(E,E)-1-(N,N-dimethylamino)-4-nitro-1,3-butadiene | 108030-46-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (E,E)-1-(N,N-dimethylamino)-4-nitro-1,3-butadiene
• 英文别名: 1-(N,N-dimethylamino)-4-nitro-1,3-butadiene；1-(N,N-dimethylamino)-4-nitro-1,3-butadine；tert-nitrodienamine；(1E,3E)-N,N-dimethyl-4-nitrobuta-1,3-dien-1-amine
• CAS: 108030-46-2
• 化学式: C₆H₁₀N₂O₂
• 分子量: 142.158
• InChiKey: FZNPOSVPEAZERM-GGWOSOGESA-N

物化性质

• 沸点：
  216.4±23.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  吲哚-3-乙腈 、 (E,E)-1-(N,N-dimethylamino)-4-nitro-1,3-butadiene 在 乙基溴化镁 作用下， 生成 1-[1-(3-cyanomethylindolyl)]-4-nitro-1,3-butadiene
  参考文献：
  名称：

  Condensation Reactions of a Nitrodienamine with Grignard Reagents Prepared from Phenyl Bromide, Bromotoluene, Indoles, and Carbazole

  摘要：

  Condensation reactions of a nitrodienamine (1) with Grignard reagents prepared from phenyl bromide, 4-bromotoluene, indole (6a), 3-methylindole (6b), 2,3-dimethylindole (6c), 3-cyanomethylindole (6d), and carbazole (6e) were investigated.

  DOI：

  10.3987/com-97-7787
• 作为产物：
  描述：

  硝基甲烷 、 3-dimethylaminopropenylidenedimethylammonium chloride 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到(E,E)-1-(N,N-dimethylamino)-4-nitro-1,3-butadiene
  参考文献：
  名称：

  Takeuchi, Naoki; Ohki, Junji; Tobinaga, Seisho, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 2, p. 481 - 487

  摘要：

  DOI：

文献信息

• A New Synthesis of Indoloquinolizines by Pictet-Spengler Reaction of Tryptamine Type 1,2-Dihydropyridines Utilizing sec-Nitrodienamine.
  作者：Takeshi KOIKE、Yoshifumi SHINOHARA、Seisho TOBINAGA、Naoki TAKEUCHI

  DOI：10.1248/cpb.48.1898

  日期：——

  The Pictet-Spengler reaction of tryptamine type 1, 2-dihydropyridine 5c derived from the cycloaddition of the sec-nitrodienamine 3c with acetaldehyde afforded the indoloquinolizine derivatives 6 and 7.

  色胺的Pictet-Spengler反应，2,3-二氢吡啶5c源自sec-硝基二烯胺3c与乙醛的环加成反应，生成了吲哚喹啉杂环衍生物6和7。
• A New and Efficient Synthesis of 2-Methyl-3-nitro-1,2-dihydropyridines by Heterocyclic Annulation Reactions of sec-Nitrodienamines with Acetaldehyde.
  作者：Takeshi KOIKE、Yoshifumi SHINOHARA、Mituharu TANABE、Naoki TAKEUCHI、Seisho TOBINAGA

  DOI：10.1248/cpb.47.1246

  日期：——

  The sec-nitrodienamines 3 were prepared by reaction of the tert-nitrodienamine 1 with primary amines. The reaction of 3 with acetaldehyde afforded 2-methyl-3-nitro-1, 2-dihydropyridines 5, providing a new and efficient heterocyclic annulation reaction.

  仲硝基二烯胺 3 是通过叔硝基二烯胺 1 与伯胺反应制备的。3 与乙醛反应生成 2-甲基-3-硝基-1, 2-二氢吡啶 5，提供了一种新的高效杂环环化反应。
• Synthesis of 2-Substituted 3-Nitro-1,2-dihydropyridines by Heterocyclic Annulation reactions of a sec-Nitrodienamine with Aldehyde Compounds.
  作者：Takeshi KOIKE、Yoshifumi SHINOHARA、Noriko ISHIBASHI、Naoki TAKEUCHI、Seisho TOBINAGA

  DOI：10.1248/cpb.48.436

  日期：——

  The reaction of a sec-nitrodienamine 3 with aldehyde compounds afforded 2-substituted 3-nitro-1,2-dihydropyridines 5, providing a heterocyclic annulation reaction.

  仲硝基二胺3与醛化合物的反应得到2-取代的3-硝基-1,2-二氢吡啶5，提供了杂环环化反应。
• Condensation Reactions of a Nitrodienamine with Organocopper and Alkyllithium Reagents Prepared from Pyrrole Derivatives
  作者：Takeshi Koike、Yoshifumi Shinohara、Takeshi Nishimura、Masanori Hagiwara、Seisho Tobinaga、Naoki Takeuchi

  DOI：10.3987/com-00-8859

  日期：——

  Condensation reactions of a nitrodienamine (1) with Grignard, organocopper and alkyllithium reagents prepared from pyrrole derivatives were investigated.
• Condensation Reactions of a Nitrodienamine with Grignard and Organocopper Reagents Prepared from Indole Derivatives
  作者：Takeshi Koike、Naoki Takeuchi、Masanori Hagiwara、Kaori Yamazaki、Seisho Tobinaga

  DOI：10.3987/com-99-8684

  日期：——

  Condensation reactions of a nitrodienamine (1) with Grignard and organocopper reagents prepared from indole derivatives were investigated. Indolyl Grignard reagents were prepared from 4-bromoindole (3a), 5-bromoindole (3b), 6-bromoindole (3c), and 5-nitroindole (3d) using methylmagnesium bromide. Indolyl organocopper reagents were prepared from indole (3e), 2-methylindole (3f), and 3-methylindole (3g) using dimethylcopperlithium.