N-methyl-N-(prop-2-ynyl)naphthalen-1-amine | 40174-31-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-methyl-N-(prop-2-ynyl)naphthalen-1-amine
• 英文别名: N-methyl-N-(2-propynyl)-1-naphthylamine；N-methyl-N-propargyl-1-aminonaphthalene；N-Methyl-N-propargyl-1-naphthylamin；N-methyl-N-prop-2-ynylnaphthalen-1-amine
• CAS: 40174-31-0
• 化学式: C₁₄H₁₃N
• 分子量: 195.264
• InChiKey: CUOWXNTTYNMACZ-UHFFFAOYSA-N

物化性质

• 沸点：
  301.8±25.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3,4-二异丙氧基-3-环丁烯-1,2-二酮 、 N-methyl-N-(prop-2-ynyl)naphthalen-1-amine 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到2,3-diisopropoxy-4-hydroxy-4-[3-[N-methyl-N-(1-naphthyl)amino]-1-propynyl]-2-cyclobuten-1-one
  参考文献：
  名称：

  Rearrangements of Cyclobutenones. Synthesis of N-Methyl-7,8-dihydrobenzophenanthridine-9,12-diols and Related Compounds

  摘要：

  A useful synthetic route to benzophenanthridines and annulated derivatives is reported. These arise from the thermolysis (refluxing chlorobenzene) of squaric acid-derived C(3-N-methyl-N-arylpropynyl)-cyclobutenones via a mechanism which involves an electrocyclic ring opening of the cyclobutenone to the corresponding enynylketenes. Subsequent ring closure to a diradical intermediate followed by radical arylation gives the benzophenanthridines.

  DOI：

  10.1021/jo990505b
• 作为产物：
  描述：

  N-propargyl-1-naphthylamine 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以75%的产率得到N-methyl-N-(prop-2-ynyl)naphthalen-1-amine
  参考文献：
  名称：

  铑（II）催化环状合成取代的3-吲哚基亚胺和吲哚-3-甲醛

  摘要：

  提出了一种有效的Cu / Rh催化方法，该方法通过Rh（II）催化的N-磺酰基-1,2,3-三唑的脱氮环化反应，由N-炔丙基苯胺合成3-吲哚基亚胺。进一步与水解或还原相结合，开发了一种一锅法，可将亚胺，醛或胺基团直接从炔烃引入吲哚体系。以高收率合成了多种取代的3-吲哚基亚胺，吲哚-3-羧醛和3-吲哚基甲胺。

  DOI：

  10.1021/ol501618z

文献信息

• Copper catalysed alkynylation of tertiary amines with CaC₂via sp³ C–H activation
  作者：Siew Ping Teong、Dingyi Yu、Yin Ngai Sum、Yugen Zhang

  DOI：10.1039/c6gc00872k

  日期：——

  A mild and easy-to-handle protocol to produce propargylamines with a terminal alkyne through sp³ C–H bond activation and C–C coupling of tertiary amines and calcium carbide has been developed.

  一个温和且易于操作的协议，通过sp³ C–H键活化和三级胺与钙 carbide的C–C偶联生产带有端炔的炔丙胺已经开发出来。
• Ring Expansion of 4-Alkynylcyclobutenones. Synthesis of Piperidinoquinones, Highly Substituted Dihydrophenanthridines, Benzophenanthridines, and the Naturally Occurring Pyrrolophenanthridine, Assoanine
  作者：Yifeng Xiong、Harold W. Moore

  DOI：10.1021/jo9613803

  日期：1996.1.1

  New synthetic routes to a variety of N-heterocyclic quinones and hydroquinones are described. These include thermolyses of 4-hydroxy-4-[4-N-(benzenesulfonyl)-4-aza-1,6-dialkynyl]cyclobutenones to piperidinoquinones and 4-hydroxy-4-[3-(N-phenylamino)-1-propynyl] cyclobutenones to dihydrophenanthridinediols. Included in the array of products available by this method are benzophenanthridines, indolophenanthridines, isoindoloindoles, and pyrrolophenanthridines. The methodology was employed in a five-step synthesis of the alkaloid assoanine starting with dimethyl squarate and indoline. The key step in all of these transformations is the ring expansion of appropriately substituted 4-hydroxy-4-alkynylcyclobutenones. These are envisaged to undergo electrocyclic ring opening to the corresponding enynylketenes which ring close to diradical intermediates that then lead to products via either radical additions to proximal alkyne moieties or undergo homolytic aromatic substitution to appropriately placed aryl groups. The synthetic scope and mechanism of the ring expansion reactions are discussed.