1-氯-2-丙-2-烯氧基苯 | 20788-42-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-氯-2-丙-2-烯氧基苯
• 英文名称: allyl 2-chlorophenyl ether
• 英文别名: 1-(allyloxy)-2-chlorobenzene；allyl o-chlorophenyl ether；1-chloro-2-(prop-2-en-1-yloxy)benzene；1-chloro-2-prop-2-enoxybenzene
• CAS: 20788-42-5
• 化学式: C₉H₉ClO
• mdl: MFCD00018249
• 分子量: 168.623
• InChiKey: NQQZRGSSVFDPLC-UHFFFAOYSA-N

物化性质

• 沸点：
  118-120 °C(Press: 25 Torr)
• 密度：
  1.133 g/cm3(Temp: 15 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2909309090

反应信息

• 作为反应物：
  描述：

  1-氯-2-丙-2-烯氧基苯 在 乙基氯化镁 、 iron(II) chloride 作用下， 以 四氢呋喃 、 间二甲苯 为溶剂， 反应 1.0h， 以96%的产率得到邻氯苯酚
  参考文献：
  名称：

  Highly practical iron-catalyzed C–O cleavage reactions

  摘要：

  在乙基镁氯的存在下，容易用铁催化剂切断各种烯丙基、肉桂基和苄基的C–O键。该方法操作简单（用二甲苯–四氢呋喃，在室温下反应1小时），所需催化剂用量低（1 mol% FeCl2），并且对卤素、酯、胺、醚和烯烃具有耐受性。烯丙基部分转化为挥发性烃，省去了繁琐的产品分离步骤。

  DOI：

  10.1039/c3cy00266g
• 作为产物：
  描述：

  3-Bromoprop-2-enyl 2-chlorophenyl ether 在 samarium diiodide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 3.0h， 以80%的产率得到1-氯-2-丙-2-烯氧基苯
  参考文献：
  名称：

  Cyclizations and Rearrangements of Samarium Diiodide-Generated Vinyl Radicals

  摘要：

  Vinyl bromides 1, 5, 15, 20, 23, 27, 33a,b, 41a-c, 44a-c, 46a,b, 52a,b, 55a, 56a,b, and 60a,b react with samarium diiodide in THF and/or acetonitrile to give the corresponding vinyl radicals. Radicals 3, 7, and 16 afforded products deriving from cyclization on the adjacent triple bond in a 5-(pi-exo)exo, 6-(pi-endo)exo, and 6-(pi-exo)exo mode, respectively. Radical 7 undergoes competitive 1,5-hydrogen translocation. Vinyl radicals 21 and 24 readily cyclize on the proximal double bond, leading to 5- and 6-membered rings, respectively. Thienyl-substituted radical 28 leads to a product deriving from 5-exo cyclization on the thiophene ring and subsequent beta-fission of the C-S bond, whereas thienyl-substituted radicals 34a,b undergo almost exclusively 1,5-hydrogen translocation. Aryl-substituted radicals obtained from vinyl bromides 41, 44, 46, 52, and 55 do not form any products deriving from 5-exo or 6-exo cyclization (or ipso cyclization). Finally, naphthyl-substituted radicals 57a and 61a give only direct reduction products, whereas the radical 61b affords, in addition to the direct reduction product, a rearranged product deriving from a 1,3-radical migration of the naphthylthio group. Evidence is reported for the reduction of EWG-substituted benzene rings and thio-substituted naphthalene rings to radical anions, which can fragment on the side chain with the elimination of allyl radicals. alpha-Oxy(and alpha-thio)-substituted radicals deriving from 1,5-shift rearrange to alcohols (and thiols) through a Wittig rearrangement or a cyclization/fragmentation process.

  DOI：

  10.1021/jo00128a013

文献信息

• Thermodynamic, spectroscopic, and density functional theory studies of allyl aryl and prop-1-enyl aryl ethers. Part 1. Thermodynamic data of isomerization
  作者：Esko Taskinen

  DOI：10.1039/b101837j

  日期：——

  A chemical equilibration study of the relative thermodynamic stabilities of seventy isomeric allyl aryl ethers (a) and (Z)-prop-1-enyl aryl ethers (b) in DMSO solution has been carried out. From the variation of the equilibrium constant with temperature the Gibbs energies, enthalpies, and entropies of isomerization at 298.15 K have been evaluated. Because of their low enthalpies, the (Z)-prop-1-enyl aryl ethers are strongly favored at equilibrium, the Gibbs energies of the a→b isomerization ranging from −12 to −23 kJ mol−1. The entropy contribution is negligible in most reactions, but occasionally small positive values less than +10 J K−1 mol−1 of the entropy of isomerization are found. The equilibration studies were also extended to involve two pairs of related isomeric ethers with a Me substituent on C(2) of the olefinic bond. The Me substituent was found to increase the relative thermodynamic stability of the allylic ethers by ca. 3.4 kJ mol−1.

  通过对70对异构化的烯丙基苯基醚（a）和（Z）-丙-1-烯基苯基醚（b）在DMSO溶液中的化学平衡研究，考察了它们相对热力学稳定性的变化。从平衡常数随温度的变化中，评估了在298.15 K下的异构化吉布斯自由能、焓和熵。由于其低焓值，（Z）-丙-1-烯基苯基醚在平衡状态下具有显著优势，a→b异构化的吉布斯自由能范围从-12至-23 kJ/mol。在大多数反应中，熵的贡献可以忽略不计，但偶尔会发现小于+10 J/K·mol的正值。平衡研究还扩展到涉及两对在烯键C(2)位置带有甲基取代基的相关异构化醚。甲基取代基可以增加烯丙基醚的相对热力学稳定性约3.4 kJ/mol。
• Direct access to β-seleno sulfones at room temperature through selenosulfonylation of alkenes
  作者：Kai Sun、Yunhe Lv、Zuodong Shi、Fangfang Fu、Chong Zhang、Zhiguo Zhang

  DOI：10.1007/s11426-016-0412-0

  日期：2017.6

  by the direct selenosulfonylation of alkenes. This protocol is operationally simplistic, has a wide substrate scope, uses readily available seleno and sulfonyl sources, and is amenable to gram-scale synthesis. This reaction represents a significant addition to the limited number of reactions available for the intermolecular selenide difunctionalization of alkenes and would be useful for the synthesis

  已经开发了一种新的协议，用于通过烯烃的直接磺磺酰基化形成C-Se和C-S键。该协议操作简单，具有广泛的底物范围，使用易于获得的硒代和磺酰基源，并且适用于克级合成。该反应是对烯烃分子间亚硒酸酯双官能化可用反应数量有限的重要补充，可用于合成含硫和硒的分子
• Subsupercritical Water Generated by Inductive Heating Inside Flow Reactors Facilitates the Claisen Rearrangement
  作者：Andreas Kirschning、Mona Oltmanns

  DOI：10.1055/s-0040-1705945

  日期：2020.12

  O-allylated phenols, including fluorine-modified phenols, is facilitated in aqueous media at high temperatures and pressures under flow conditions, as opposed to organic solvents. The O-allylation of phenols can be coupled with the Claisen rearrangement in an integrated flow system. Publication History Received: 14 August 2020 Accepted after revision: 16 September 2020 Publication Date: 27 October 2020

  摘要 与有机溶剂相反，在水性介质中，高温和高压下，流动条件下，缺电子的O-烯丙基化酚（包括氟改性的酚）的Claisen重排容易进行。苯酚的O-烯丙基化可以与集成流系统中的Claisen重排结合。 出版历史 收到：2020年8月14日 修订后接受：2020年9月16日 发布日期： 2020年10月27日（在线） ©2020年。Thieme。版权所有 Georg Thieme Verlag KGRüdigerstraße14，70469斯图加特，德国
• Photo-induced Carboiodination: A Simple Way to Synthesize Functionalized Dihydrobenzofurans and Indolines
  作者：Xiaobo Yang、Wenbo Liu、Lu Li、Wei Wei、Chao-Jun Li

  DOI：10.1002/chem.201603608

  日期：2016.10.17

  readily available and cheap aryl bromides and sodium iodide as the starting materials to synthesize valuable functionalized dihydrobenzofurans and indolines in good to excellent yields with broad functional‐group compatibility. As examples to demonstrate the utility of this protocol, gram‐scale reactions and further transformations of the products were accomplished towards the synthesis of bioactive

  在此，我们报告了在非常温和的条件下发生的简单的氧化还原中性和pH中性光诱导的碳碘化反应。该方案采用容易获得且便宜的芳基溴化物和碘化钠作为起始原料，以良好的产率和优异的产率以及广泛的官能团相容性来合成有价值的官能化二氢苯并呋喃和二氢吲哚。作为证明该方案实用性的实例，完成了克级反应和产物的进一步转化，以合成生物活性药物候选物。最重要的是，据我们所知，该反应是级联原子-自由基转移加成反应的第一个例子，涉及芳族C-Br键的裂解。
• Peroxodisulfate-mediated selenoamination of alkenes yielding amidoselenide-containing sulfamides and azoles
  作者：Kai Sun、Xin Wang、Yunhe Lv、Gang Li、Hezhen Jiao、Changwei Dai、Yangyang Li、Chong Zhang、Lin Liu

  DOI：10.1039/c6cc04225b

  日期：——

  A novel intermolecular selenoamination of alkenes has been successfully developed and a series of structurally diverse vicinal amidoselenides were effectively obtained under mild heating.

  一种新型的烯烃间分子硒氨基化反应已成功开发，并在温和加热下有效地获得了一系列结构多样的邻氨基硒化物。