2-benzoylmethylene-1,3-oxazolidine

• 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-benzoylmethylene-1,3-oxazolidine
• 英文别名: 2-(benzoylmethylene)-oxazolidine；2-(1,3-Oxazolidin-2-ylidene)-1-phenylethanone
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: CZEMJSPBCCOLOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  百菌清 、 2-benzoylmethylene-1,3-oxazolidine 生成 2,4,5-trichloro-6-(1-(oxazolidin-2-ylidene)-2-oxo-2-phenylethyl)isophthalonitrile
  参考文献：
  名称：

  Facile Route to 1,3-Diazaheterocycle-Fused [1,2b]Isoquinolin-1(2H)-one Derivatives via Substitution-Cyclization Reactions

  摘要：

  The substitution-cyclization reaction of heterocyclic ketene aminals with polyhalo isophthalonitrile in the presence of t-BuOK to form 1,3-diazaheterocycle fused [1,2-b]isoquinolin-1(2H)-imines, followed by hydrolysis with 1N HCl, provides a concise and efficient route for the synthesis of highly functional polyhalo 1,3-diazaheterocycle fused [1,2-b]isoquinolin-1(2H)-ones.

  DOI：

  10.1021/cc900121c
• 作为产物：
  描述：

  2-phenacylthio-1,3-oxazoline 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以34%的产率得到2-benzoylmethylene-1,3-oxazolidine
  参考文献：
  名称：

  Gueyrard, David; Grumel, Valerie; Leoni, Onofrio, Heterocycles, 2000, vol. 52, # 2, p. 827 - 843

  摘要：

  DOI：

文献信息

• Regioselective Synthesis of Heterocyclic Ketene N,N-, N,O- and N,S-acetals in Aqueous Medium
  作者：Langpoklakpam Gellina Chanu、Okram Mukherjee Singh、Sang-Hun Jang、Sang-Gyeong Lee

  DOI：10.5012/bkcs.2010.31.04.859

  日期：2010.4.20

  The reactions of ketene dithioacetals with ethane-1,2-diamine, propane-1,3-diamine, 2-aminoethanol, 3-aminopropanol, and 2-aminoethanethiol in ordinary water in the absence of any acid/base catalyst afforded the heterocyclic ketene N,N-, N,O- and N,S-acetals in good yields.

  在没有任何酸/碱催化剂的情况下，乙烯酮二硫缩醛与乙烷-1,2-二胺、丙烷-1,3-二胺、2-氨基乙醇、3-氨基丙醇和2-氨基乙硫醇在普通水中反应得到杂环乙烯酮N,N-、N,O- 和 N,S-缩醛的收率良好。
• One-Pot Electrochemical Synthesis of Fused Indole Derivatives Containing Active Hydroxyl Groups in Aqueous Medium
  作者：Cheng-Chu Zeng、Fu-Jian Liu、Da-Wei Ping、Li-Ming Hu、Yuan-Li Cai、Ru-Gang Zhong

  DOI：10.1021/jo901091s

  日期：2009.8.21

  An novel and convenient electrochemical approach was developed for the synthesis of indole derivatives from catechols and α-oxoheterocyclic ketene N,O-acetals. This method provides an environmentally benign access to fused indole derivatives containing active hydroxyls and carbonyl under mild reaction conditions.

  开发了一种新型便捷的电化学方法，用于从儿茶酚和α-氧杂环烯酮N，O-乙缩醛合成吲哚衍生物。该方法在温和的反应条件下提供了对环境友好的含有活性羟基和羰基的稠合吲哚衍生物的途径。
• Electrochemical oxidation of catechols in the presence of ketene N,O-acetals: indole formation versus α-arylation
  作者：Yue-Xia Bai、Da-Wei Ping、R. Daniel Little、Hong-Yu Tian、Li-Ming Hu、Cheng-Chu Zeng

  DOI：10.1016/j.tet.2011.09.126

  日期：2011.12

  Anodic oxidation of catechols has been investigated in the presence of ketene N,O-acetals using cyclic voltammetry and constant current electrolysis methods. The results show that in the presence of ketene N,O-acetals, the anodic oxidation of 4-methylcatechol affords α-arylated products in satisfactory yields. Meanwhile, indoles can be synthesized from simple 3-substituted catechols or catechol itself

  使用循环伏安法和恒流电解方法研究了在烯酮N，O-乙缩醛存在下对儿茶酚的阳极氧化。结果表明，在乙烯酮N，O-乙缩醛的存在下，4-甲基邻苯二酚的阳极氧化可提供令人满意的产率的α-芳基化产物。同时，可以根据ECEC机理由简单的3-取代的邻苯二酚或邻苯二酚本身合成吲哚。另外，通过简单地改变电解质溶液的组成，α-芳基化或吲哚形成可能是主要途径。
• A Novel Abnormal Michael Reaction of 2-Acylmethyl-4,4-dimethyl-2-oxazolines with Acetylenic Ketones and Esters
  作者：Yasuo Tohda、Takeshi Yanagidani、Noriko Asaka

  DOI：10.1246/bcsj.20150397

  日期：2016.7.15

  abnormal Michael reaction of an active methylene compound, 2-acylmethyl-4,4-dimethyl-2-oxazoline with acetylenic ketone in acetonitrile is reported. The reaction accompanies 1,3-migration of the acyl group of the substrate to give 2-(3-acyl-1-buten-4-on-1-yl)-2-oxazoline, which was easily cyclized to 5-acyl-2-pyridone derivatives by treatment with silica gel. Selectivity of the reaction depends on bulkiness

  报告了活性亚甲基化合物 2-酰基甲基-4,4-二甲基-2-恶唑啉与乙腈在乙腈中发生异常迈克尔反应的第一个例子。该反应伴随着底物酰基的 1,3-迁移生成 2-(3-acyl-1-buten-4-on-1-yl)-2-oxazoline，它很容易环化为 5-acyl- 2-吡啶酮衍生物通过硅胶处理。反应的选择性取决于底物和试剂的所有取代基的体积。选择性被解释为通过空间和电子因素降低初始阴离子加合物中间体的动力学酸度。
• Synthesis of Bicyclic Pyridones via Cyclocondensation of Heterocyclic Ketene Aminals with β-Ketoester Enol Tosylates
  作者：Jun Lin、Sheng-Jiao Yan、Yan-Fei Niu、Rong Huang

  DOI：10.1055/s-0029-1217984

  日期：2009.10

  A series of novel bicyclic pyridones were easily prepared by cyclic condensation of heterocyclic ketene aminals with β-keto ester enol tosylates in the presence of a base to give products in excellent yields (80-95%).

  在碱的存在下，通过杂环烯酮胺醛与 β-酮酯烯醇甲苯磺酸酯的环缩合反应，可以很容易地制备一系列新型双环吡啶酮，以优异的产率 (80-95%) 得到产物。