1-(环己烯-1-基)-2-甲氧基苯 | 22618-48-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-(环己烯-1-基)-2-甲氧基苯
• 英文名称: 1-cyclohexenyl-2-methoxybenzene
• 英文别名: 1-(Cyclohex-1-en-1-yl)-2-methoxybenzene；1-(cyclohexen-1-yl)-2-methoxybenzene
• CAS: 22618-48-0
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: QDEHJTCYJGEWND-UHFFFAOYSA-N

物化性质

• 熔点：
  17.1 °C
• 沸点：
  105-110 °C(Press: 0.8 Torr)
• 密度：
  1.012±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• 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：

  1-(环己烯-1-基)-2-甲氧基苯 在 eosin 作用下， 以 乙腈 为溶剂， 反应 2.33h， 以93%的产率得到3-(2-methoxyphenyl)cyclohex-2-enone
  参考文献：
  名称：

  Visible Light Promoted Allylic C–H Oxidation

  摘要：

  A mild and efficient one-pot visible light-induced method has been developed for the allylic oxidation. The oxidation of allylic systems has played a prominent role in this context as possibly the most widely applied C-H functionalization, owing to the utility of enones. The allylic C-H oxidation is relatively simple and predictable, even on a preparative scale, because active species generated at the allylic position are stabilized by the double bond.

  DOI：

  10.5562/cca3126
• 作为产物：
  描述：

  邻甲氧基苯甲酸 在 copper(l) iodide 、 1,10-菲罗啉 、 三(1-萘基)膦 、 potassium tert-butylate 、 palladium(II) bromide 作用下， 以 N-甲基吡咯烷酮 、 乙醇 、 均三甲苯 为溶剂， 反应 19.0h， 生成 1-(环己烯-1-基)-2-甲氧基苯
  参考文献：
  名称：

  Arylalkene Synthesis via Decarboxylative Cross-Coupling of Alkenyl Halides

  摘要：

  A bimetallic catalyst system generated from readily available palladium(II) and copper(I) salts, 1,10-phenanthroline and tri-1-naphthylphosphine was found to efficiently mediate the decarboxylative cross-coupling of alkenyl bromides and chlorides with aromatic carboxylates. It allows the regiospecific synthesis of a broad range of aryl- and heteroarylalkenes in high yields.

  DOI：

  10.1021/ol500876x

文献信息

• Nickel-catalyzed cross-couplings of cyclohexenyl phosphate and arylboronic acids
  作者：Yang Nan、Zhen Yang

  DOI：10.1016/s0040-4039(99)00517-1

  日期：1999.4

  The Nickel-catalyzed cross-coupling reaction of cyclohexenylphosphate with a variety of arylboronic acids is described here for the first time. This methodology opens the door to other palladium or nickel-catalyzed coupling reactions involving vinyl phosphates.

  本文首次描述了环己烯基磷酸酯与各种芳基硼酸的镍催化交叉偶联反应。这种方法为其他涉及磷酸乙烯基酯的钯或镍催化的偶联反应打开了大门。
• Well-Defined Air-Stable Palladium HASPO Complexes for Efficient Kumada-Corriu Cross-Couplings of (Hetero)Aryl or Alkenyl Tosylates
  作者：Lutz Ackermann、Anant R. Kapdi、Sabine Fenner、Christoph Kornhaaß、Carola Schulzke

  DOI：10.1002/chem.201002386

  日期：2011.3.1

  Palladium complexes of representative heteroatom‐substituted secondary phosphine oxide (HASPO) preligands were synthesized and fully characterized, including X‐ray crystal structure analysis. Importantly, these well‐defined complexes served as highly efficient catalysts for Kumada–Corriu cross‐coupling reactions of aryl, alkenyl, and even heteroaryl tosylates. Particularly, an air‐stable catalyst derived

  代表的钯络合物ħ etero一汤姆取代小号econdary p hoSPhine ø西德（HASPO）preligands合成并充分表征，包括X射线晶体结构分析。重要的是，这些定义明确的络合物可作为Kumada-Corriu芳基，烯基乃至杂芳基甲苯磺酸酯交叉偶联反应的高效催化剂。特别是，由廉价的PinP（O）H衍生的空气稳定型催化剂显示出极高的催化效力，这导致在极低的反应条件下，在足够宽泛的反应条件下，低催化剂负载下的交叉偶联。
• Enantiopure <i>cis</i> - and <i>trans</i> -2-(2-Aminocyclohexyl)phenols: Effective Preparation, Solid-State Characterization, and Application in Asymmetric Organocatalysis
  作者：Mustafa A. Tezeren、Tolga A. Yeşil、Yunus Zorlu、Tahir Tilki、Erkan Ertürk

  DOI：10.1002/ejoc.201801445

  日期：2018.12.31

  Effective preparation of enantiopure cis‐ and trans‐2‐(2‐aminocyclohexyl)phenols, novel 1,4‐aminoalkylphenols, as well as their performance as chiral organocatalyst are presented.

  介绍了有效制备对映体纯的顺式和反式-2-（2-氨基环己基）苯酚，新型1,4-氨基烷基苯酚及其作为手性有机催化剂的性能。
• Some 1-arylcyclohexane-1,2-diols
  作者：M.T. Davies、D.F. Dobson、D.F. Hayman、G.B. Jackman、M.G. Lester、V. Petrow、O. Stephenson、A.A. Webb

  DOI：10.1016/s0040-4020(01)92725-5

  日期：1962.1

  Only cis-1,2-glycols have been obtained by hydroxylation of some 1-arylcyclohex-1-enes. The configuration of these products has been confirmed by infra-red studies.

  通过一些1-芳基环己-1-烯的羟基化仅获得了顺式-1,2-二醇。这些产品的配置已通过红外研究得到证实。
• Chloropalladation of 1-aryl-ω-methylenebicyclo[n.1.0]alkanes
  作者：William A. Donaldson、Jeffrey T. North、James A. Gruetzmacher、Michael Finley、Daniel J. Stepuazek

  DOI：10.1016/s0040-4020(01)82007-x

  日期：1990.1

  The chloropalladation of 1-aryl-ω-methylenebicyclo[n.l.0]alkanes affords a mixture of (1-aryl-3-chloro-2-methylenecycloalkyl) - and (3-aryl-3-chloro-2-methylenecycloalkyl)palladium chloride dimers in excellent yield. These products have been characterized by 1H NMR spectroscopy. The regioselectivity of the chloropalladation appears to be dependent on ring strain, steric hinderance and to some extent

  1-芳基-ω-亚甲基双环[nl0]烷烃的氯化钯制得（1-芳基-3-氯-2-亚甲基环烷基）-和（3-芳基-3-氯-2-亚甲基环烷基）氯化钯二聚体的混合物。优良的产量。这些产物已经通过1 H NMR光谱表征。氯palpalation的区域选择性似乎取决于环应变，空间位阻，并在某种程度上取决于芳基取代基稳定部分正电荷的能力。