2,2-dimethyl-octanal | 14250-91-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dimethyl-octanal
• 英文别名: 2,2-Dimethyloctanal
• CAS: 14250-91-0
• 化学式: C₁₀H₂₀O
• 分子量: 156.268
• InChiKey: KVGYAHNHKCCHSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-octanal 在 六甲基磷酰三胺 、 lithium hydroxide 、 正丁基锂 、 草酰氯 、 N,N-二甲基甲酰胺 、 六甲基二硅氮烷 作用下， 以 甲醇 、 苯 为溶剂， 反应 3.5h， 生成 (5Z,8Z,11Z,14Z)-16,16-dimethyldocosa-5,8,11,14-tetraenoyl chloride
  参考文献：
  名称：

  Potent Anandamide Analogs:  The Effect of Changing the Length and Branching of the End Pentyl Chain

  摘要：

  To examine the effect of changing the length and branching of the end pentyl chain (C5H11) of anandamide (AN), various analogs 1a-h and 2a-f were synthesized from either the known aldehyde ester 6a or from the alcohol 6b and tested for their pharmacological activity. A reproducible procedure was developed for the conversion of arachidonic acid to 6a or 6b in gram quantities (overall yield 15%). The appropriate tetraene esters 7 were prepared by carrying out a Wittig reaction, between 6a and the ylide generated from the phosphonium salt of the appropriate alkyl halide or between the ylide of 6d (prepared from 6a --> 6b --> 6c --> 6d) and the appropriate alkyl aldehydes. They were then hydrolyzed to the corresponding acids and transformed into AN analogs 1 via their acid chlorides then treated with excess ethanolamine. alpha-Alkylation of esters 7 gave compounds 8 which were hydrolyzed to the corresponding acids. These acids via their acid chlorides and subsequent treatment with excess fluoroethylamine gave the target compounds 2. In this way analogs 1e and 2a-c were synthesized from 6d while all the remaining analogs were prepared from 6a. In order to assess the optimal length of the alkyl terminus, analogs 1a-d were prepared and showed moderately high affinities (18-55 nM). However analogs 1a-c failed to produce significant pharmacological effects at doses up to 30 mg/kg. Analog 1d was found to be a weak partial agonist. The reason for the lack of activity in 1a-c is presently not clear. Like the THCs, the branching of the end pentyl chain in AN (1e-h) increased potency both in in vitro and in vivo activities; the dimethylheptyl (DMH) analog 1e was the most potent in the series. Similar alkyl substitutions were carried out in the fluoro-2-methylanandamide series (2a-f), and all of these analogs had high receptor affinities (1-14 nM), the DMH analog 2a being the most potent. With a few exceptions they showed robust pharmacological effects, and AN-like profiles, It was shown that the SAR of the end pentyl chain in AN is very similar to that of THCs. However, the magnitude of enhanced potency observed when the side chain of THC was changed from straight to branched was not observed when the end chain of AN was similarly changed.

  DOI：

  10.1021/jm970212f
• 作为产物：
  描述：

  2,2-二甲基辛醇 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以86%的产率得到2,2-dimethyl-octanal
  参考文献：
  名称：

  Synthesis and Pharmacological Comparison of Dimethylheptyl and Pentyl Analogs of Anandamide

  摘要：

  (CH₂CH₃)₁₆-取代壬二烯酰胺醇胺（17a）及其酰胺类衍生物通过Wittig偶联反应合成，该偶联反应基于拉动奇族状酸丁酰胺的丁酰胺酸基团。这些酰胺类衍生物与内源性 cannabinoid 受体结合者 酯酸胆碱（anandamide，2a）及其酰胺类衍生物在药理学检测中对比分析，以考察其潜在的增强 Cannabinoid 模拟活性。在取代作用实验中，与相应的 anandamide（2a）及其酰胺类衍生物相比，DMH 类衍生物的受体亲和力显著提升（一个数量级），其与[H-3]CP55,940或[H-3]SR141716A相比，亲和力结果呈现出顺序差异。与 2a相比，在小鼠四联试验中进行的用于测试 Cannabinoid 活性时，17a的反应效力得以明显增强（数量级相仿或更高），在小鼠精巢中进行的用于测试 Cannabinoid 活性时，17a的反应效力并未出现任何明显增强。实验数据表明，经典植物类 cannabinoids 与 2a在构效关系上具有等价性，并说明多受体各或结合模式上的特性。

  DOI：

  10.1021/jm9702950

文献信息

• DIENAL COMPOUND AND FLAVOR COMPOSITION
  申请人：Takasago International Corporation

  公开号：US20210122693A1

  公开（公告）日：2021-04-29

  The present invention relates to: a novel dienal compound which has an aromatic odor useful for use as a compound flavor raw material or the like; and a flavor composition containing the dienal compound. The dienal compound according to the present invention is characterized by being represented by general formula (1): (wherein R represents an alkyl group having 8 to 10 carbon atoms; and a wavy line represents a cis form, a trans form, or a mixture of a cis form and a trans form).

  本发明涉及：一种新型二烯醛化合物，具有芳香气味，可用作化合物香料原料或类似物；以及含有该二烯醛化合物的香料组合物。根据本发明，该二烯醛化合物的特征在于由通式（1）表示：（其中R代表具有8至10个碳原子的烷基基团；波浪线表示顺式形式、反式形式或顺反混合形式）。
• Intramolekulare reaktionen von alkylcarbenen
  作者：W. Kirmse、G. Wächtershäuser

  DOI：10.1016/0040-4020(66)80102-3

  日期：1966.1

  Various branched alkylcarbenes have been generated by alkaline decomposition of the corresponding tosylhydrazones. The intramolecular insertion reactions of these carbenes (formation of cyclopropanes) proceed with appreciable discrimination which depends strongly on steric effects. The product ratios are consistently explained by a transition state with approximately planar (eclipsed) configuration

  通过相应的甲苯磺酰hydr的碱分解已经产生了各种支链的烷基卡宾。这些卡宾的分子内插入反应（环丙烷的形成）进行明显的区分，这很大程度上取决于空间效应。产物比率始终由具有卡宾-碳和碳-氢键的近似平面（偏光）构型的过渡态来解释。烷基卡宾的选择性随摩尔的增加而增加。重量
• [EN] ARTHROPOD CONTROLLING COMPOSITION<br/>[FR] COMPOSITION DE LUTTE CONTRE LES ARTHROPODES
  申请人：FIRMENICH & CIE

  公开号：WO2020239980A1

  公开（公告）日：2020-12-03

  The present invention relates to an arthropod controlling composition comprising a compound according to formula (I), methods and uses to control arthropods as well as arthropod controlling articles comprising the same.

  本发明涉及一种包括根据式(I)的化合物的节肢动物控制组合物，以及用于控制节肢动物的方法和用途，以及包含相同化合物的节肢动物控制物品。
• Single operation palladium catalysed C(sp³)–H functionalisation of tertiary aldehydes: investigations into transient imine directing groups
  作者：S. St John-Campbell、A. J. P. White、J. A. Bull

  DOI：10.1039/c7sc01218g

  日期：——

  Simple amine and diamine derivatives can promote the palladium catalysed direct β-C–H arylation of aliphatic aldehydes via transient imine formation. Trifluoroacetate was shown to be crucial in promoting the reaction. Sub-stoichiometric quantities of simple N-tosylethylenediamine was shown to form a bidentate directing group with an imine linkage. Isolation of an unsymmetrical palladacycle has shown

  简单的胺和二胺衍生物可以通过短暂的亚胺形成促进钯催化脂肪醛的直接β-CHH芳基化。已显示三氟乙酸盐对于促进反应至关重要。亚化学计量的简单N-甲苯磺酰基乙二胺已显示形成具有亚胺键的双齿引导基团。通过单晶X射线衍射分析，非对称palladacycle的分离显示了次级NTs配位基团的不同潜在结合模式，暗示了半不稳定的配体。
• [EN] 2,4-DIETHYLOCTA-2,6-DIENAL AND ITS USE AS AROMA CHEMICAL<br/>[FR] 2,4-DIÉTHYLOCTA-2,6-DIÉNAL ET SON UTILISATION COMME PRODUIT CHIMIQUE AROMATIQUE
  申请人：BASF SE

  公开号：WO2021122674A1

  公开（公告）日：2021-06-24

  The present invention relates to 2,4-diethylocta-2,6-dienal and a method of preparing same, to the use of 2,4-diethylocta-2,6-dienal as aroma chemical; to the use of 2,4-diethylocta-2,6- dienal for preparing an aroma chemical composition or for modifying the aroma character of an aroma chemical composition; to an aroma chemical composition containing 2,4- diethylocta-2,6-dienal; and to a method of preparing an aromatized composition or for modifying the aroma character of an aromatized composition.

  本发明涉及2,4-二乙基辛二烯醛及其制备方法，以及将2,4-二乙基辛二烯醛用作香料化学品的用途；将2,4-二乙基辛二烯醛用于制备香料化学品组合物或改变香料化学品组合物的香气特性的用途；含有2,4-二乙基辛二烯醛的香料化学品组合物；以及制备香味化合物或改变香味化合物的香气特性的方法。