2-amino-4,5:6,6-bis(tetramethylene)-2,4-cyclohexadiene-1,1,3-tricarbonitrile | 77067-36-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-amino-4,5:6,6-bis(tetramethylene)-2,4-cyclohexadiene-1,1,3-tricarbonitrile
• 英文别名: 3'-amino-5',6',7',8'-tetrahydro-spiro[cyclohexane-1,1'-naphthalene]-2',2',4'-tricarbonitrile；(+/-)-3'-Imino-3'.5'.6'.7'.8'.8a'-hexahydro-2'H-spiro[cyclohexan-1.1'-naphthalin]-tricarbonsaeure-(2'.2'.4')-trinitril；(+/-)-3'-Imino-3'.5'.6'.7'.8'.8a'-hexahydro-2'H-spiro[cyclohexan-1.1'-naphthalin]-tricarbonitril-(2'.2'.4')；3'-Amino-5',6',7',8'-tetrahydro-spiro[cyclohexan-1,1'-naphthalin]-2',2',4'-tricarbonitril；2-Aminospiro[5,6,7,8-tetrahydronaphthalene-4,1'-cyclohexane]-1,3,3-tricarbonitrile
• CAS: 77067-36-8
• 化学式: C₁₈H₂₀N₄
• 分子量: 292.384
• InChiKey: VFDPYAUBPZQNEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  97.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-4,5:6,6-bis(tetramethylene)-2,4-cyclohexadiene-1,1,3-tricarbonitrile 在 盐酸 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 2,4-dicyano-3-oxospiro[6,7,8,8a-tetrahydro-5H-naphthalene-1,1'-cyclohexane]-2-carboxamide
  参考文献：
  名称：

  Syntheses with Unsaturated Nitriles; II. Selective Monoesterification of 2,6,6-Tricyano-2-cyclohexenones by Transannular Rearrangement

  摘要：

  DOI：

  10.1055/s-1980-29270
• 作为产物：
  描述：

  cyano(cyclohexylidene)acetamide 、 丙二腈 在 N-甲基吗啉 作用下， 以 乙醇 为溶剂， 反应 0.33h， 以81%的产率得到2-amino-4,5:6,6-bis(tetramethylene)-2,4-cyclohexadiene-1,1,3-tricarbonitrile
  参考文献：
  名称：

  Synthesis of Substituted 1,3-Cyclohexadienes, Pyridine-2(1H)-thiones, and Thieno[2,3-d]pyrimidine- 4(3H)-thiones by the Michael Reaction

  摘要：

  Cyclopentylidene- and cyclohexylidene(cyano)acetamides reacted with malononitrile and cyano-(thioacetamide) according to the Michael pattern with exchange of the methylene components to give substituted 1-amino-2,6,6-tricyano-1,3-cyclohexadienes and thieno[2,3-d]pyrimidine-4(3H)-thiones. Condensation of cyclopentylidene- and cyclohexylidene(cyano)acetamide with 1,3-dicarbonyl compounds afforded 4,6-dimethyl-3-cyanopyridine-2(1H)-thione and morpholinium 4-methyl-6-oxo-3-cyano-1,6-dihydropyridine-2-thiolate which were converted into substituted 2-alkylsulfanylpyridines, thieno[2,3-b]pyridines, thiazolo[3,2-a]pyridine, and 2H-[1,3]thiazino[3,2-a]pyridine.

  DOI：

  10.1023/b:rujo.0000034978.81993.bd

文献信息

• Syntheses with Unsaturated Nitriles, IX: 3(2H)-Pyridazinones from Alkylidenemalononitrile Dimers
  作者：Maria J. Mokrosz

  DOI：10.1002/ardp.19933260109

  日期：——

  The coupling of 1‐amino‐2,6,6‐tricyanocyclohexadiene derivatives 1‐3 with a variety of aryldiazonium salts produces the hydrazones 5‐7 which in the presence of weak base in ethanol at elevated temperature furnish 2‐aryl‐4‐cyanopyridazin‐3(2H)‐ones 8‐10. In boiling toluene, however, the tautomeric hydrazones 11‐13 are being formed.

  1-氨基-2,6,6-三氰基环己二烯衍生物1-3与各种芳基重氮盐偶联产生腙5-7，在乙醇中弱碱存在下，高温下提供2-芳基-4-氰基哒嗪-3 (2H) -一个 8-10。然而，在沸腾的甲苯中，正在形成互变异构腙11-13。
• ADAMCZYK M.; MIREK J.; MOKROSZ M., SYNTHESIS, 1980, NO 11, 916-918
  作者：ADAMCZYK M.、 MIREK J.、 MOKROSZ M.

  DOI：——

  日期：——
• Syntheses with Unsaturated Nitriles; II. Selective Monoesterification of 2,6,6-Tricyano-2-cyclohexenones by Transannular Rearrangement
  作者：Maciej Adamczyk、Julian Mirek、Maria Mokrosz

  DOI：10.1055/s-1980-29270

  日期：——
• Synthesis of Substituted 1,3-Cyclohexadienes, Pyridine-2(1H)-thiones, and Thieno[2,3-d]pyrimidine- 4(3H)-thiones by the Michael Reaction
  作者：V. D. Dyachenko、A. D. Dyachenko、A. N. Chernega

  DOI：10.1023/b:rujo.0000034978.81993.bd

  日期：2004.3

  Cyclopentylidene- and cyclohexylidene(cyano)acetamides reacted with malononitrile and cyano-(thioacetamide) according to the Michael pattern with exchange of the methylene components to give substituted 1-amino-2,6,6-tricyano-1,3-cyclohexadienes and thieno[2,3-d]pyrimidine-4(3H)-thiones. Condensation of cyclopentylidene- and cyclohexylidene(cyano)acetamide with 1,3-dicarbonyl compounds afforded 4,6-dimethyl-3-cyanopyridine-2(1H)-thione and morpholinium 4-methyl-6-oxo-3-cyano-1,6-dihydropyridine-2-thiolate which were converted into substituted 2-alkylsulfanylpyridines, thieno[2,3-b]pyridines, thiazolo[3,2-a]pyridine, and 2H-[1,3]thiazino[3,2-a]pyridine.