2,7-二甲基辛-6-烯醛 | 111396-28-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,7-二甲基辛-6-烯醛
• 英文名称: (2RS)-2,7-Dimethyloct-6-enal
• 英文别名: 2,7-dimethyloct-6-enal；2,7-dimethyl-6-octenal；6-Octenal, 2,7-dimethyl-
• CAS: 111396-28-2
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: RRPLNOVWTWPBFK-UHFFFAOYSA-N

物化性质

• 沸点：
  208.4±9.0 °C(Predicted)
• 密度：
  0.835±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  2,7-二甲基辛-6-烯醛 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.83h， 以86%的产率得到(2RS)-2,7-Dimethyloct-6-en-1-ol
  参考文献：
  名称：

  一种实用的Domino-Claisen-Cope序列，用于合成新盛开的柑橘和强效的花香玫瑰醇。

  摘要：

  在艾伦·弗朗西斯·托马斯（Alan Francis Thomas）首次发现五十年之后，我们描述了一种多用途，无金属且无压力的多米诺-克莱森-科普重排方法，它使用易于获得的α，β-不饱和醛5或其缩醛5'和烯丙基醇6进行重排。通过这种转换，可以方便地访问大量的辐射柑橘和花香的玫瑰味气味剂。气味新颖花香红润和柑橘醇的型材13，14，和16进行了研究。化合物14ba具有花香，玫瑰色，天竺葵般的特征，并具有独特的性能和扩散性。复合16ba具有清晰的主要柑橘香气特征，具有干净的绿色葡萄柚/大黄成分。两种香精最近已成功引入Rosyfolia ™（14ba）和Pomelol ™（16ba）香水中。

  DOI：

  10.1002/hlca.201700200
• 作为产物：
  描述：

  Citronellsaeuremethylester 在 lithium aluminium tetrahydride 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 various solvent(s) 为溶剂， 反应 6.25h， 生成 2,7-二甲基辛-6-烯醛
  参考文献：
  名称：

  Intra- and intermolecular hetero-Diels-Alder reactions. 45. Simple and induced diastereoselectivity in intramolecular hetero-Diels-Alder reactions of 1-oxa-1,3-butadienes. Experimental data and calculations

  摘要：

  The simple and induced diastereoselectivity of the intramolecular hetero-Diels-Alder reaction of the alkylidene 1,3-dicarbonyl compounds 7a-e, obtained in situ by Knoevenagel condensation of the aldehydes 5a-e and dimethylbarbituric acid 6, was investigated experimentally and theoretically. In all examples the selectivity is very high; thus the domino reaction of 5a and 6 gives nearly exclusively the trans-fused tricyclic dihydropyran 8 (trans/cis = 98.8:1.2). In the similar reactions of the chiral aldehydes 5b-e and 6 the trans-cycloadducts 28, 33, 36, and 41 are the main products out of four possible diastereomers. The induced diastereoselectivity for the reaction of 5b and 5e with 6 is >99:1 and for the reaction of 5e and Sd-with 6, 95.2:3.6 and 94.1:4.7, respectively. Semiempirical AM1 calculations have been used to locate the transition structures of the intramolecular hetero-Diels-Alder reaction of 7a. The results were employed to create new parameters for the MM2-type force-field to determine the transition structures of 7b-e. The obtained data were compared with the experimental results of the cycloadditions and showed an excellent agreement.

  DOI：

  10.1021/jo00080a030

文献信息

• Synthesis of 3‐substituted indoles promoted by pulverization‐activation method catalyzed by Bi(NO ₃ ) ₃ ·5H ₂ O
  作者：Mohammad M. Khodaei、Parvin Ghanbary、Iraj Mohammadpoor‐Baltork、Hamid R. Memarian、Ahmad R. Khosropour、Kobra Nikoofar

  DOI：10.1002/jhet.5570450213

  日期：2008.3

  A new, facile, efficient, “green” and chemoselective procedure for the synthesis of indole derivatives has been developed with pulverization-activation method catalyzed by Bi(NO3)3·5H2O (PAMC- Bi(NO3)3·5H2O) through grinding of indoles with aldehydes or Michael acceptors in the presence of catalytic amounts of Bi(NO3)3·5H2O under solvent-free conditions.

  利用Bi（NO 3）3 ·5H 2 O（PAMC- Bi（NO 3）3 ·5H 2 O）通过在催化量的铋（存在NO与醛或迈克尔受体的吲哚的磨削3）3 ·5H 2 ö无溶剂下的条件。
• A novel, short and efficient synthesis of divinyl ethers
  作者：Mukund G Kulkarni、Aniruddha K Doke、Saryu I Davawala、Ajit V Doke

  DOI：10.1016/s0040-4039(03)01079-7

  日期：2003.6

  An efficient one-step synthesis of divinyl ethers from aldehydes and ketones using Wittig olefination is described.

  描述了使用维蒂希烯化反应由醛和酮有效一步合成二乙烯基醚的方法。
• Synthesis of 4-halotetrahydropyrans from allylsilanes and carbonyl compounds in the presence of lewis acids
  作者：Laura Coppi、Alfredo Ricci、Maurizio Taddei

  DOI：10.1016/s0040-4039(00)95890-8

  日期：1987.1

  An unexpected behavior of the reaction of allylsilanes and carbonylcompounds allowed the stereospecific preparation of differently substituted 4-halotetrahydropyrans with an “all cis” configuration.

  烯丙基硅烷与羰基化合物反应的出乎意料的行为允许立体异构地制备具有“全顺式”构型的不同取代的4-卤代四氢吡喃。
• GAS–LIQUID CHROMATOGRAPHY OF TERPENES: PART IX. THE VOLATILE OIL OF THE LEAVES OF JUNIPERUS SABINA L.
  作者：E. Von Rudloff

  DOI：10.1139/v63-421

  日期：1963.11.1

  The chemical composition of the volatile oil of the leaves of local savin juniper and of commercial oil of savin was determined by an improved gas chromatographic technique. Both oils contain d-sabinyl acetate (38, 37.5%) and d-sabinene (30.5, 26%) as the major constituents. Smaller amounts of d,α-pinene, d-myrcene, d-limonene, γ-terpinene, p-cymene, d-isothujone, d-terpinen-4-ol, d-sabinol, d-citronellol, d-cadinene, and l-elemol were isolated. Trace amounts of α-thujene, camphene, α-terpinene, 1,8-cineole, terpinolene, thujone, geraniol, a cadinene isomer, and δ-cadinol were tentatively identified. A fraction having the typical pungent odor of juniper leaves was isolated, but it was found to consist mainly of the methyl ester of d-citronellic acid. Several unidentified oxygenated sesquiterpenes and a phenol ether were isolated in trace amounts.Some phylogenetic relationships with other thujone-bearing oils analyzed in this series are discussed.

  通过改进的气相色谱技术，确定了当地青柏叶挥发油和商业青柏油的化学成分。两种油都含有d-香树酸乙酯（38％，37.5％）和d-香树烯（30.5％，26％）作为主要成分。还分离出少量的d，α-蒎烯，d-肉豆蔻烯，d-柠檬烯，γ-松节油烯，对甲酚，d-异硫松油酮，d-松节醇，d-香茅醇，d-卡丁烯，和l-顺-2-己烯醇。尝试鉴定微量的α-油松烯，蒎烯，α-松节油烯，1,8-桉叶醇，松油烯，松脑，香叶醇，卡丁烯同分异构体和δ-卡丁烯醇。分离出具有典型杜松叶辛辣气味的一部分，但发现它主要由d-柠檬酸甲酯组成。还分离了一些未知的含氧倍半萜和酚醚化合物的微量物质。讨论了与本系列中分析的其他含蒎烯油的植物的一些系统发育关系。
• Photo-driven metal-free multicomponent reaction between aldehydes, anilines and 4-substituted-DHPs for the synthesis of secondary amines
  作者：Zhen Yao、Ji Yang、Zhenli Luo、Heyu Wang、Xin Zhang、Jianhan Ye、Lijin Xu、Qian Shi

  DOI：10.1039/d2gc02613a

  日期：——

  readily available aldehydes, primary amines and 4-alkyl-1,4-dihydropyridines (alkyl-DHPs) for the synthesis of secondary amines at room temperature under visible light irradiation has been accomplished. This transformation occurs smoothly under mild conditions to enable facile access to various secondary amines with high efficiency, wide substrate scope and good functional group tolerance, and can be

  已经完成了一种容易获得的醛、伯胺和 4-烷基-1,4-二氢吡啶 (烷基-DHP) 的无光催化剂和无过渡金属多组分反应，用于在室温下在可见光照射下合成仲胺。这种转化在温和的条件下顺利进行，可以轻松获得各种仲胺，具有高效率、宽底物范围和良好的官能团耐受性，并且易于放大。溶剂的选择对反应结果有很大影响，而 CHCl 3被证明是最佳的。此外，该良性协议的合成效用通过其在医学相关复杂分子的后期功能化中的应用得到进一步展示。

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