1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-phenylethan-1-one | 18212-83-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-phenylethan-1-one
• 英文别名: 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-phenylethanone；1-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-2-phenyl-ethanone；1-(2,3-Dihydro-1,4-benzodioxin-6-yl)-2-phenylethanone
• CAS: 18212-83-4
• 化学式: C₁₆H₁₄O₃
• mdl: MFCD01333467
• 分子量: 254.285
• InChiKey: WEKCFNFPWZCSIS-UHFFFAOYSA-N

物化性质

• 沸点：
  426.8±44.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.187
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-phenylethan-1-one 在 盐酸 、 sodium tetrahydroborate 作用下， 以 水 为溶剂， 反应 320.0h， 生成 6-(1-ethoxy-2-phenylethyl)-2,3-dihydro-1,4-benzodioxine
  参考文献：
  名称：

  Hydrochloric acid as an efficient catalyst for intermolecular condensation of alcohols. A simple and highly efficient synthesis of unsymmetrical ethers from benzylic alcohols and alkanols

  摘要：

  Benzylic alcohols and diarylmethanols with electron-donating substituents in the aromatic ring reacted with aliphatic alcohols in the presence of a catalytic amount of HCl to give the corresponding alkyl arylmethyl ethers. The reactivity of diarylmethanols in the intermolecular dehydration depended on the nature of substituents in the aromatic rings and structure of aliphatic alcohol.

  DOI：

  10.1134/s107042801509002x
• 作为产物：
  描述：

  1-(2,3-二氢-1,4-苯并二氧杂环己-6-基)-2-羟基乙烷酮 在 二氯化双(三环己基膦)镍(II) 、 三乙胺 、 sodium t-butanolate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 0.67h， 生成 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-phenylethan-1-one
  参考文献：
  名称：

  Arylation of α-pivaloxyl ketones with arylboronic reagents via Ni-catalyzed sp3 C–O activation

  摘要：

  开发了一种通过镍催化的sp3 C–O活化将α-皮伐氧基酮与α-芳基酮进行Suzuki–Miyaura耦合的方法。本研究提供了一种便利的方法，以便从易得的α-羟基羰基化合物构建α-芳基化产物。

  DOI：

  10.1039/c1cc11193k

文献信息

• Palladium-Catalyzed Denitrative α-Arylation of Ketones with Nitroarenes
  作者：Zhirong Li、Yonggang Peng、Tao Wu

  DOI：10.1021/acs.orglett.0c04104

  日期：2021.2.5

  The palladium-catalyzed α-arylation of ketones with readily available nitroarenes and nitroheteroarenes provides access to useful α-aryl and α-heteroaryl ketones. The use of the Pd/BrettPhos catalysts was critical to achieve high efficiency for these transformations, whereas other catalysts led to decreased yields or no conversions. The intramolecular type substrate was also applied in this methodology

  钯催化α -用容易获得的硝基芳烃和芳基化nitroheteroarenes酮的提供访问有用的α -芳基和α -杂芳基酮。Pd / BrettPhos催化剂的使用对于实现这些转化的高效率至关重要，而其他催化剂则导致收率降低或没有转化。分子内型底物也用于该方法中，得到色酮衍生物。聚芳族羰基化合物可以通过多组分串联反应而容易地获得，经由亲核芳族取代（S Ñ AR）或交叉偶联反应，接着此denitrative芳基化。动力学实验表明，硝基苯的电子效应比酮的电子效应对反应速率的影响更大。
• Palladium-Catalyzed Carbonylative Negishi-type Coupling of Aryl Iodides with Benzyl Chlorides
  作者：Xiao-Feng Wu、Johannes Schranck、Helfried Neumann、Matthias Beller

  DOI：10.1002/asia.201100627

  日期：2012.1.2

  Do the competition: The synthesis of 1,2‐diarylethanones has been accomplished using the palladium‐catalyzed coupling of aryl iodides and CO/benzyl chlorides or benzoyl chlorides. These reactions proceed smoothly in the presence of zinc powder to afford the products in moderate to excellent yields.

  参加竞争：1,2-二芳基酮的合成是通过芳基碘化物与CO /苄基氯或苯甲酰氯的钯催化偶联完成的。在锌粉存在下，这些反应平稳进行，以中等至极好的收率提供产物。
• Direct synthesis of ethers from aldehydes and ketones. One-pot reductive etherification of benzaldehydes, alkyl aryl ketones, and benzophenones
  作者：S. S. Mochalov、A. N. Fedotov、E. V. Trofimova、N. S. Zefirov

  DOI：10.1134/s1070428016040047

  日期：2016.4

  Benzyl alcohols formed by the reduction of benzaldehydes, alkyl aryl ketones, and benzophenones with sodium tetrahydridoborate in alcohols undergo in situ etherification with the solvent in the presence of a catalytic amount of HCl. Thus the process may be regarded as one-pot transformation of carbonyl compounds into the corresponding benzyl ethers. The yields of ethers depend on the substituent nature

  通过在醇中催化量的四氢硼酸钠将苯甲醛，烷基芳基酮和二苯甲酮还原而形成的苄醇在催化量的HCl的存在下与溶剂进行原位醚化。因此，该方法可以被认为是羰基化合物一锅转化为相应的苄基醚。醚的产率取决于初始羰基化合物的芳族片段中的取代基性质以及用作还原介质的醇。
• 10.1007/s11426-024-2019-1
  作者：Wang, Xiuhua、Zhou, Jianrong Steve

  DOI：10.1007/s11426-024-2019-1

  日期：——

  Asymmetric reductive amination directly converts ketones and amines to alkylamines, which are important motifs in medicines. We report that cationic nickel complexes of chiral diphosphines promote enantioselective reductive amination of benzylic ketones with both arylamines and benzhydrazide. Isopropanol was used as a safe and cheap source of hydrogen instead of formic acid. The reaction can be readily

  不对称还原胺化直接将酮和胺转化为烷基胺，这是药物中的重要基序。我们报道了手性二膦的阳离子镍配合物促进了苯甲基酮与芳基胺和苯甲酰肼的对映选择性还原胺化。使用异丙醇代替甲酸作为安全且廉价的氢源。该反应可以很容易地应用于二芳基乙胺（一类神经活性物质）的简明合成。
• Synthesis of symmetrical α-alkyl- and α-arylalkylbenzyl and diarylmethyl ethers by HCl-catalyzed intermolecular dehydration
  作者：S. S. Mochalov、A. N. Fedotov、E. V. Trofimova、N. S. Zefirov

  DOI：10.1134/s1070428017100050

  日期：2017.10

  alpha-Alkyl-, alpha-arylalkyl-, and alpha-aryl-substituted benzyl alcohols were converted into the corresponding symmetrical dibenzyl ethers in the presence of a catalytic amount of 10% aqueous HCl both in methylene chloride and under solvent-free conditions. Analogous reactions in dioxane and on heating afforded mainly the corresponding arylalkenes, whereas symmetrical dibenzyl ethers were formed as minor products.