1-异丙烯基-2,5-二甲氧基-4-甲基苯 | 39701-09-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-异丙烯基-2,5-二甲氧基-4-甲基苯
• 英文名称: Δ8,9-dehydro-4-hydroxythymol dimethyl ether
• 英文别名: Styrene, 2,5-dimethoxy-alpha,4-dimethyl-；1,4-dimethoxy-2-methyl-5-prop-1-en-2-ylbenzene
• CAS: 39701-09-2
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: BKYVJXZONZSTIB-UHFFFAOYSA-N

物化性质

• 保留指数：
  1443.4

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  1-异丙烯基-2,5-二甲氧基-4-甲基苯 在 吡啶 、 甲醇 、 Porcine pancreas lipase type II 、 dimethyl sulfide borane 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲基叔丁基醚 、 二甲基亚砜 为溶剂， 反应 10.0h， 生成 (3R)-3-(2,5-dimethoxy-4-methylphenyl)butanenitrile
  参考文献：
  名称：

  Lipase-mediated resolution of substituted 2-aryl-propanols: application to the enantioselective synthesis of phenolic sesquiterpenes

  摘要：

  A comprehensive study of the lipase-mediated resolution of substituted 2-aryl-propanols is reported. The latter alcohols were submitted to the irreversible acetylation catalyzed either by PPL, CRL, or lipase PS. The enantioselectivity of these transformations was dependent on the type of lipase used. The type of substituents and particularly their position on the aromatic ring strongly affected the selectivity of the reaction. The experiments described prove that PPL is the more versatile lipase catalyzing the acetylation with an enantiomeric ratio (E) value that ranges from 1 up to 144, depending on the substrate used. Conversely, the same transformations were catalyzed by CRL and lipase PS with an enantiomeric ratio value, which is always less than 5. The remarkable behavior of PPL was exploited in the large scale resolution of some substituted 2-aryl-propanols whose enantiomeric forms are relevant building blocks in the enantioselective synthesis of phenolic sesquiterpenes. By these means, the synthesis of (S)-turmeronol B and the formal syntheses of (R)-curcumene, (R)-curcuphenol, (R)-xanthorrhizol, and (R)-curcuhydroquinone were accomplished. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.03.012
• 作为产物：
  描述：

  2,5-二甲氧基甲苯 在 potassium tert-butylate 、 四氯化锡 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-异丙烯基-2,5-二甲氧基-4-甲基苯
  参考文献：
  名称：

  在酸催化下通过高区域选择性环氧化物打开合成环戊烯型倍半萜的方法

  摘要：

  摘要获得铜烯型倍半萜烯是一项重大的合成挑战，这主要是由于立体位阻四元中心的构建。我们在本文中报道了通过路易斯酸催化的丙酮甲硅烷基烯醇醚的（+/-）-2，5-二甲氧基-4-甲基-α-甲基苯乙烯氧化物的高度区域选择性开放来成功构建此类季基部分。另外，通过对二环氧乙烷促进的环氧化方案的修饰，实现了高度活化的2，5-二甲氧基-4-甲基-α-苯乙烯的有效环氧化。对这两个关键步骤的密集优化使所需支链高醛缩醛加合物的合成成为了针对烯醇单蛋白的短合成替代品的关键中间体。 图形概要

  DOI：

  10.1007/s00706-018-2199-6

文献信息

• SCHULTE; REISCH; RUCKER, Archiv der Pharmazie, 1963, vol. 296, p. 273 - 281
  作者：SCHULTE、REISCH、RUCKER

  DOI：——

  日期：——
• Asymmetric syntheses of heliannuols B and D
  作者：Jiyong Zhang、Xiaolei Wang、Wenkuan Wang、Weiguo Quan、Xuegong She、Xinfu Pan

  DOI：10.1016/j.tet.2007.05.034

  日期：2007.7

  The synthesis of heliannuol D along with the first synthesis of heliannuol B has been achieved using Mitsunobu reaction and ring-closing metathesis as the key steps. (C) Elsevier Ltd. All rights reserved.
• Sudalai, A.; Rao, G. S. Krishna, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 1-11, p. 520 - 521
  作者：Sudalai, A.、Rao, G. S. Krishna

  DOI：——

  日期：——
• SUDALAI, A.;RAO, G. S. KRISHNA, INDIAN J. CHEM. B, 28,(1989) N, C. 520-521
  作者：SUDALAI, A.、RAO, G. S. KRISHNA

  DOI：——

  日期：——
• Lipase-mediated resolution of substituted 2-aryl-propanols: application to the enantioselective synthesis of phenolic sesquiterpenes
  作者：Stefano Serra

  DOI：10.1016/j.tetasy.2011.03.012

  日期：2011.3

  A comprehensive study of the lipase-mediated resolution of substituted 2-aryl-propanols is reported. The latter alcohols were submitted to the irreversible acetylation catalyzed either by PPL, CRL, or lipase PS. The enantioselectivity of these transformations was dependent on the type of lipase used. The type of substituents and particularly their position on the aromatic ring strongly affected the selectivity of the reaction. The experiments described prove that PPL is the more versatile lipase catalyzing the acetylation with an enantiomeric ratio (E) value that ranges from 1 up to 144, depending on the substrate used. Conversely, the same transformations were catalyzed by CRL and lipase PS with an enantiomeric ratio value, which is always less than 5. The remarkable behavior of PPL was exploited in the large scale resolution of some substituted 2-aryl-propanols whose enantiomeric forms are relevant building blocks in the enantioselective synthesis of phenolic sesquiterpenes. By these means, the synthesis of (S)-turmeronol B and the formal syntheses of (R)-curcumene, (R)-curcuphenol, (R)-xanthorrhizol, and (R)-curcuhydroquinone were accomplished. (C) 2011 Elsevier Ltd. All rights reserved.