(2,4-dihydro-1H-benzo[d][1,3]oxazin-2-yl)(phenyl)methanone | 90284-44-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,4-dihydro-1H-benzo[d][1,3]oxazin-2-yl)(phenyl)methanone
• 英文别名: Methanone, (1,4-dihydro-2H-3,1-benzoxazin-2-yl)phenyl-；2,4-dihydro-1H-3,1-benzoxazin-2-yl(phenyl)methanone
• CAS: 90284-44-9
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: CFUWUAUHXZIICW-UHFFFAOYSA-N

物化性质

• 沸点：
  436.0±45.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2,4-dihydro-1H-benzo[d][1,3]oxazin-2-yl)(phenyl)methanone 在 4-二甲氨基吡啶 、 碘 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  通过邻群协助策略在咪唑合成中使用TosMIC作为C1N1“双原子合成子”。

  摘要：

  我们报告了I2 / FeCl3共促进的芳基甲基酮，2-氨基苄醇和对甲苯磺酰基甲基异氰酸酯（TosMIC）的邻域（-CH2OH）协助的正式[2 + 2 + 1]环化反应。这是在合成咪唑时使用Van Leusen试剂作为独特的C1N1“双原子合成子”的新例子。初步机理研究表明，TsCH2NH2可能是该反应的关键中间体。此外，该反应不仅解锁了咪唑合成的新策略，而且还开发了TosMIC的新反应性。

  DOI：

  10.1021/acs.orglett.9b04060
• 作为产物：
  描述：

  邻氨基苯甲醇 、 3,4-二羟基苯乙酮 以 甲醇 为溶剂， 反应 0.25h， 以90%的产率得到(2,4-dihydro-1H-benzo[d][1,3]oxazin-2-yl)(phenyl)methanone
  参考文献：
  名称：

  Acid-mediated four-component tandem cyclization: Access to multifused 1,3-benzoxazine frameworks

  摘要：

  An acid-mediated multicomponent reaction has been developed for the direct synthesis of multifused 1,3-benzoxazine derivatives from simple and readily available arylglyoxal monohydrates and 2-aminobenzyl alcohols under mild conditions. This novel protocol is proposed to proceed through intramolecular poly-heterocyclizations, thus leading to the formation of three new rings and six new chemical bonds, including four C-N and two C-O bonds. (C) 2018 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2018.10.059

文献信息

• I₂-Promoted Multicomponent Dicyclization and Ring-Opening Sequences: Direct Synthesis of Benzo[<i>e</i>][1,4]diazepin-3-ones via Dual C–O Bond Cleavage
  作者：Xiao Geng、Can Wang、Chun Huang、Peng Zhao、You Zhou、Yan-Dong Wu、An-Xin Wu

  DOI：10.1021/acs.orglett.9b02789

  日期：2019.9.20

  [4 + 2+1] annulation of aryl methyl ketones and 2-aminobenzyl alcohols for the synthesis of benzo[e][1,4]diazepin-3-ones is reported. This reaction successfully affords diverse seven-membered ring lactams via dual C–O bond cleavage. A preliminary mechanistic study showed that a multicomponent dicyclization and ring-opening sequence might occur, with the introduction of methyl sulfide proposed as the

  报道了一种新颖有效的芳基甲基酮和2-氨基苄醇的正式[4 + 2 + 1]环合反应，用于合成苯并[ e ] [1,4]二氮杂-3-酮。该反应通过双C-O键裂解成功提供了多种七元环内酰胺。初步的机理研究表明，可能会发生多组分二环化和开环过程，而提议的最后一步是引入甲基硫醚。具有温和的反应条件和广泛的底物范围的这种有效策略在化学和医学中具有潜在的应用。
• Reprint of: Acid-mediated four-component tandem cyclization: Access to multifused 1,3-benzoxazine frameworks
  作者：Jungang Wang、Rongrong Zhou、Shiyi Zhuang、Anxin Wu

  DOI：10.1016/j.tet.2019.02.058

  日期：2019.3

  An acid-mediated multicomponent reaction has been developed for the direct synthesis of multifused 1,3-benzoxazine derivatives from simple and readily available arylglyoxal monohydrates and 2-aminobenzyl alcohols under mild conditions. This novel protocol is proposed to proceed through intramolecular poly-heterocyclizations, thus leading to the formation of three new rings and six new chemical bonds, including four C-N and two C-O bonds. (C) 2019 Published by Elsevier Ltd.
• Employing TosMIC as a C1N1 “Two-Atom Synthon” in Imidazole Synthesis by Neighboring Group Assistance Strategy
  作者：Xiao Geng、Can Wang、Chun Huang、Yang Bao、Peng Zhao、You Zhou、Yan-Dong Wu、Ling-ling Feng、An-Xin Wu

  DOI：10.1021/acs.orglett.9b04060

  日期：2020.1.3

  I2/FeCl3-co-promoted formal [2 + 2+1] annulation of aryl methyl ketones, 2-aminobenzyl alcohols, and p-toluenesulfonylmethyl isocyanide (TosMIC) by neighboring group (-CH2OH) assistance. This is a novel example of using the Van Leusen reagent as a unique C1N1 "two-atom synthon" in the synthesis of imidazoles. Preliminary mechanism studies showed that TsCH2NH2 might be the key intermediate in this reaction

  我们报告了I2 / FeCl3共促进的芳基甲基酮，2-氨基苄醇和对甲苯磺酰基甲基异氰酸酯（TosMIC）的邻域（-CH2OH）协助的正式[2 + 2 + 1]环化反应。这是在合成咪唑时使用Van Leusen试剂作为独特的C1N1“双原子合成子”的新例子。初步机理研究表明，TsCH2NH2可能是该反应的关键中间体。此外，该反应不仅解锁了咪唑合成的新策略，而且还开发了TosMIC的新反应性。
• Acid-mediated four-component tandem cyclization: Access to multifused 1,3-benzoxazine frameworks
  作者：Jungang Wang、Rongrong Zhou、Shiyi Zhuang、Anxin Wu

  DOI：10.1016/j.tet.2018.10.059

  日期：2018.12

  An acid-mediated multicomponent reaction has been developed for the direct synthesis of multifused 1,3-benzoxazine derivatives from simple and readily available arylglyoxal monohydrates and 2-aminobenzyl alcohols under mild conditions. This novel protocol is proposed to proceed through intramolecular poly-heterocyclizations, thus leading to the formation of three new rings and six new chemical bonds, including four C-N and two C-O bonds. (C) 2018 Published by Elsevier Ltd.