2'-bromophenyl cyclohex-1-enylmethyl ether | 149171-96-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2'-bromophenyl cyclohex-1-enylmethyl ether
• 英文别名: 1-Bromo-2-(cyclohexen-1-ylmethoxy)benzene
• CAS: 149171-96-0
• 化学式: C₁₃H₁₅BrO
• 分子量: 267.166
• InChiKey: FVAGFCVETGVGQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  3
• 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：

  2'-bromophenyl cyclohex-1-enylmethyl ether 在 oxonium 、 叔丁基锂 、 lithium bromide 作用下， 反应 6.0h， 生成 1-(2-hydroxybenzyl)cyclohexene
  参考文献：
  名称：

  Regio- and stereoselective copper-induced isomerization of 2-alkenyl 2-lithiophenyl ethers to 2-(2-alkenyl)phenols

  摘要：

  N-Allyl-N-(2-lithioallyl)aniline undergoes intramolecular carbometallation via 5-exo addition on treatment with CuCN. 2-Alkenyl 2-bromophenyl ethers rearrange to 2-(2-alkenyl)phenols by bromine-lithium exchange and further transmetallation with CuCN. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01379-8
• 作为产物：
  描述：

  3-甲氧基环己烯 在 三溴化磷 、 potassium carbonate 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 2'-bromophenyl cyclohex-1-enylmethyl ether
  参考文献：
  名称：

  1,3,2-二氮杂磷烯催化的有机卤化物还原环化**

  摘要：

  1,3,2-二氮杂磷烯氢化物 (DAP-H) 被证明是可见光照射下芳基卤化物和烷基卤化物还原自由基环化的有效催化剂。关键的 DAP 催化剂周转是通过 DBU 辅助形成的 DAP 卤化物和 HBpin 之间的σ键复分解实现的。

  DOI：

  10.1002/anie.202202306

文献信息

• Synthetic approaches toward spiro[2,3-dihydro-4H-1-benzopyran-4,1'-cyclohexan]-2-one derivatives via radical reactions: total synthesis of (.+-.)-lycoramine
  作者：Miyuki Ishizaki、Kunihiko Ozaki、Akira Kanematsu、Takeshi Isoda、Osamu Hoshino

  DOI：10.1021/jo00067a019

  日期：1993.7

  Syntheses of spiro[2,3-dihydro-4H-1-benzopyran-4,1'-cyclohexan]-2-one derivatives by reaction sequences including a radical reaction and a total synthesis of (+/-)-lycoramine (2) are described. Radical reactions (Bu3SnH,AIBN) of 1-[(1'-cyclohexenylmethyl)oxy]-2-halobenzenes 23b-d in boiling benzene gave the corresponding spiro[2,3-dihydrobenzofuran-3,1'-cyclohexanes] 26a,b in good yields, whereas the reaction of 1-(1'-cyclohexenylethoxy)-2-bromobenzene (25) under similar conditions afforded a mixture of spiro[2,3-dihydro-4H-1-benzopyran-4,1'-cyclohexane] 27 and benzoxepin 28. Furthermore, the radical reaction of ethyl 2-[(2'-bromoaryl)oxy]-1-cyclohexenylacetate 37a produced ethyl 2-spiro[2,3-dihydrobenzofuran-3,1'-cyclohexane]carboxylate 38 in good yield. Compound 38 was converted to spiro[2,3-dihydro-4H-1-benzopyran-4,1'-cyclohexane]-2,4'-dione 40 by treatment With SmI2 and then with 3 N HCl. Spiro[2,3-dihydro-4H-1-benzopyran-4,1'-cyclohexane]-2,4'-dione 40 was transformed to (+/-)-lycoramine (2) in four steps and 43% overall yield.
• Regio- and stereoselective copper-induced isomerization of 2-alkenyl 2-lithiophenyl ethers to 2-(2-alkenyl)phenols
  作者：José Barluenga、Roberto Sanz、Francisco J. Fañanás

  DOI：10.1016/s0040-4039(97)01379-8

  日期：1997.8

  N-Allyl-N-(2-lithioallyl)aniline undergoes intramolecular carbometallation via 5-exo addition on treatment with CuCN. 2-Alkenyl 2-bromophenyl ethers rearrange to 2-(2-alkenyl)phenols by bromine-lithium exchange and further transmetallation with CuCN. (C) 1997 Elsevier Science Ltd.
• 1,3,2‐Diazaphospholene‐Catalyzed Reductive Cyclizations of Organohalides**
  作者：Johannes Klett、Łukasz Woźniak、Nicolai Cramer

  DOI：10.1002/anie.202202306

  日期：2022.7.25

  1,3,2-diazaphospholenes hydrides (DAP-H) are shown as efficient catalysts for reductive radical cyclization of aryl and alkyl halides under irradiation with visible light. The pivotal DAP catalyst turnover was achieved by a DBU-assisted σ-bond metathesis between the formed DAP halide and HBpin.

  1,3,2-二氮杂磷烯氢化物 (DAP-H) 被证明是可见光照射下芳基卤化物和烷基卤化物还原自由基环化的有效催化剂。关键的 DAP 催化剂周转是通过 DBU 辅助形成的 DAP 卤化物和 HBpin 之间的σ键复分解实现的。