(3S,6R)-3-methyl-6-(1-methylethyl)cyclohexene | 5056-00-8

• 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: (3S,6R)-3-methyl-6-(1-methylethyl)cyclohexene
• 英文别名: (+)-trans-p-menth-2-ene；(-)trans-p-menth-2-ene；(+)-trans-p-menthene；(1R,4R)-2-menthene；trans-2-p-menthene；cis-menth-2-ene；trans-p-Menth-2-ene；(3S,6R)-3-methyl-6-propan-2-ylcyclohexene
• CAS: 5056-00-8
• 化学式: C₁₀H₁₈
• 分子量: 138.253
• InChiKey: WHNGPXQYYRWQAS-NXEZZACHSA-N

物化性质

• 沸点：
  165.2±7.0 °C(Predicted)
• 密度：
  0.804±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (3S,6R)-3-methyl-6-(1-methylethyl)cyclohexene 在 sodium periodate 、 间氯过氧苯甲酸 、 potassium hydroxide 作用下， 生成 2-isopropyl-5-methyladipaldehyde
  参考文献：
  名称：

  Acid-catalyzed aldol-Meerwein–Ponndorf–Verley-etherification reactions—access to defined configured quaternary stereogenic centers

  摘要：

  A novel asymmetric aldol-reduction-etherification process of aliphatic enolizable aldehydes is described. The intermediately formed aldol adducts-beta-hydroxyaldehydes-were reduced and transformed into the corresponding 1,3-diol ethers by external secondary alcohols at the same time. Thus, with the help of chiral secondary alcohols an access to optically active 1,3-diol ether is given. Furthermore, asymmetric cross-aldol-Meerwein-Ponndorf reactions of enolizable aldehydes can also be realized under these reaction conditions. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.069
• 作为产物：
  描述：

  在 Li₂Cu₃Me₅ 作用下， 以 乙醚 为溶剂， 反应 15.0h， 以81%的产率得到(3S,6R)-3-methyl-6-(1-methylethyl)cyclohexene
  参考文献：
  名称：

  顺式和反式3-甲基-6-甲基乙基环己烯和3-甲基-4-甲基乙基环己烯的区域和立体定向合成。烯丙基乙酸酯和氨基甲酸酯与Li 2 Cu 3 Me 5和LiCuMe 2的反应

  摘要：

  异构烯烃1-4是通过用Li 2 Cu 3 Me 5对适当的烯丙基氨基甲酸酯进行γ合成，γ取代而获得的。氨基甲酸酯的行为深受铜试剂性质的影响。

  DOI：

  10.1016/s0040-4039(00)87541-3

文献信息

• Copper-Mediated and -Catalyzedo-DPPB-Directed Allylic Substitution
  作者：Bernhard Breit、Peter Demel

  DOI：10.1002/1615-4169(200107)343:5<429::aid-adsc429>3.0.co;2-k

  日期：2001.7

  Complete control of chemo-, regio- and stereoselectivity in the course of copper-catalyzed and -mediated allylic substitution could be obtained with the ortho-diphenylphosphanyl (o-DPPB) function as a reagent-directing leaving group. Complete chirality transfer by way of a syn-addition process has been achieved for cyclic and acyclic systems. Readily available Grignard reagents may be employed as nucleophiles

  以邻-二苯基膦烷基（o- DPPB）为试剂导向离去基团，可以在铜催化和介导的烯丙基取代过程中完全控制化学，区域和立体选择性。对于循环系统和非循环系统，已经通过合成加成方法实现了完全手性转移。可以将现成的格氏试剂用作亲核试剂，并且可以定量回收指向o- DPPB的基团。该反应既不需要冷却也不需要过量的有机金属试剂。
• Practical Synthesis of Optically Pure Menthylamines Starting from Racemic Neomenthol
  作者：Siegfried Waldvogel、Nina Welschoff

  DOI：10.1055/s-0030-1258295

  日期：2010.11

  scalable route to racemic and highly enantiomerically enriched menthylamines exploits the technical product rac-neomenthol as the starting material. The elaborated protocol is based on nucleophilic substitution of the hydroxy moiety by azide. Subsequent reduction and resolution with tartaric acid provides the desired optically enriched menthylamines. amines - azides - chiral resolution - reduction - terpenoids

  可靠的，可扩展的途径生产外消旋和高度对映异构体富集的薄荷胺，采用了技术产品外消旋-薄荷脑作为原料。精心设计的方案基于叠氮化物对羟基部分的亲核取代。随后用酒石酸还原和拆分得到所需的光学富集的薄荷胺。 胺-叠氮化物-手性拆分-还原-萜类化合物
• o-DPPB-Directed Copper-Mediated and -Catalyzed Allylic Substitution with Grignard Reagents
  作者：Peter Demel、Manfred Keller、Bernhard Breit

  DOI：10.1002/chem.200600225

  日期：2006.8.25

  explored as a directing leaving group in copper-mediated and copper-catalyzed allylic substitution with Grignard reagents. Complete control of chemo-, regio- and stereoselectivity with complete syn-1,3-chirality transfer was observed as a result of the directed nature of the reaction. No excess of organometallic reagent is required and the directing group can be recovered quantitatively. Coordination

  研究了邻二苯基膦基苯甲酰基（o-DPPB）基团作为用格氏试剂在铜介导的和铜催化的烯丙基取代中的直接离去基团。作为反应的定向性质的结果，观察到化学，区域和立体选择性的完全控制以及syn-1,3-手性的完全转移。不需要过量的有机金属试剂，并且可以定量回收导向基团。在固态和溶液中的配位研究表明，两个底物通过铜上导向基团的膦功能键合。溶液中的动态NMR实验与铜的配位体交换过程相一致，这是发展亚化学计量过程的前提。
• Synthesis and Sensory Studies of Umami-Active Scaffolds
  作者：Michael Backes、Susanne Paetz、Tobias Vössing、Jakob Peter Ley

  DOI：10.1002/cbdv.201400113

  日期：2014.11

  molecules. A scalable synthesis of this challenging scaffold and new sensory insights will be presented. Interestingly, the umami characteristics differ remarkably, depending on constitutional and stereochemical features of the parent scaffold. During our studies, we could identify the carboxamide moiety as a crucial factor to influence the umami intensity of these scaffolds. In addition, the configuration

  2-异丙基-5-甲基双环[4.1.0]庚烷-7-甲酰胺类，1-4，已被鉴定为有效的鲜味分子。将介绍这种具有挑战性的支架和新的感官洞察力的可扩展合成。有趣的是，鲜味特征显着不同，这取决于母体支架的构成和立体化学特征。在我们的研究中，我们可以确定羧酰胺部分是影响这些支架鲜味强度的关键因素。此外，环丙基部分的构型会产生一些影响，而薄荷基支架的绝对构型，至少是测试的 D 和 L 构型，则不太重要。
• Optical Rotatory Dispersion and Circular Dichroism of the Osmate Esters of Cyclic Mono-olefins
  作者：Naokazu Sakota、Shunsaku Tanaka

  DOI：10.1246/bcsj.44.485

  日期：1971.2

  The osmate esters (as the di-pyridine adducts) of optically active mono-, di- and tricyclic mono-unsaturated terpenes were prepared for measurements of optical rotatory dispersion (ORD) and circular dichroism (CD). All the osmate esters of the cyclic olefins examined exhibited a strong Cotton effect in 470 mμ regions and a weak Cotton effect near 600 mμ regions, which were similar to those of the osmate

  制备旋光性单、二和三环单不饱和萜烯的锇酸酯（作为二吡啶加合物）用于旋光色散 (ORD) 和圆二色性 (CD) 的测量。环烯烃的所有锇酸酯在 470 mμ 区域表现出强烈的棉花效应，在 600 mμ 区域附近表现出弱的棉花效应，这与我们之前的论文中报道的开链烯烃的锇酸酯相似。发现 470 mμ 区域中 CD 最大值的符号与包含锇发色团的螯合环的 gauche 结构的手性相关。此外，它们的绝对构型是从顺式-α-蒎烯二醇的两种非对映异构体的圆二色性数据推导出来的。

表征谱图