(R)-1, -dimethoxy-2-methyl-5-(6-methylhept-5-en-2-yl)benzene | 670260-41-0

• 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: (R)-1, -dimethoxy-2-methyl-5-(6-methylhept-5-en-2-yl)benzene
• 英文别名: (R)-1,4-dimethoxy-2-methyl-5-(6-methylhept-5-en-2-yl)benzene；(R)-1-(2,5-dimethoxy-4-methylphenyl)ethyl diisopropylcarbamate；curcuhydroquinone dimethyl ether；1,4-dimethoxy-2-methyl-5-[(2R)-6-methylhept-5-en-2-yl]benzene
• CAS: 670260-41-0
• 化学式: C₁₇H₂₆O₂
• 分子量: 262.392
• InChiKey: KJKIXYMPCQWCMR-CYBMUJFWSA-N

物化性质

• 沸点：
  362.9±42.0 °C(Predicted)
• 密度：
  0.937±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-1, -dimethoxy-2-methyl-5-(6-methylhept-5-en-2-yl)benzene 在 ammonium cerium (IV) nitrate 、 甲基磺酰胺 、 AD-mix α 作用下， 以 水 、 乙腈 、 叔丁醇 为溶剂， 反应 23.5h， 生成 2-[(2R,5S)-5,6-dihydroxy-6-methylheptan-2-yl]-5-methylcyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  Enantioselective syntheses of the assigned structures of the helibisabonols A and B

  摘要：

  The enantioselective syntheses of the compounds with the assigned structures of the helibisabonols A and B have been accomplished. Using an enzymatic desymmetrization of the sigma-symmetrical diol (route a) and a diastereoselective conjugate addition of the methyl to the enone with a chiral auxiliary (route b) we constructed the key tertiary stereogenic center at the benzylic position (C7) and then used an asymmetric dihydroxylation for assembling the C10 stereogenic center. In addition, possible diastereoisomers of the natural products were prepared and detailed comparisons of the H-1 and C-13 NMR spectra were conducted. As a result, the structure originally assigned to helibisabonol A may be revised to (7R,10R)-1. In the case of helibisabonol B, the (7R,10R)-2 would be reasonable based on a comparison of the NMR data and the biogenetic parallelism with helibisabonol A. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.064
• 作为产物：
  描述：

  在 disodium hydrogenphosphate 、 sodium amalgam 、 正丁基锂 、 potassium hydrogencarbonate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 正己烷 、 二氯甲烷 为溶剂， 反应 13.33h， 生成 (R)-1, -dimethoxy-2-methyl-5-(6-methylhept-5-en-2-yl)benzene
  参考文献：
  名称：

  Enantioselective syntheses of the assigned structures of the helibisabonols A and B

  摘要：

  The enantioselective syntheses of the compounds with the assigned structures of the helibisabonols A and B have been accomplished. Using an enzymatic desymmetrization of the sigma-symmetrical diol (route a) and a diastereoselective conjugate addition of the methyl to the enone with a chiral auxiliary (route b) we constructed the key tertiary stereogenic center at the benzylic position (C7) and then used an asymmetric dihydroxylation for assembling the C10 stereogenic center. In addition, possible diastereoisomers of the natural products were prepared and detailed comparisons of the H-1 and C-13 NMR spectra were conducted. As a result, the structure originally assigned to helibisabonol A may be revised to (7R,10R)-1. In the case of helibisabonol B, the (7R,10R)-2 would be reasonable based on a comparison of the NMR data and the biogenetic parallelism with helibisabonol A. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.064

文献信息

• Application of the lithiation–borylation reaction to the rapid and enantioselective synthesis of the bisabolane family of sesquiterpenes
  作者：Varinder K. Aggarwal、Liam T. Ball、Simon Carobene、Rickki L. Connelly、Matthew J. Hesse、Benjamin M. Partridge、Philippe Roth、Stephen P. Thomas、Matthew P. Webster

  DOI：10.1039/c2cc32176a

  日期：——

  The expedient enantioselective synthesis of 5 bisabolane sesquiterpenes has been achieved using a common, one-pot lithiation-borylation reaction of secondary benzylic carbamates and either protodeboronation or oxidation to give the natural products in fewer than 5 steps, with high yield and >94 : 6 er.

  使用仲氨基甲酸苄酯的常见的一锅锂化-硼化反应以及原脱硼烷或氧化反应可在不到5个步骤的情况下以高收率和大于94：6的比例获得天然产物，从而实现了5种双倍半硼烷倍半萜的便捷对映选择性合成。嗯
• Regioselective Ring‐Opening of Oxetanes Catalyzed by Lewis Superacid Al(C₆F₅)₃
  作者：Marina Bellido、Carlos Riego‐Mejías、Giuseppe Sciortino、Xavier Verdaguer、Agustí Lledós、Antoni Riera

  DOI：10.1002/adsc.202301183

  日期：2024.2.20

  with elements of group 13 (B, Al, Ga, In, Tl) have been used multiple times as canonical LAs.9 One of the most common strategies to fine tune the properties of acids in order to convert them into Lewis superacids is by employing electron-withdrawing substituents (R=EWG). Numerous successful examples can be found in the chemistry of LAs bearing fluorinated aryl substituents, denoted as E(ArF).10, 11 While

  介绍 贵金属在均相催化中表现出出色的功效，为众多全合成做出了重大贡献。1, 2然而，对不依赖昂贵过渡金属的催化转化的需求日益增长。3因此，人们对探索源自第一行和主族丰富金属的催化剂的兴趣与日俱增。路易斯酸（LA）催化展示了该领域不断扩展的前景。4 LA 是可以在其空轨道中接受电子对的分子。5 OLAh 引入的术语“路易斯超强酸”对强于无水 AlCl 3的酸进行了分类。6 Krossing 和同事后来提出定义那些在气相中比单体 SbF 5更强的 LA。7有多种方法可以衡量 LA 的强度。一般来说，它们涉及吸引力（静电、共价、色散）和排斥相互作用的折衷。Greb 最近报道了一项广泛的研究，对一组强 LA 的路易斯超酸性进行了分类。8在这方面，含有第 13 族元素（B、Al、Ga、In、Tl）的化合物 ER 3已多次用作标准 LA。9 微调酸的性质以将其转化为路易斯超强酸的最常见策略之一是使用吸电子取代基