α-methylmercaptopropionamidine | 13382-53-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: α-methylmercaptopropionamidine
• 英文别名: (methylthio)propanal；2-methylsulfanyl-propionaldehyde；2-Methylmercapto-propionaldehyd；2-Methylmercapto-propionaldehyde；2-methylsulfanylpropanal
• CAS: 13382-53-1
• 化学式: C₄H₈OS
• 分子量: 104.173
• InChiKey: DNOUKPGPAUUCPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  α-methylmercaptopropionamidine 在 硫酸 作用下， 生成 1-甲基硫代-2-丙酮
  参考文献：
  名称：

  Kirrmann,A. et al., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1962, vol. 255, p. 728 - 730

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯丙醛 、 sodium thiomethoxide 生成 α-methylmercaptopropionamidine
  参考文献：
  名称：

  Kirrmann,A. et al., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1962, vol. 255, p. 728 - 730

  摘要：

  DOI：

文献信息

• Diastereoselection during 1,2-Addition of the Allylindium Reagent to α-Thia and α-Amino Aldehydes in Aqueous and Organic Solvents
  作者：Leo A. Paquette、Thomas M. Mitzel、Methvin B. Isaac、Curtis F. Crasto、William W. Schomer

  DOI：10.1021/jo970274d

  日期：1997.6.1

  The stereochemistry of the indium-promoted reaction of allyl bromide with alpha-thia (PhS and MeS), disubstituted alpha-amino (Bn2N, Me2N, isoindolyl), and protected alpha-amino aldehydes (Ac and Boc) in water has been evaluated. The reactions involving the sulfur derivatives are minimally diastereoselective, indicating that the allylindium reagent is not thiophilic. Chelation is not observed and pi-facial discrimination is achieved via Felkin-Ahn transition states under the steric control of the substituents. The Garner aldehyde is also anti-diastereoselective. Interestingly, N-acetylmannosamine is appreciably responsive to chelation control and is capable of generating 90% of the syn beta-amino alcohol when reacted in a 0.5 M NH4Cl solution. While the alpha-dibenzylamino substituent is too bulky to enter into complexation, the alpha-dimethylamino group is not and can lead to high levels (99%) of syn diastereomer. The size of other neighboring substituents does have an impact on pi-facial discrimination in these systems and can erode the stereoselectivity accordingly.
• Kirrmann,A. et al., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1962, vol. 255, p. 728 - 730
  作者：Kirrmann,A. et al.

  DOI：——

  日期：——