3-Benzyl-6-isobutyl-5-methyl-1H-pyrazin-2-one | 155650-93-4

• 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: 3-Benzyl-6-isobutyl-5-methyl-1H-pyrazin-2-one
• 英文别名: 3-benzyl-5-methyl-6-(2-methylpropyl)-1H-pyrazin-2-one
• CAS: 155650-93-4
• 化学式: C₁₆H₂₀N₂O
• 分子量: 256.348
• InChiKey: AXCCDBDQFZZTQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Benzyl-6-isobutyl-5-methyl-1H-pyrazin-2-one 在 diclazuril 、 氘代甲醇 、 重水 作用下， 以100%的产率得到3-[dideuterio(phenyl)methyl]-5-methyl-6-(2-methylpropyl)-1H-pyrazin-2-one
  参考文献：
  名称：

  Amino Acids and Peptides. XLVI. Introduction of Carboxyl Function into Pyrazinone by Using Newly Developed Procedure for Pyrazinone Ring Formation: Observation of Immediate Decarboxylation.

  摘要：

  通过一种新开发的从含有天冬氨酸或谷氨酸的二肽氯甲基酮形成吡嗪酮环的方法，可以很容易地将羧基功能引入吡嗪酮环：在反应过程中，由于2(1H)-吡嗪酮的第3位电子密度较低，从第3位的羧甲基快速脱羧发生在2(1H)-吡嗪酮上。

  DOI：

  10.1248/cpb.44.2037
• 作为产物：
  描述：

  H-Phe-Leu-CH3*HCl 以 甲醇 为溶剂， 反应 2.0h， 以73.2%的产率得到3-Benzyl-6-isobutyl-5-methyl-1H-pyrazin-2-one
  参考文献：
  名称：

  Amino Acids and Peptides. XLI. 1:2 Facile Synthesis of 5-Methyl-2(1H)- pyrazinone Derivatives from Dipeptidyl Chloromethyl Ketones 3

  摘要：

  5-Methyl-2(1H)-pyrazinone derivatives were easily synthesized by short reflux of dipeptidyl chloromethyl ketone hydrochlorides in MeOH.

  DOI：

  10.1016/0040-4020(95)00385-l

文献信息

• Amino Acids and Peptides. XLVI. Introduction of Carboxyl Function into Pyrazinone by Using Newly Developed Procedure for Pyrazinone Ring Formation: Observation of Immediate Decarboxylation.
  作者：Hiroaki TAGUCHI、Toshio YOKOI、Yoshio OKADA

  DOI：10.1248/cpb.44.2037

  日期：——

  The carboxyl function was easily introduced into a pyrazinone ring by means of a newly developed procedure for pyrazinone ring formation from Asp- or Glu-containing dipeptidyl chloromethyl ketones : during the reaction, rapid decarboxylation from a carboxymethyl group at position 3 of 2(1H)-pyrazinone occurred due to the low electron density at position 3 of 2 (1H)-pyrazinone.

  通过一种新开发的从含有天冬氨酸或谷氨酸的二肽氯甲基酮形成吡嗪酮环的方法，可以很容易地将羧基功能引入吡嗪酮环：在反应过程中，由于2(1H)-吡嗪酮的第3位电子密度较低，从第3位的羧甲基快速脱羧发生在2(1H)-吡嗪酮上。
• Amino Acids and Peptides. XL. Synthesis of Ac-Tyr-Val-Ala-Asp-MCA Using Newly Developed Acetylating Reagent.
  作者：Hiroaki TAGUCHI、Kenichi HIRANO、Toshio YOKOI、Keiichi ASADA、Yoshio OKADA

  DOI：10.1248/cpb.43.1336

  日期：——

  utylpyrazine was prepared by cyclization of H-Phe-Leu-CH2Cl, followed by acetylation with acetic anhydride. This pyrazine derivative can react with amino groups of amino acids or peptides to produce acetyl amino acids or acetyl peptides without acetylation of hydroxy group of Tyr, Ser and Thr. Using this acetylating reagent, Ac-Tyr-Val-Ala-Asp-MCA, which is a specific substrate of the interleukin-I

  通过对H-Phe-Leu-CH2Cl进行环化，然后用乙酸酐进行乙酰化，制得2-乙酰氧基-3-苄基-5-甲基-6-异丁基吡嗪。该吡嗪衍生物可以与氨基酸或肽的氨基反应以产生乙酰基氨基酸或乙酰基肽，而不会使Tyr，Ser和Thr的羟基乙酰化。使用该乙酰化试剂，制备了白介素I（IL-1）加工酶的特异性底物Ac-Tyr-Val-Ala-Asp-MCA。
• Unexpected reaction of dipeptidyl chloromethyl ketone during acid hydrolysis
  作者：Hiroaki Taguchi、Toshio Yokoi、Fumiyo Kasuya、Yasuhiro Nishiyama、Miyoshi Fukui、Yoshio Okada

  DOI：10.1039/c39940000247

  日期：——

  Amino acid recovery of dipeptidyl chloromethyl ketones is remarkably low owing to the formation of 2-hydroxy-3, 6-dialkyl-5-methylpyrazine during acid hydrolysis.

  由于在酸水解过程中会形成2-羟基-3,6-二烷基-5-甲基吡嗪，二肽氯甲基酮的氨基酸回收率非常低。
• Simple approach towards the synthesis of 5-methyl-2-hydroxypyrazine derivatives from dipeptidyl chloromethyl ketones
  作者：Yoshio Okada、Hiroaki Taguchi、Yasuhiro Nishiyama、Toshio Yokoi

  DOI：10.1016/0040-4039(94)88031-x

  日期：1994.2

  5-Methyl-2-hydroxypyrazine derivatives were easily synthesized by short reflux of dipeptidyl chloromethyl ketone hydrochlorides in MeOH.
• Yokoi, Toshio; Taguchi, Hiroaki; Nishiyama, Yasuhiro, Journal of Chemical Research, Miniprint, 1997, # 1, p. 171 - 185
  作者：Yokoi, Toshio、Taguchi, Hiroaki、Nishiyama, Yasuhiro、Igarashi, Kazuo、Kasuya, Fumiyo、Okada, Yoshio

  DOI：——

  日期：——