(2RS)-2,7-Dimethyloct-6-en-1-ol | 153265-66-8

• 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: (2RS)-2,7-Dimethyloct-6-en-1-ol
• 英文别名: 2,7-dimethyloct-6-en-1-ol
• CAS: 153265-66-8
• 化学式: C₁₀H₂₀O
• 分子量: 156.268
• InChiKey: WDMOCGRCBAICQG-UHFFFAOYSA-N

物化性质

• 沸点：
  215.0±9.0 °C(Predicted)
• 密度：
  0.845±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2RS)-2,7-Dimethyloct-6-en-1-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 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
• 作为产物：
  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

文献信息

• 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
  作者：Lutz F. Tietze、Holger Geissler、Jens Fennen、Thomas Brumby、Siegbert Brand、Gerhard Schulz

  DOI：10.1021/jo00080a030

  日期：1994.1

  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.
• A Practical Domino-<i>Claisen-Cope</i>Sequence in the Synthesis of New Blooming Citrus and Potent Floral Rose Alcohols
  作者：Jie Liu、Yue Zou、Lijun Zhou、An Chai、Chao Wang、Hai-Shan Dang、Quanrui Wang、Andreas Goeke

  DOI：10.1002/hlca.201700200

  日期：2017.11

  Fifty years after its first discovery by Alan Francis Thomas, we describe a versatile, metal and pressure‐free domino‐Claisen–Cope rearrangement using the readily available α,β‐unsaturated aldehydes 5 or their acetals 5′ and allylic alcohols 6. This transformation provides a convenient access to a large number of radiant citrus and floral rosy odorants. Odor profiles of novel floral rosy and citrus

  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。