dimethyl 1,4-dihydro-1,2,4,5-tetrazine-3,6-dicarboxylate | 3787-10-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dimethyl 1,4-dihydro-1,2,4,5-tetrazine-3,6-dicarboxylate
• 英文别名: dimethyl dihydro-1,2,4,5-tetrazine-3,6-dicarboxylate
• CAS: 3787-10-8
• 化学式: C₆H₈N₄O₄
• mdl: MFCD00154543
• 分子量: 200.154
• InChiKey: BWMHDXXBRBGHHJ-UHFFFAOYSA-N

物化性质

• 熔点：
  168-170 °C(Solv: water (7732-18-5))
• 沸点：
  262.6±23.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  dimethyl 1,4-dihydro-1,2,4,5-tetrazine-3,6-dicarboxylate 在 盐酸 、 sodium nitrite 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以98%的产率得到1,2,4,5-四嗪-3,6-二羧酸二甲酯
  参考文献：
  名称：

  无铜点击反应序列：一种化学选择性的逐层方法。

  摘要：

  演示了无可点击的双重可点击构建基团的化学选择性连接。平衡反应性和稳定性的挑战是通过使用带有叠氮基团和烯醇醚官能化的环辛炔的小的缺电子的四嗪来实现的。以胆酸衍生的三叠氮化物作为分子表面模型用于逐层合成，证明了应变促进的叠氮化物-炔烃环加成（SPAAC）和反电子需求的Diels-Alder（IEDDA）反应的化学选择性序列。

  DOI：

  10.1021/acs.orglett.9b02891
• 作为产物：
  描述：

  1-乙酰吲哚 、 1,2,4,5-四嗪-3,6-二羧酸二甲酯 以100%的产率得到
  参考文献：
  名称：

  BENSON, SCOTT C.;PALABRICA, CHRISTOPHER A.;SNYDER, JOHN K., J. ORG. CHEM., 52,(1987) N 20, 4610-4614

  摘要：

  DOI：

文献信息

• Synthesis and Characterization of Dialkyl Esters of 1,2,4,5-Tetrazine-3,6-dicarboxylic Acid
  作者：Štěpán Frebort、Numan Almonasy、Radim Hrdina、Antonín Lyčka、Miroslav Lísa、Michal Holčapek

  DOI：10.1135/cccc20080107

  日期：——

  Synthesis and characterization of a series of dialkyl esters of 1,2,4,5-tetrazine-3,6-dicarboxylic acid are reported. These compounds were prepared by a two-stage synthesis: re-esterification of dimethyl 1,4-dihydro-1,2,4,5-tetrazine-3,6-dicarboxylate in the presence of aluminium triethoxide and subsequent dehydrogenation of dialkyl 1,4-dihydro-1,2,4,5-tetrazine-3,6-dicarboxylates. The structures of the prepared compounds were confirmed by NMR and mass spectra.

  报道了一系列1,2,4,5-四氮唑-3,6-二羧酸二烷基酯的合成和表征。这些化合物通过两阶段合成制备：在三乙氧基铝存在下对二甲基1,4-二氢-1,2,4,5-四氮唑-3,6-二羧酸酯进行重新酯化，然后脱氢得到二烷基1,4-二氢-1,2,4,5-四氮唑-3,6-二羧酸酯。通过核磁共振和质谱确认了所制备化合物的结构。
• Synthesis of esters and amides of 1,4-dihydro-1,2,4,5-tetrazine-3,6-dicarboxylic acid
  作者：Shi-Jie Zhang、Yi-Chun Ma、Wei Zhou、Guo-Wu Rao、Liang-Liang Chen、Wei-Xiao Hu

  DOI：10.3184/030823409x12532880130972

  日期：2009.10

  Alkyl esters and alkyl amides of 1,4-dihydro-1,2,4,5-tetrazine-3,6-dicarboxylic acid were synthesised and characterised by IR, 1H NMR, EI-MS and elemental analysis. The structure of 1,4-dihydro-1,2,4,5-tetrazine-3,6-dicarboxylic was confirmed by X-ray diffraction analysis. Some selected compounds were evaluated against P-388 and A-549 cancer cell lines, but showed poor inhibitory activities.

  合成了1,4-二氢-1,2,4,5-四嗪-3,6-二羧酸的烷基酯和烷基酰胺，并通过IR、1H NMR、EI-MS和元素分析对其进行了表征。1,4-二氢-1,2,4,5-四嗪-3,6-二羧酸的结构由X射线衍射分析证实。一些选定的化合物针对 P-388 和 A-549 癌细胞系进行了评估，但显示出较差的抑制活性。
• Dienophilicity of imidazole in inverse electron demand Diels–Alder reactions: cycloadditions with 1,2,4,5-tetrazines and the structure of zarzissine
  作者：Zhao-Kui Wan、Grace H.C. Woo、John K. Snyder

  DOI：10.1016/s0040-4020(01)00476-8

  日期：2001.6

  The inverse electron demand cycloadditions of 2-substituted imidazoles with dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate produced imidazo[4,5-d]pyridazines in good yields. This chemistry was applied to the synthesis of 2-amino-1H-imidazo[4,5-d]pyridazine (1), the structure reported for zarzissine, a cytotoxic marine alkaloid. Differences in the 1H- and 13C NMR spectra of 1 with those reported for zarzissine

  2-取代的咪唑与1,2,4,5-四嗪-3,6-二羧酸二甲酯的反电子需环加成反应可得到高产率的咪唑并[4,5- d ]哒嗪。该化学方法被用于2-氨基-1 H-咪唑并[4,5- d ]哒嗪（1）的合成，该结构报道了具有细胞毒性的海洋生物碱zarzissine的结构。在差异1 H-和13的C NMR光谱1与文献报道为zarzissine必要的结构修改，然后zarzissine被认为是相应的2-氨基-1 ħ -咪唑并[4,5- b ]吡嗪（2），随后由母体杂环合成。
• PROCESS FOR THE COVALENT COUPLING OF TWO MOLECULES BY MEANS OF A DIELS-ALDER REACTION WITH INVERSE ELECTRON REQUIREMENT
  申请人：Wiessler Manfred

  公开号：US20100016545A1

  公开（公告）日：2010-01-21

  The present invention relates to a process for linking two molecules by means of a Diels Alder reaction with inverse electron requirement (DARinv), comprising the following steps: reaction of a (a) triazine or tetrazine with one or more electron-attracting substituents on the ring as a diene component, the electron-attracting substituents being selected from: COOR C(O)NR 2 CX 3 (X=halogen) halogen CN SO 2 —R or SO 3 —R PR 2 wherein R═H, alkyl, aryl, heterocycle, which in turn may be substituted, where appropriate, with alkyl, OH, SH, halogen, aryl, heterocycle, nitro, carboxyamido or amine group. —heterocyclic rings having 1, 2 or 3 N, O or S atoms with a ring size of 5 or 6 ring members, which are substituted with at least one carboxyl, sulfonic acid or phosphone group with (b) an isolated double bond or triple bond in a (hetero)carbocyclic ring or an isolated olefinic double bond or triple bond in a linear or branched hydrocarbon chain which may also contain heteroatoms, where appropriate, as a dienophile component.

  本发明涉及一种利用逆电子需求的Diels-Alder反应（DARinv）将两种分子通过连接的方法，包括以下步骤：将（a）三嗪或四嗪与环上的一个或多个吸电子取代基反应作为二烯组分，所述吸电子取代基被选择自：COOR、C（O）NR2、CX3（X=卤）、卤、CNSO2—R或SO3—RPR2，其中R=H、烷基、芳基、杂环，后者可能被适当地取代，如有必要，可用烷基、OH、SH、卤、芳基、杂环、硝基、羧基氨基或胺基团取代；（b）一种孤立的双键或三键存在于（杂）碳环上，或者一种孤立的烯烃双键或三键存在于线性或支链烃链中，该链也可能含有杂原子，如有必要，作为二烯酰组分。
• Synthesis of <i>N</i>-substituted dibenzoazepine–pyridazine derivatives as potential neurologically active drugs
  作者：Musa Erdoğan、Arif Daştan

  DOI：10.1080/00397911.2020.1828925

  日期：2020.12.16

  Syntheses of pyridazine derivatives of dibenzoazepine, starting from N-substituted-dibenzoazepines, are reported here for the first time. In the reaction sequence, N-substitute dibenzoazepine derivatives were synthesized and then, examined inverse electron demand Diels–Alder (IEDDA) reactions between N-substituted dibenzoazepine derivatives and tetrazines. While in some reactions, targeted products were obtained

  摘要 本文首次报道了以 N-取代的二苯并氮杂为原料合成二苯并氮杂的哒嗪衍生物。在反应序列中，合成了 N-取代的二苯并氮杂衍生物，然后检查了 N-取代的二苯并氮杂衍生物和四嗪之间的逆电子需求 Diels-Alder (IEDDA) 反应。虽然在某些反应中，目标产物是使用苯基碘-双（三氟乙酸盐）（PIFA）获得的，但在其他反应中，它们是直接使用四嗪作为氧化剂获得的。这些化合物的结构通过 NMR、IR 和 HRMS 光谱技术进行了充分表征。图形概要