N-methyl-N-(3-phenyl-2-propynyl)-1-naphthalenemethanamine | 98977-91-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-methyl-N-(3-phenyl-2-propynyl)-1-naphthalenemethanamine
• 英文别名: N-methyl-N-(naphthalen-1-ylmethyl)-3-phenylprop-2-yn-1-amine
• CAS: 98977-91-4
• 化学式: C₂₁H₁₉N
• 分子量: 285.389
• InChiKey: IFVMYTMGSKRSLK-UHFFFAOYSA-N

物化性质

• 沸点：
  432.3±28.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于二氯甲烷、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-methyl-N-(3-phenyl-2-propynyl)-1-naphthalenemethanamine 在 Pd-BaSO₄ 氢气 作用下， 以 吡啶 为溶剂， 以44%的产率得到萘替芳Z异构体
  参考文献：
  名称：

  Synthesis and structure-activity relationships of naftifine-related allylamine antimycotics

  摘要：

  Naftifine (1) is the first representative of the new antifungal allylamine derivatives. Its biological activity is strictly bound to specific structural requirements that are unrelated to those of known antifungals. A tertiary allylamine function seems to be a prerequisite for activity against fungi. By systematic variation of the individual structural elements in 1, detailed structure-activity relationships are defined in which the phenyl ring is the structural feature permitting the widest variations. Versatile synthetic routes to allylamine derivatives and comparative biological data are presented.

  DOI：

  10.1021/jm00151a019
• 作为产物：
  描述：

  (氯甲基)萘 在 zinc(II) chloride 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 生成 N-methyl-N-(3-phenyl-2-propynyl)-1-naphthalenemethanamine
  参考文献：
  名称：

  Synthesis and structure-activity relationships of naftifine-related allylamine antimycotics

  摘要：

  Naftifine (1) is the first representative of the new antifungal allylamine derivatives. Its biological activity is strictly bound to specific structural requirements that are unrelated to those of known antifungals. A tertiary allylamine function seems to be a prerequisite for activity against fungi. By systematic variation of the individual structural elements in 1, detailed structure-activity relationships are defined in which the phenyl ring is the structural feature permitting the widest variations. Versatile synthetic routes to allylamine derivatives and comparative biological data are presented.

  DOI：

  10.1021/jm00151a019

文献信息

• Pt(0)-Catalyzed Alkynylation of Aryl Iodides with Lithium Alkynyltriisopropoxy Borates
  作者：Chang Ho Oh、V. Raghava Reddy

  DOI：10.1055/s-2004-832819

  日期：——

  An efficient cross coupling reaction of various lithium alkynyltriiospropoxyborates with a wide array of aryl iodides was catalyzed by Pt(PPh3)4-CuI in DMF as a solvent. These cross coupling reactions are general and permit the new sp-sp2 carbon-carbon bond formation.

  一种高效的交叉耦合反应，将各种锂炔基三异丙苯氧基硼酸酯与多种芳基碘化物在DMF溶剂中，以Pt(PPh3)4-CuI为催化剂进行。这些交叉耦合反应具有普遍性，能够形成新的sp-sp2碳碳键。
• One-Pot Multicomponent Synthesis of Allyl and Alkylamines Using a Catalytic System Composed of Ruthenium Nanoparticles on Copper <i>N</i>-Heterocyclic Carbene-Modified Silica
  作者：Deepti Kalsi、Savarithai J. Louis Anandaraj、Manisha Durai、Claudia Weidenthaler、Meike Emondts、Steven P. Nolan、Alexis Bordet、Walter Leitner

  DOI：10.1021/acscatal.2c04044

  日期：2022.12.16

  integrated one-pot synthesis of valuable allylamines and alkylamines from amines, formaldehyde, and terminal alkynes is achieved using a single catalyst material. This multifunctional catalytic system is composed of a silica support on which are jointly assembled ruthenium nanoparticles and covalently functionalized copper N-heterocyclic carbene (NHC) complexes, introducing a new generation of nanoparticles

  使用单一催化剂材料实现了从胺、甲醛和末端炔烃中一锅法合成有价值的烯丙胺和烷基胺。这种多功能催化系统由二氧化硅载体组成，在其上共同组装了钌纳米粒子和共价功能化的铜N-杂环卡宾 (NHC) 配合物，引入了新一代固定在分子修饰表面上的纳米粒子。通过多种技术研究了所得 Ru@SiO 2 -[Cu-NHC] 材料的结构、结构、形态和电子特性，包括 N 2吸附、固态核磁共振、电子显微镜和 X 射线光电子能谱. Ru@SiO 2-[Cu-NHC] 被发现对一系列烯丙胺和烷基胺的一锅法合成具有活性和选择性，这些产品在精细化工和制药工业中非常重要。详细研究表明，固定化分子 Cu(I)–NHC 络合物负责胺、甲醛和末端炔烃的原子高效 A 3偶联，而所得炔丙基胺的选择性氢化由 Ru(0) 纳米粒子催化. 在单个载体上结合分子和纳米粒子位点的设计策略和制备方法非常灵活，为开发能够在一锅中进行复杂反应序列的多功能催化系统开辟了道路。
• Au(I)-Catalyzed Regioselective Hydrofluorination of Propargylamines Using Aqueous HF
  作者：Hui Yang、Jie Wang、Can Jin、Xiaoqing Li、Xiangsheng Xu

  DOI：10.1021/acs.joc.3c00594

  日期：2023.8.18

  Gold-catalyzed regioselective hydrofluorination of alkynes using aqueous HF has been achieved by employing an amide directing group. For both aryl- and alkyl-substituted propargylamines, the fluorination occurred at the site distal to the amino group.

  通过使用酰胺导向基团，使用 HF 水溶液实现了金催化的炔烃区域选择性氢氟化反应。对于芳基和烷基取代的炔丙胺，氟化发生在氨基远端的位点。
• BERNEY, D.
  作者：BERNEY, D.

  DOI：——

  日期：——
• Synthesis and structure-activity relationships of naftifine-related allylamine antimycotics
  作者：Anton Stuetz、Apostolos Georgopoulos、Waltraud Granitzer、Gabor Petranyi、Daniel Berney

  DOI：10.1021/jm00151a019

  日期：1986.1

  Naftifine (1) is the first representative of the new antifungal allylamine derivatives. Its biological activity is strictly bound to specific structural requirements that are unrelated to those of known antifungals. A tertiary allylamine function seems to be a prerequisite for activity against fungi. By systematic variation of the individual structural elements in 1, detailed structure-activity relationships are defined in which the phenyl ring is the structural feature permitting the widest variations. Versatile synthetic routes to allylamine derivatives and comparative biological data are presented.