals [(2E,4E)- and (2Z,4E)-3,7-dimethyl-2,4,6-octatrienals] from Acarid Mite Histiogaster sp. A096 (Acari: Acaridae)
  作者：Hiroyuki HIRAOKA、Naoki MORI、Ritsuo NISHIDA、Yasumasa KUWAHARA

  DOI：10.1271/bbb.65.2749

  日期：2001.1

  A mixture of two monoterpenes was obtained as the opisthonotal gland secretion from unidentified Histiogaster sp. A096 (Acari: Acaridae), and their structures were elucidated to be (4E)-dehydrocitrals[(2E,4E)- and (2Z,4E)-3,7-dimethyl-2,4,6-octatrienals] by GC/MS, GC/FT-IR, UV and 1H-NMR spectra. Both isomers of (4E)-dehydrocitral prepared by syntheses in 4 steps from 3-methyl-2-butenal with 34.2% yields (based on the ylide) were separated by column chromatography into the (2E,4E)- and (2Z,4E)-3,7-dimethyl-2,4,6-octatrienal. Mass spectra together with GC retention times of the purified natural (4E)-dehydrocitrals were identical with those of synthetic (2E,4E)-3,7-dimethyl-2,4,6-octatrienal and (2Z,4E)-3,7-dimethyl-2,4,6-octatrienal. The geometry at the 2-C position of both synthetic (4E)-dehydrocitrals was confirmed by NOESY analyses. This is the first identification of (4E)-dehydrocitrals from the animal kingdom.

  从未鉴定的Histiogaster sp. A096（蜱目：蜱科）获得的后背腺分泌物中得到了一种混合的双萜烯，其结构通过气相色谱-质谱（GC/MS）、气相色谱-傅里叶变换红外光谱（GC/FT-IR）、紫外光谱（UV）和氢核磁共振谱（1H-NMR）被阐明为（4E）-去氢柠檬醛[(2E,4E)-和(2Z,4E)-3,7-二甲基-2,4,6-辛三烯醛]。这两种（4E）-去氢柠檬醛的异构体通过四步从3-甲基-2-丁醛合成，产率为34.2%（基于超烯），并通过柱色谱分离为(2E,4E)-和(2Z,4E)-3,7-二甲基-2,4,6-辛三烯醛。纯化后的天然（4E）-去氢柠檬醛的质谱及其气相色谱保留时间与合成的(2E,4E)-3,7-二甲基-2,4,6-辛三烯醛和(2Z,4E)-3,7-二甲基-2,4,6-辛三烯醛相同。通过NOESY分析确认了两种合成（4E）-去氢柠檬醛在2-C位的几何构型。这是首次在动物界中鉴定出（4E）-去氢柠檬醛。
• Polyvinylogation reagents : 1-lithio-4-trimethylsiloxy-penta-1,3-diene and 1-lithio-4-ethoxy-2-methyl-buta-1,3-diene
  作者：Lucette Duhamel、Jean-Erick Ancel

  DOI：10.1016/s0040-4020(01)85614-3

  日期：1992.1

  Title products, lithiodienol ethers 6a and 7a, synthetic equivalents of 4-lithio pent-3-ene-2-one and 4-lithio-senecialdehyde were obtained by bromine-lithium exchange. They are choice reagents for the transformations l --> 2 and l --> 3, respectively.