1,4-dimethoxy-2-methyl-5-[(2R)-1-phenylsulfanylpropan-2-yl]benzene | 289507-50-2

• 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: 1,4-dimethoxy-2-methyl-5-[(2R)-1-phenylsulfanylpropan-2-yl]benzene
• CAS: 289507-50-2
• 化学式: C₁₈H₂₂O₂S
• 分子量: 302.437
• InChiKey: WZCVXOJCHRYOME-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4-dimethoxy-2-methyl-5-[(2R)-1-phenylsulfanylpropan-2-yl]benzene 在 manganese(IV) oxide 、 ammonium molybdate 、 正丁基锂 、 ammonium cerium (IV) nitrate 、 双氧水 、 tetra-n-butylammoniumfluoride trihydrate 、 二乙胺 、 naphthalen-1-yl-lithium 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 16.67h， 生成 (S,E)-2-methyl-6-(4-methyl-3,6-dioxocyclohexa-1,4-dienyl)hept-2-enal
  参考文献：
  名称：

  Preparation and use of enantioenriched 2-aryl-propylsulfonylbenzene derivatives as valuable building blocks for the enantioselective synthesis of bisabolane sesquiterpenes

  摘要：

  We have demonstrated that different enantioenriched 2-arylpropylsufonylbenzene derivatives are very useful building blocks for the synthesis of aromatic bisabolane sesquiterpenes. Their preparation and the exploitation of their chemical reactivity have been comprehensively investigated. Accordingly, the naturally occurring bisabolane sesquiterpenes (-)-curcuphenol, (-)-xanthorrhizol, (+)-glandulone A, (+)-curcudiol, (+)-turmerone and (+)-curcudiol-10-one were synthesized in high enantiomeric purity. It is worth noting that the compounds (+)-curcudiol-10-one and (+)-glandulone A were prepared in enantioenriched form for the first time. Through the proposed synthetic approaches, we were able to confirm both chemical structures and the absolute configurations previously assigned to the two aforementioned sesquiterpenes. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.10.016
• 作为产物：
  描述：

  (S)-2-(2,5-dimethoxy-4-methylphenyl)-3-hydroxypropyl acetate 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 三丁基膦 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 生成 1,4-dimethoxy-2-methyl-5-[(2R)-1-phenylsulfanylpropan-2-yl]benzene
  参考文献：
  名称：

  Enantioselective total synthesis of heliannuols D and A †

  摘要：

  Heliannuols D和A表现出拮抗作用，首次通过碱介导的分子内环化合成，它们是通过苯酚环氧化物的手性选择性合成的，绝对结构通过全合成确立。

  DOI：

  10.1039/b003553j

文献信息

• Enantioselective total synthesis of heliannuols D and A †
  作者：Kenya Takabatake、Izumi Nishi、Mitsuru Shindo、Kozo Shishido

  DOI：10.1039/b003553j

  日期：——

  Heliannuols D and A, which exhibit allelopathic activity, were synthesized enantioselectively via a base-mediated intramolecular cyclisation of a phenolic epoxide for the first time, and the absolute structures were established by total synthesis.

  Heliannuols D和A表现出拮抗作用，首次通过碱介导的分子内环化合成，它们是通过苯酚环氧化物的手性选择性合成的，绝对结构通过全合成确立。
• Preparation and use of enantioenriched 2-aryl-propylsulfonylbenzene derivatives as valuable building blocks for the enantioselective synthesis of bisabolane sesquiterpenes
  作者：Stefano Serra

  DOI：10.1016/j.tetasy.2014.10.016

  日期：2014.12

  We have demonstrated that different enantioenriched 2-arylpropylsufonylbenzene derivatives are very useful building blocks for the synthesis of aromatic bisabolane sesquiterpenes. Their preparation and the exploitation of their chemical reactivity have been comprehensively investigated. Accordingly, the naturally occurring bisabolane sesquiterpenes (-)-curcuphenol, (-)-xanthorrhizol, (+)-glandulone A, (+)-curcudiol, (+)-turmerone and (+)-curcudiol-10-one were synthesized in high enantiomeric purity. It is worth noting that the compounds (+)-curcudiol-10-one and (+)-glandulone A were prepared in enantioenriched form for the first time. Through the proposed synthetic approaches, we were able to confirm both chemical structures and the absolute configurations previously assigned to the two aforementioned sesquiterpenes. (C) 2014 Elsevier Ltd. All rights reserved.