1-benzyl-5-chloro-3-phenyl-2(1H)-pyrazinone | 138610-74-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-benzyl-5-chloro-3-phenyl-2(1H)-pyrazinone
• 英文别名: 1-benzyl-5-chloro-3-phenylpyrazin-2-one
• CAS: 138610-74-9
• 化学式: C₁₇H₁₃ClN₂O
• 分子量: 296.756
• InChiKey: GGSIXFGSDHCDLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-5-chloro-3-phenyl-2(1H)-pyrazinone 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 以84%的产率得到1-benzyl-3-phenyl-2(1H)-pyrazinone
  参考文献：
  名称：

  Expanding the substitution pattern of 2(1H)-pyrazinones via Suzuki and Heck reactions

  摘要：

  Various 3,5-dichloropyrazinones were substituted at the C-3 position with (hetero)aryl, alkyl and alkenyl groups by means of Suzuki and Heck reactions. The methodology could be extended to reactions on the far less reactive C-5 position by transhalogenation of the 5-Cl substituent to a 5-Br or a 5-I group prior to performing the cross-coupling. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.02.056
• 作为产物：
  描述：

  1-苄基-3,5-二氯吡嗪-2(1h)-酮 、 phenylmagnesium bromide 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.17h， 以90%的产率得到1-benzyl-5-chloro-3-phenyl-2(1H)-pyrazinone
  参考文献：
  名称：

  Cycloadducts of ethene with 2(1H)-pyrazinones and their conversion into 2,5-diazabicyclo[2.2.2]octane-3,6-diones.

  摘要：

  Cycloaddition of variously substituted 2(1H)-pyrazinones with ethene and subsequent hydrolysis of the adducts 2 provides a general and efficient route to the title compounds 3. Compound 3m was used as a building block for a structural analogue of gliotoxin.

  DOI：

  10.1016/s0040-4020(01)96214-3

文献信息

• The effect of pressure on microwave-enhanced Diels–Alder reactions. A case study
  作者：Nadya Kaval、Wim Dehaen、C. Oliver Kappe、Erik Van der Eycken

  DOI：10.1039/b315150f

  日期：——

  It is demonstrated that microwave-assisted Diels–Alder reactions of substituted 2(1H)-pyrazinones with ethylene are significantly more effective utilizing pre-pressurized (up to 10 bar) reaction vessels.

  研究表明，利用微波辅助取代的 2(1H)-吡嗪酮与乙烯的 DielsâAlder 反应，利用预压（高达 10 巴）反应容器效果显著。
• Stereo- and regiochemistry in the (asymmetric) cycloaddition reaction of 5-chloro-2(1 H )-pyrazinones with cyclic and monosubstituted alkenes and with a N -acryloyl substituted chiral auxiliary
  作者：Frederik J.R Rombouts、David A.J Vanraes、Jo Wynendaele、Patrick K Loosen、Ingrid Luyten、Suzanne Toppet、Frans Compernolle、Georges J Hoornaert

  DOI：10.1016/s0040-4020(01)00179-x

  日期：2001.4

  The cycloaddition of 5-chloro-2(1H)-pyrazinones 1 with various dienophiles was used to generate the corresponding 2,5-diazabicyclo[2.2.2]octanes. Following reduction or hydrolysis of the bridged adducts, the regio- and stereochemical structure was determined by analysis of the coupling and NOE patterns in the 1H NMR spectra. With symmetric dienophiles the endo adducts are formed exclusively. The regiochemistry

  5-氯-2（1 H）-吡嗪酮1与各种亲二烯体的环加成反应用于生成相应的2,5-二氮杂双环[2.2.2]辛烷。桥联加合物还原或水解后，通过分析1 H NMR光谱中的偶联和NOE图谱确定区域和立体化学结构。对于对称的双亲二烯体，仅形成内加合物。1与丙烯酸甲酯和乙基乙烯基醚反应的区域化学，以及N-丙烯酰基取代的手性助剂（4 S）-4-异丙基-1-甲基四氢-2 H的不对称诱导-咪唑-2-酮在很大程度上取决于1的3个取代基的给电子或吸引性质和大小。
• Cycloadducts of ethene with 2(1H)-pyrazinones functionalisation and reduction to 2,5-diazabicyclo[2.2.2]octan-3-ones.
  作者：Patrick K. Loosen、Masoumeh F. Khorasani、Suzanne M. Toppet、Georges J. Hoornaert

  DOI：10.1016/s0040-4020(01)96215-5

  日期：1991.11

  The title compounds 4 were prepared via Diels-Alder reaction of 3,5-dichloro-2(1H)-pyrazinones 1 with ethene, followed by catalytic reduction of the iminochloride group generated in the cycloadducts 2. Substitution of the iminochloride group with various nucleophiles afforded the 6-functionalised analogues of 2. Their reduction can lead to 6-substituted derivatives of compounds 4. One example is given.
• Expanding the substitution pattern of 2(1H)-pyrazinones via Suzuki and Heck reactions
  作者：Rasha Azzam、Wim M. De Borggraeve、Frans Compernolle、Georges J. Hoornaert

  DOI：10.1016/j.tet.2005.02.056

  日期：2005.4

  Various 3,5-dichloropyrazinones were substituted at the C-3 position with (hetero)aryl, alkyl and alkenyl groups by means of Suzuki and Heck reactions. The methodology could be extended to reactions on the far less reactive C-5 position by transhalogenation of the 5-Cl substituent to a 5-Br or a 5-I group prior to performing the cross-coupling. (c) 2005 Elsevier Ltd. All rights reserved.
• Cycloadducts of ethene with 2(1H)-pyrazinones and their conversion into 2,5-diazabicyclo[2.2.2]octane-3,6-diones.
  作者：Patrick K. Loosen、Mayoka G. Tutonda、Masoumeh F. Khorasani、Frans Compernolle、Georges J. Hoornaert

  DOI：10.1016/s0040-4020(01)96214-3

  日期：1991.11

  Cycloaddition of variously substituted 2(1H)-pyrazinones with ethene and subsequent hydrolysis of the adducts 2 provides a general and efficient route to the title compounds 3. Compound 3m was used as a building block for a structural analogue of gliotoxin.