6-(2-methoxyphenyl)-1-hexene | 89789-98-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-(2-methoxyphenyl)-1-hexene
• 英文别名: 1-(hex-5-en-1-yl)-2-methoxybenzene；1-hex-5’-enyl-2-methoxybenzene；1-Hex-5-enyl-2-methoxybenzene
• CAS: 89789-98-0
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: TWNHYTZXFKBBJJ-UHFFFAOYSA-N

物化性质

• 沸点：
  277.3±19.0 °C(Predicted)
• 密度：
  0.917±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-(2-methoxyphenyl)-1-hexene 在 palladium on activated charcoal 氢气 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 异丙醇 为溶剂， 反应 4.0h， 生成 2-Hydroxy-5-[2-[[2-hydroxy-6-(2-methoxyphenyl)hexyl]amino]ethoxy]benzamide
  参考文献：
  名称：

  .beta.-Adrenergic blocking agents: substituted phenylalkanolamines. Effect of side-chain length on .beta.-blocking potency in vitro

  摘要：

  The synthesis of a group of potential beta-blockers bearing a new 5-ethoxysalicylamide substituent on nitrogen is described. These compounds were tested for beta-adrenergic blocking potency in vitro and compared with analogous compounds bearing a tert-butyl group on nitrogen. The new N-substituent increased the beta-blocking potency substantially. In a series of five homologous compounds of the type Ar(CH2)nCHOHCH2NHR (R = 5-ethoxysalicylamide; n = 0-4), two maxima of beta-blocking potency were found for n = 0 and 2. Moreover, the carbon isostere of the corresponding (aryloxy)propanolamine still proved to be a very potent beta-blocker. The ether oxygen in the side chain is therefore not an absolute requirement for activity. Structure-activity relationships are discussed.

  DOI：

  10.1021/jm00373a003
• 作为产物：
  描述：

  2-甲氧基苯甲醇 在 三溴化磷 、 magnesium 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 22.25h， 生成 6-(2-methoxyphenyl)-1-hexene
  参考文献：
  名称：

  链长度对 Aphidocolin/Stemodin 支架的烯烃-芳烃间位光环加成反应中内/外立体选择性的影响

  摘要：

  分子内烯烃-芳烃间位光环加成反应是强大的“无试剂”转化，可从易于获得的起始材料形成复杂的三维稠环系统。通过明智的系链设计与连续流动相结合，证明具有四元系链的底物也可以以良好的产率进行间位光环加成，从而能够获得天然产物骨架。

  DOI：

  10.1002/ejoc.202400463

文献信息

• Process for preparing 1-bromoalkylbenzene derivatives and intermediates thereof
  申请人：SUMITOMO CHEMICAL COMPANY LIMITED

  公开号：EP0637580A1

  公开（公告）日：1995-02-08

  A 1-bromoalkylbenzene derivative is prepared by reacting a phenylalkene derivative with hydrogen bromide in the presence of a non-polar solvent. The phenylalkene derivative is prepared by reacting an alkenyl halide with metal magnesium to form a Grignard reagent, and then reacting the Grignard reagent with a benzyl halide derivative. An allyl Grignard reagent is prepared by reacting continuously an allyl halide derivative with metal magnesium in an organic solvent, in which the allyl halide derivative and metal magnesium are continuously added to the reaction system and the allyl Grignard reagent formed is continuously removed from the reaction system. The processes provide the intended compounds in high yields, high selectivities and high purities.

  1-bromoalkylbenzene derivative is prepared by reacting a phenylalkene derivative with hydrogen bromide in the presence of a non-polar solvent.苯基烷烃衍生物的制备方法是先使烯基卤化物与金属镁反应生成格氏试剂，然后使格氏试剂与苄基卤化物衍生物反应。烯丙基格氏试剂是通过烯丙基卤化物衍生物与金属镁在有机溶剂中连续反应制备的，其中烯丙基卤化物衍生物和金属镁被连续加入反应体系，形成的烯丙基格氏试剂被连续从反应体系中移除。这些工艺可提供高产率、高选择性和高纯度的预期化合物。
• US5637736A
  申请人：——

  公开号：US5637736A

  公开（公告）日：1997-06-10
• US6063940A
  申请人：——

  公开号：US6063940A

  公开（公告）日：2000-05-16
• .beta.-Adrenergic blocking agents: substituted phenylalkanolamines. Effect of side-chain length on .beta.-blocking potency in vitro
  作者：Walter Fuhrer、Franz Ostermayer、Markus Zimmermann、Max Meier、Hedi Mueller

  DOI：10.1021/jm00373a003

  日期：1984.7

  The synthesis of a group of potential beta-blockers bearing a new 5-ethoxysalicylamide substituent on nitrogen is described. These compounds were tested for beta-adrenergic blocking potency in vitro and compared with analogous compounds bearing a tert-butyl group on nitrogen. The new N-substituent increased the beta-blocking potency substantially. In a series of five homologous compounds of the type Ar(CH2)nCHOHCH2NHR (R = 5-ethoxysalicylamide; n = 0-4), two maxima of beta-blocking potency were found for n = 0 and 2. Moreover, the carbon isostere of the corresponding (aryloxy)propanolamine still proved to be a very potent beta-blocker. The ether oxygen in the side chain is therefore not an absolute requirement for activity. Structure-activity relationships are discussed.
• Effect of Tether Length on endo/exo Stereoselectivity in Alkene–Arene meta‐Photocycloaddition Reactions towards the Aphidocolin/Stemodin Scaffolds
  作者：Aljazy A. A. Alshammari、Joseph W. Boyd、Nicola Greaves、Jason G. Kettle、John E. McKendrick、Lewis G. Parker、Andrew T. Russell、Abubakar Sani、Christopher D. Smith

  DOI：10.1002/ejoc.202400463

  日期：——

  Intramolecular alkene-arene meta-photocycloaddition reactions are powerful ‘reagentless’ transformations that form complex three-dimensional fused-ring systems from readily accessible starting materials. By judicious tether design in combination with continuous flow it is demonstrated that substrates with a four-membered tether can also undergo meta-photocycloaddition in good yield, enabling access

  分子内烯烃-芳烃间位光环加成反应是强大的“无试剂”转化，可从易于获得的起始材料形成复杂的三维稠环系统。通过明智的系链设计与连续流动相结合，证明具有四元系链的底物也可以以良好的产率进行间位光环加成，从而能够获得天然产物骨架。