2-methallyloxybenzoyl chloride | 121767-60-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methallyloxybenzoyl chloride
• 英文别名: 2-(2-Methylprop-2-enoxy)benzoyl chloride
• CAS: 121767-60-0
• 化学式: C₁₁H₁₁ClO₂
• 分子量: 210.66
• InChiKey: NUCVDBSDXAVFIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methallyloxybenzoyl chloride 在 4-二甲氨基吡啶 、 碳酸氢钠 、 potassium carbonate 、 N,N-二甲基甲酰胺 、 三氟乙酸 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 3-[(4-hydroxy-2,2,6,6-tetramethyl-1-piperidinyloxy)methyl]-3-methylchroman-4-one
  参考文献：
  名称：

  酰基肼作为酰基自由基的前体

  摘要：

  探索了使用酰基肼（酰肼）作为化学计量产生酰基自由基的前体。检查了两类底物：未取代的酰基肼和被离去基团（2-硝基苯磺酰基或“ nosyl”）取代的酰基肼。两种类型均成功转化为酰基自由基，然后被氮氧自由基捕获，得到了酰氧基胺产物。对两种类型的底物都证明了环化反应。还开发了McFayden-Stevens反应的低温修饰方法。

  DOI：

  10.1016/s0040-4020(02)00490-8
• 作为产物：
  描述：

  2-[(2-甲基-2-丙烯-1-基)氧基]苯甲酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 2-methallyloxybenzoyl chloride
  参考文献：
  名称：

  酰基肼作为酰基自由基的前体

  摘要：

  探索了使用酰基肼（酰肼）作为化学计量产生酰基自由基的前体。检查了两类底物：未取代的酰基肼和被离去基团（2-硝基苯磺酰基或“ nosyl”）取代的酰基肼。两种类型均成功转化为酰基自由基，然后被氮氧自由基捕获，得到了酰氧基胺产物。对两种类型的底物都证明了环化反应。还开发了McFayden-Stevens反应的低温修饰方法。

  DOI：

  10.1016/s0040-4020(02)00490-8

文献信息

• The free radical chemistry of acyl tellurides: Mechanistic studies and synthetic applications
  作者：Chen Chen、David Crich

  DOI：10.1016/0040-4039(93)85002-e

  日期：1993.3

  Photolysis of acyl aryl tellurides in the presence of thiophenol results in the clean formation of aldehydes indicating homolytic cleavage of the acyl-Te bond and the involvement of acyl radicals. Further cyclization reactions of unsaturated acyltellurides are reported together with some chemistry of the cyclization products.

  在硫酚存在下，酰基芳基碲化物的光解导致醛的干净形成，表明酰基-Te键的均质裂解和酰基自由基的参与。报道了不饱和酰基碲化物的进一步环化反应以及环化产物的一些化学反应。
• Double cyclization of allyloxybenzoic acid chlorides mediated by samarium diiodide giving cyclopropanols
  作者：Mitsuru Sasaki、Jacqueline Collin、Henri B. Kagan

  DOI：10.1016/s0040-4039(00)82276-5

  日期：——

  Cyclopropanols were easily obtained by an unusual double cyclization of 2-allyloxybenzoic acid chlorides mediated by samarium diiodide in THF. A tentative mechanism is discussed.

  环丙醇很容易通过二碘化sa在THF中介导的2-烯丙氧基苯甲酰氯的异常双环化而轻松获得。讨论了一种试探机制。
• Generation and Cyclization of Acyl Radicals from Thiol Esters Under Nonreducing, Tin-Free Conditions
  作者：David Crich、Xiaolin Hao

  DOI：10.1021/jo970500j

  日期：1997.8.1

  The preparation of 2-(2-((tert-butyloxycarbonyl)amino)phenyl)ethyl mercaptan from 2-(2-amino-phenyl)ethanol is described. This thiol is condensed with a series of suitably unsaturated carboxylic acids to give a series of thiol esters. The Boc group is removed and the amine reacted with isoamyl nitrite to give a series of diazonium salts. Exposure to iodide in acetone solution then generates the aryl radical, which undergoes intramolecular homolytic substitution at sulfur with liberation of the acylradical. Following acyl radical cyclization, quenching by iodine and then elimination of HI leads to the isolation of alpha-methylene cycloalkanones in good yield.
• Photoinduced Free Radical Chemistry of the Acyl Tellurides: Generation, Inter- and Intramolecular Trapping, and ESR Spectroscopic Identification of Acyl Radicals
  作者：David Crich、Chen Chen、Jae-Taeg Hwang、Hongwei Yuan、Aristotle Papadatos、Robert I. Walter

  DOI：10.1021/ja00099a011

  日期：1994.10

  Acyl tellurides are prepared in good to excellent yield by the reaction of sodium aryl tellurides with acyl chlorides, or mixed anhydrides, and are found to be moderately air-stable substances. In contrast to previous literature reports, acyl tellurides of aryl and vinyl carboxylic acids are found to be excellent sources of acyl radicals on photolysis with a simple white light source. The acyl radicals so generated may be trapped intermolecularly by dichalcogenides, or by TEMPO in excellent yield. Trapping by N-tert-butyl-alpha-phenyl nitrone produces a stable nitroxide radical which has been characterized by ESR spectroscopy. The very efficient trapping of acyl radicals by acyl tellurides themselves is demonstrated by a crossover experiment. Acyl tellurides are shown to participate in very efficient radical cyclization reactions onto alkenes with the formation of five-, six-, and eight-membered rings. The immediate products of the cyclizations onto alkenes are alpha-[(aryltelluro)methyl] ketones and the chemistry of these relatively unstable species is briefly described. Treatment with hydrogen peroxide affords alpha-methylene ketones in high yield. When elimination of the aryl telluro group is not possible the alpha-[(aryltelluro)methyl] ketones are stable species that may subsequently be employed in further radical chain reactions, for example with tributyltin hydride and methyl acrylate. Cyclization onto alkynes yields alpha-[(aryltelluro)methylene] ketones which are stable species and which take part in substitution reactions with higher order cuprates or with diphenyl diselenide.
• Bachi, Mario D.; Denenmark, Daniella, Heterocycles, 1989, vol. 28, # 2, p. 583 - 588
  作者：Bachi, Mario D.、Denenmark, Daniella

  DOI：——

  日期：——