allyl-(2-bromo-cyclohexyl)-ether | 29840-04-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: allyl-(2-bromo-cyclohexyl)-ether
• 英文别名: 2-Brom-1-allyloxy-cyclohexan；Allyl-(2-brom-cyclohexyl)-aether；1-Bromo-2-prop-2-enoxycyclohexane
• CAS: 29840-04-8
• 化学式: C₉H₁₅BrO
• 分子量: 219.121
• InChiKey: VYUSRVIPKBSEJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  allyl-(2-bromo-cyclohexyl)-ether 在 吡啶 、 chromium(III) oxide 、 bis(dimethylglyoximato)pyridinecobaltate(I) ion 、 magnesium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 6.0h， 生成 cis-3-methylenehexahydrobenzofuran-2-one
  参考文献：
  名称：

  双(二甲基乙醛肟)(吡啶)钴(I)、钴肟(I)与2-(烯丙氧基)乙基卤化物的反应和所得有机钴肟的光解

  摘要：

  2-（烯丙氧基）乙基卤化物与钴肟（I）的反应通过从钴肟（I）到卤化物的电子转移产生（四氢-3-呋喃基）甲基钴肟以产生自由基阴离子。卤化物离子断裂产生有机自由基和闭环产生(四氢-3-呋喃基)甲基自由基，随后有机自由基与钴肟(II)之间的自由基偶联。有机钴肟的结构是通过在有氧或无氧条件下对光解产物的分析来确定的。

  DOI：

  10.1246/bcsj.55.1498
• 作为产物：
  描述：

  2-(allyloxy)cyclohexyl tosylate 在 1,2-二溴乙烷 、 magnesium bromide 作用下， 以 乙醚 为溶剂， 以60%的产率得到allyl-(2-bromo-cyclohexyl)-ether
  参考文献：
  名称：

  双(二甲基乙醛肟)(吡啶)钴(I)、钴肟(I)与2-(烯丙氧基)乙基卤化物的反应和所得有机钴肟的光解

  摘要：

  2-（烯丙氧基）乙基卤化物与钴肟（I）的反应通过从钴肟（I）到卤化物的电子转移产生（四氢-3-呋喃基）甲基钴肟以产生自由基阴离子。卤化物离子断裂产生有机自由基和闭环产生(四氢-3-呋喃基)甲基自由基，随后有机自由基与钴肟(II)之间的自由基偶联。有机钴肟的结构是通过在有氧或无氧条件下对光解产物的分析来确定的。

  DOI：

  10.1246/bcsj.55.1498

文献信息

• A new synthetic route to alkenyl-substituted tetrahydrofurans via successive intra- and inter-molecular radical reactions
  作者：Osamu Moriya、Masato Kakihana、Yoshikiyo Urata、Toshio Sugizaki、Toshifumi Kageyama、Yoshio Ueno、Takeshi Endo

  DOI：10.1039/c39850001401

  日期：——

  Tetrahydrofurans with alkenyl substituents were obtained by the radical cyclization of β-bromoethers using allyltri-n-butylstannane in a one-pot reaction.

  具有烯基取代基的四氢​​呋喃是通过烯丙基三正丁基锡烷在一锅反应中对β-溴醚进行自由基环化而获得的。
• Bresson,A. et al., Bulletin de la Societe Chimique de France, 1970, p. 2432 - 2439
  作者：Bresson,A. et al.

  DOI：——

  日期：——
• Schmidt; Bartholome; Luebke, Chemische Berichte, 1922, vol. 55, p. 2103
  作者：Schmidt、Bartholome、Luebke

  DOI：——

  日期：——
• Generation and Mesolysis of PhSeSiR₃]^•-:  Mechanistic Studies by Laser Flash Photolysis and Application for Bimolecular Group Transfer Radical Reactions
  作者：Ganesh Pandey、K. S. Sesha Poleswara Rao、D. K. Palit、J. P. Mittal

  DOI：10.1021/jo972345e

  日期：1998.6.1

  The investigation presented in this paper explores the mechanistic aspects and synthetic potentials of PET promoted reductive activation of selenosilane la to its radical anion la(-.). PET activation of la is achieved through a photosystem comprising a light-absorbing electron-rich aromatic (ERA), such as DMN or DMA, as an electron donor and ascorbic acid as a co-oxidant. The evidence for the ET from excited singlet states of DMN as well as DMA to la is suggested by estimating negative Delta G(et) (-51 and -43.46 kcal mol(-1), respectively) values and nearly diffusion-controlled fluorescence quenching rate constants (k(q)TR) 0.36 x 10(10) M-1 s(-1) and 0.28 x 10(10) M-1 s(-1), respectively, from time-resolved fluorescence quenching study. The transient absorption spectra of DMN.+, DMA(.+), and la(.-) are obtained initially by pulse radiolysis in order to correlate the time-resolved absorption spectral data. Laser flash photolysis studies in the nanosecond time domain have confirmed the generation of la(.-), DMN.+, and DMA(.+), supporting the participation of the triplet state of DMN or DMA in the ET reaction. Mesolytic cleavage of 1a(.-) produced a silyl radical and a phenyl selenide anion. The preparative PET activation of la in acetonitrile in the presence of DMN or DMA leads to the formation of 5 and 6, confirming the fragmentation pattern of la(.-). The overall ET rate constants (K-r(DMN) = 0.99 x 10(10) M-1 s(-1) and k(r)(DMA) = 1.62 x 10(10) M-1 s(-1)) and limiting quantum yields (phi(lim)DMN) = 0.034 and phi(lim)(DMA) = 0.12) are estimated from the inverse plot (1/[la] vs 1/phi(dis)) Obtained by measuring the dependence of photodissociation quantum yields of la at its maximum concentration in the presence of DMN or DMA. Silicon-centered radical species generated from the mesolysis of la(.-) are utilized for initiating a radical reaction by the abstraction of halogen atom from -C-X (X = Cl, Br) bonds, while PhSe- terminates the radical sequences via PhSeSePh. This concept is successfully applied for the bimolecular group transfer (BMGT) radical reactions and intermolecular radical chain addition reactions.
• Schmidt,E.; Bartholome; Luebke, Chemische Berichte, 1922, vol. 55, p. 2106
  作者：Schmidt,E.、Bartholome、Luebke

  DOI：——

  日期：——