tert-butoxycarbonylimino-[(3,5-dimethyl-4-oxo-[1,3,5]triazinan-1-yl)methyl]carbamic acid tert-butyl ester | 911857-61-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪烷类
• 英文名称: tert-butoxycarbonylimino-[(3,5-dimethyl-4-oxo-[1,3,5]triazinan-1-yl)methyl]carbamic acid tert-butyl ester
• 英文别名: tert-butyl (((tert-butoxycarbonyl)imino)(3,5-dimethyl-4-oxo-1,3,5-triazinan-1-yl)methyl)carbamate；tert-butyl(((tert-butoxycarbonyl)imino)(3,5-dimethyl-4-oxo-1,3,5-triazinan-1-yl)methyl)carbamate；Tert-butyl (((tert-butoxycarbonyl)imino)(3,5-dimethyl-4-oxo-1,3,5-triazinan-1-yl)methyl)carbamate；tert-butyl N-[(3,5-dimethyl-4-oxo-1,3,5-triazinan-1-yl)-[(2-methylpropan-2-yl)oxycarbonylamino]methylidene]carbamate
• CAS: 911857-61-9
• 化学式: C₁₆H₂₉N₅O₅
• 分子量: 371.437
• InChiKey: XJYFNWQRTHOSSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butoxycarbonylimino-[(3,5-dimethyl-4-oxo-[1,3,5]triazinan-1-yl)methyl]carbamic acid tert-butyl ester 在 碳酸氢钠 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 2-(3,5-dimethyl-4-oxo-[1,3,5]triazin-1-yl)-6-methyl-4-(4-nitrophenyl)-1,4-dihydropyrimidine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Concise Synthesis of Guanidine-Containing Heterocycles Using the Biginelli Reaction

  摘要：

  Two general methods for the synthesis of 2-imino-5-carboxy-3,4-dihydropyrimidines were developed using the three-component Biginelli reaction. The first method utilizes pyrazole carboxamidine, a beta-ketoester, and an aldehyde in an initial Biginelli reaction. After Boc protection, these products undergo aminolysis and acidic deprotection to generate 2-imino-5-carboxy-3,4-dihydropyrimidines in a four-step sequence. The second method utilizes a triazone-protected guanidine, a beta-ketoester, and an aldehyde in a Biginelli reaction. Acidic cleavage of the triazone yields 2-imino-5-carboxy-3,4-dihydropyrimidines in a two-step sequence. We also describe the further elaboration of several of these products using a tethered Biginelli reaction to give triazaacenaphthalene structures similar to those found in crambescidin and batzelladine alkaloids.

  DOI：

  10.1021/jo061199m
• 作为产物：
  描述：

  5-benzyl-1,3-dimethyl-[1,3,5]triazinan-2-one 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 65.0~70.0 ℃ 、5.17 MPa 条件下， 反应 42.0h， 生成 tert-butoxycarbonylimino-[(3,5-dimethyl-4-oxo-[1,3,5]triazinan-1-yl)methyl]carbamic acid tert-butyl ester
  参考文献：
  名称：

  Concise Synthesis of Guanidine-Containing Heterocycles Using the Biginelli Reaction

  摘要：

  Two general methods for the synthesis of 2-imino-5-carboxy-3,4-dihydropyrimidines were developed using the three-component Biginelli reaction. The first method utilizes pyrazole carboxamidine, a beta-ketoester, and an aldehyde in an initial Biginelli reaction. After Boc protection, these products undergo aminolysis and acidic deprotection to generate 2-imino-5-carboxy-3,4-dihydropyrimidines in a four-step sequence. The second method utilizes a triazone-protected guanidine, a beta-ketoester, and an aldehyde in a Biginelli reaction. Acidic cleavage of the triazone yields 2-imino-5-carboxy-3,4-dihydropyrimidines in a two-step sequence. We also describe the further elaboration of several of these products using a tethered Biginelli reaction to give triazaacenaphthalene structures similar to those found in crambescidin and batzelladine alkaloids.

  DOI：

  10.1021/jo061199m

文献信息

• A Mild and General One-Pot Synthesis of Densely Functionalized Diaryliodonium Salts
  作者：Linlin Qin、Bao Hu、Kiel D. Neumann、Ethan J. Linstad、Katelyenn McCauley、Jordan Veness、Jayson J. Kempinger、Stephen G. DiMagno

  DOI：10.1002/ejoc.201500986

  日期：2015.9

  Diaryliodonium salts are powerful and widely used arylating agents in organic chemistry. Here we report a scalable, synthesis of densely functionalized diaryliodonium salts from aryl iodides under mild conditions. This two-step, one-pot process has remarkable functional group tolerance, is compatible with commonly employed acid-labile protective group strategies, avoids heavy metal and transition metal

  二芳基碘鎓盐是有机化学中强大且广泛使用的芳基化剂。在这里，我们报告了在温和条件下从芳基碘化物大规模合成密集官能化二芳基碘鎓盐的方法。这种两步一锅法具有显着的官能团耐受性，与常用的酸不稳定保护基策略兼容，避免重金属和过渡金属试剂，并为 PET 成像剂的稳定前体提供了直接途径。
• [EN] COMPOUND TARGETING NOREPINEPHRINE TRANSPORTER<br/>[FR] COMPOSÉ CIBLANT UN TRANSPORTEUR DE NORÉPINÉPHRINE
  申请人：UNIV WUERZBURG J MAXIMILIANS

  公开号：WO2020148154A1

  公开（公告）日：2020-07-23

  The invention concerns a compound according to following formula, wherein R1 is an F or an I residue.

  这项发明涉及一种化合物，其化学式如下，其中R1是F或I残基。
• COMPOUND TARGETING NOREPINEPHRINE TRANSPORTER
  申请人：Julius-Maximilians-Universität Würzburg

  公开号：EP3682906A1

  公开（公告）日：2020-07-22

  The invention concerns a compound according to following formula wherein R1 is a halogen residue.

  本发明涉及一种符合下式的化合物 其中 R1 为卤素残基。
• [EN] RADIOIODINATED COMPOUNDS<br/>[FR] COMPOSÉS RADIOIODÉS
  申请人：NUTECH VENTURES

  公开号：WO2015147950A3

  公开（公告）日：2016-03-03
• RADIOIODINATED COMPOUNDS
  申请人：Nutech Ventures

  公开号：EP3089962B1

  公开（公告）日：2019-03-13