N,N,4-trimethyl-1-(methylthio)-4-penten-2-yn-1-amine

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫半缩醛胺衍生物
• 英文名称: N,N,4-trimethyl-1-(methylthio)-4-penten-2-yn-1-amine
• 英文别名: 5-dimethylamino-5-methylthio-2-methyl-1-penten-3-yne；N,N,4-trimethyl-1-methylsulfanylpent-4-en-2-yn-1-amine
• 化学式: C₉H₁₅NS
• 分子量: 169.291
• InChiKey: XEOQGKSZDRCQRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  28.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N,4-trimethyl-1-(methylthio)-4-penten-2-yn-1-amine 、 三氟甲烷磺酸甲酯 以 乙醚 为溶剂， 反应 0.08h， 生成 trimethyl-N-(1-methylsulfanyl-1-(3-methyl-3-buten-1-ynyl))methylammonium trifluoromethanesulfonate
  参考文献：
  名称：

  1-甲基硫代炔丙基铵盐的合成和性质及其作为含硫烯二炔的关键前体的用途。

  摘要：

  通过炔基S，N-乙缩醛与三氟甲磺酸甲酯的反应以高效方式合成了1-甲硫基炔丙基铵盐。1-甲基硫代炔丙基铵盐与格利雅试剂的反应产生炔丙基硫化物或烯丙基硫，而与有机铜试剂的反应导致炔丙基硫化物的排他性形成，而与炔碳上取代基的性质无关。当用有机锂和酰胺化锂碱处理时，这些盐会发生自二聚反应。

  DOI：

  10.1021/ol7024923
• 作为产物：
  描述：

  、 2-甲基-1-丁烯-3-炔 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 以96%的产率得到N,N,4-trimethyl-1-(methylthio)-4-penten-2-yn-1-amine
  参考文献：
  名称：

  Syntheses and Stability of Alkynyl S,N-Acetals Derived from 2-Propynals

  摘要：

  Two types of synthetic methods for S, N-acetals derived from 2-propynals were described. Thioformamides, lithium acetylides, and alkylating agents were the key substrates. In the first method, methylation of thioformamides with MeOTf followed by reacting with lithium acetylides led to the title compounds. As an alternative method, the direct addition of lithium acetylides to thioformamides gave lithium thiolates, which was then alkylated. With these two methods, a wide range of derivatives including bis-S, N-acetals were provided, and their stability was influenced by the substituents at the alkynyl carbon atom. The introduction of silyl group enhanced the stability effectively.

  DOI：

  10.1080/10426500902947765

文献信息

• Alkynyl S, N-acetal derivative and method of producing the same
  申请人：Gifu University

  公开号：US20040167346A1

  公开（公告）日：2004-08-26

  An alkynyl S,N-acetal derivative of the present invention is represented by the following structural formula: 1 In the structural formula, R 1 represents a hydrogen atom, an alkyl group, an aryl group, an alkenyl group, a silyl group, or an alkynyl group; each of R 2 and R 3 represents an alkyl group or an allyl group; and R 4 represents an alkyl group. The alkynyl S,N-acetal derivative, which is a novel compound, is useful as a raw material of propargylamine.

  本发明的炔基S，N-缩醛衍生物由以下结构式表示： 1 在结构式中，R 1 代表氢原子，烷基，芳基，烯基，硅基或炔基中的一个；R 2 和R 3 中的每一个代表烷基或烯丙基；R 4 代表烷基。这种炔基S，N-缩醛衍生物是一种新颖的化合物，可用作丙炔胺的原料。
• US6958419B2
  申请人：——

  公开号：US6958419B2

  公开（公告）日：2005-10-25
• Syntheses and Stability of Alkynyl <i>S,N</i>-Acetals Derived from 2-Propynals
  作者：Toshiaki Murai、Kozue Fukushima、Yukiyasu Ohta、Yuichiro Mutoh

  DOI：10.1080/10426500902947765

  日期：2009.6.23

  Two types of synthetic methods for S, N-acetals derived from 2-propynals were described. Thioformamides, lithium acetylides, and alkylating agents were the key substrates. In the first method, methylation of thioformamides with MeOTf followed by reacting with lithium acetylides led to the title compounds. As an alternative method, the direct addition of lithium acetylides to thioformamides gave lithium thiolates, which was then alkylated. With these two methods, a wide range of derivatives including bis-S, N-acetals were provided, and their stability was influenced by the substituents at the alkynyl carbon atom. The introduction of silyl group enhanced the stability effectively.
• Synthesis and Properties of 1-Methylthiopropargylammonium Salts and Their Use as Key Precursors to Sulfur-Containing Enediynes
  作者：Toshiaki Murai、Kozue Fukushima、Yuichiro Mutoh

  DOI：10.1021/ol7024923

  日期：2007.12.1

  N-acetals with methyl triflate. Reactions of the 1-methylthiopropargylammonium salts with Grignard reagents gave propargyl sulfides or allenyl sulfides, whereas the reaction with organocopper reagents led to exclusive formation of allenyl sulfides regardless of the nature of substituents on the acetylenic carbon. The salts undergo self-dimerization reactions when treated with organolithium and lithium

  通过炔基S，N-乙缩醛与三氟甲磺酸甲酯的反应以高效方式合成了1-甲硫基炔丙基铵盐。1-甲基硫代炔丙基铵盐与格利雅试剂的反应产生炔丙基硫化物或烯丙基硫，而与有机铜试剂的反应导致炔丙基硫化物的排他性形成，而与炔碳上取代基的性质无关。当用有机锂和酰胺化锂碱处理时，这些盐会发生自二聚反应。