(E)-N-methyl-N-(naphthalen-1-ylmethyl)-5-(trimethylsilyl)pent-2-en-4-yn-1-amine | 84213-96-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-N-methyl-N-(naphthalen-1-ylmethyl)-5-(trimethylsilyl)pent-2-en-4-yn-1-amine
• 英文别名: trans-N-(1-naphthylmethyl)-N-methyl-5-trimethylsilyl-pent-2-en-4-ynyl-1-amine；(E)-N-methyl-N-(naphthalen-1-ylmethyl)-5-trimethylsilylpent-2-en-4-yn-1-amine
• CAS: 84213-96-7
• 化学式: C₂₀H₂₅NSi
• 分子量: 307.511
• InChiKey: OUFCFBDEQVYPJU-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  trans N-methyl-N-(1-naphthylmethyl)pent-2-en-4-ynyl-1-amine 在 正丁基锂 、 三甲基氯硅烷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 (E)-N-methyl-N-(naphthalen-1-ylmethyl)-5-(trimethylsilyl)pent-2-en-4-yn-1-amine
  参考文献：
  名称：

  Silyl-alkyn-en-ylamine derivatives

  摘要：

  具有药用特性，特别是抗真菌活性的硅基-炔基-烯基胺衍生物。

  公开号：

  US04542022A1

文献信息

• A two-step synthesis of terbinafine
  作者：Mouâd Alami、Fabiola Ferri、Yann Gaslain

  DOI：10.1016/0040-4039(95)02095-0

  日期：1996.1

  An efficient and high yielding synthesis of terbinafine 1a and amino enyne derivatives 1b-f is described from amino vinyl chlorides 2a-b and 1-alkynes in the presence of a weak ligated palladium complex: PdCl2(PhCN)2 in piperidine.

  描述了在弱连接的钯络合物：PdCl 2（PhCN）2在哌啶中的存在下，由氨基氯乙烯2a-b和1-炔烃有效高效地合成特比萘芬1a和氨基烯炔衍生物1b-f的方法。
• Synthesis of terbinafine. A palladium catalyzed vinyl iodide-ethynylstannane coupling
  作者：Duane E. Rudisill、Laurie A. Castonguay、J.K. Stille

  DOI：10.1016/s0040-4039(00)80338-x

  日期：——
• STUETZ, A.
  作者：STUETZ, A.

  DOI：——

  日期：——
• Accessing Z‐Enynes via Cobalt‐Catalyzed Propargylic Dehydrogenation
  作者：Alexandra K. Bodnar、Timothy R. Newhouse

  DOI：10.1002/anie.202402638

  日期：——

  Alkenes constitute an enabling motif in organic synthesis, as they can be functionalized to form highly substituted molecules. Z‐alkenes are generally challenging to access due to the thermodynamic preference for the formation of E‐alkenes compared to Z‐alkenes. Dehydrogenation methodologies to selectively form Z‐alkenes have not yet been reported. Herein, we report a Z‐selective, propargylic dehydrogenation that provides 1,3‐enynes through the invention of a Co‐catalyzed oxidation system. Observation of a kinetic isotope effect (KIE) revealed that deprotonation of the propargylic position is the rate limiting step. Additionally, isomerization experiments were conducted and confirmed that the observed Z‐selectivity is a kinetic effect. A proposed stereomechanistic model for the Z‐selectivity is included.
• Silyl-alkyn-en-ylamine derivatives
  申请人：Sandoz Ltd.

  公开号：US04542022A1

  公开（公告）日：1985-09-17

  Silyl-alkyn-en-ylamine derivatives which possess pharmaceutical in particular anti-mycotic activity.

  具有药用特性，特别是抗真菌活性的硅基-炔基-烯基胺衍生物。