N,N-dimethyl-1-(methylthio)-3-phenyl-2-propyn-1-amine | 705262-05-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N-dimethyl-1-(methylthio)-3-phenyl-2-propyn-1-amine
• 英文别名: 3-dimethylamino-3-methylthio-1-phenyl-1-propyne；N,N-dimethyl-1-methylsulfanyl-3-phenylprop-2-yn-1-amine
• CAS: 705262-05-1
• 化学式: C₁₂H₁₅NS
• 分子量: 205.324
• InChiKey: BVYLHIGWJZTWHY-UHFFFAOYSA-N

物化性质

• 沸点：
  276.7±35.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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-dimethyl-1-(methylthio)-3-phenyl-2-propyn-1-amine 在 zinc trifluoromethanesulfonate 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以52%的产率得到3-methylsulfanyl-3-phenylprop-2-enal
  参考文献：
  名称：

  乙炔锌与硫亚胺盐的加成反应生成3-氨基-1-亚磺酰基-1,4-烯炔

  摘要：

  硫亚亚胺盐与乙炔锌的反应在60°C进行，以中等至良好的收率得到3-氨基-1-亚磺酰基-1,4-烯炔。将两个乙炔分子掺入产物中。乙炔锌对硫亚胺盐的亲核攻击可能首先发生，形成炔基S，N-乙缩醛，然后进行[1,3]重排，生成3-亚磺基-1-氨基丙烯。

  DOI：

  10.1016/j.tetlet.2005.03.166
• 作为产物：
  描述：

  、 苯乙炔 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 生成 N,N-dimethyl-1-(methylthio)-3-phenyl-2-propyn-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

• Synthesis of Tertiary Propargylamines by Sequential Reactions of in Situ Generated Thioiminium Salts with Organolithium and -magnesium Reagents
  作者：Toshiaki Murai、Yuichiro Mutoh、Yukiyasu Ohta、Masahiro Murakami

  DOI：10.1021/ja048627v

  日期：2004.5.1

  Sequential reactions of thioiminium salts generated from thioamides and methyl triflate with organolithium and -magnesium reagents proceed smoothly to give tertiary propargylamines in moderate to high yields. In all cases, two different organometallic reagents are incorporated into the starting thioamides.

  由硫代酰胺和三氟甲磺酸甲酯生成的硫代亚胺盐与有机锂和镁试剂的连续反应顺利进行，以中等至高产率得到叔炔丙基胺。在所有情况下，两种不同的有机金属试剂都被加入到起始硫代酰胺中。
• 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。
• 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。
• 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.