Phenyl-(α-methylthio)acetaldehyd | 35809-43-9

• 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: Phenyl-(α-methylthio)acetaldehyd
• 英文别名: 2-Methylsulfanyl-2-phenylacetaldehyde
• CAS: 35809-43-9
• 化学式: C₉H₁₀OS
• 分子量: 166.244
• InChiKey: OLBIMKCDKDKKFL-UHFFFAOYSA-N

物化性质

• 沸点：
  232.6±28.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  Phenyl-(α-methylthio)acetaldehyd 在 RhCl(PPh₃)3 作用下， 以 苯 为溶剂， 以60%的产率得到苄基甲基硫醚
  参考文献：
  名称：

  Richardson, Stewart K.; Sabol, Mark R.; Watt, David S., Synthetic Communications, 1989, vol. 19, # 3and4, p. 359 - 368

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(methylsulfinyl)-2-phenylethene 在 五氯化磷 作用下， 生成 Phenyl-(α-methylthio)acetaldehyd
  参考文献：
  名称：

  A Novel Rearrangement of Styryl Sulfoxide Induced by Phosphorus Pentachloride

  摘要：

  两个异构体甲基苯乙烯亚砜（Ia）与该氯化物反应，除了生成β-氯苯乙烯甲基硫化物（IVa）外，还生成甲基苯乙酰硫化物（IIa）和苯基(α-甲基硫)乙醛（IIIa）。苯基苯乙烯亚砜的反应也类似。

  DOI：

  10.1246/bcsj.47.1817

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.
• Duhamel,P. et al., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1972, vol. 274, p. 1233 - 1236
  作者：Duhamel,P. et al.

  DOI：——

  日期：——
• RICHARDSON, STEWART K.;SABOL, MARK R.;WATT, DAVID S., SYNTH. COMMUN., 19,(1989) N-4, C. 359-367
  作者：RICHARDSON, STEWART K.、SABOL, MARK R.、WATT, DAVID S.

  DOI：——

  日期：——
• SHIMAGAKI, MASAYUKI;TAKUBO, HIDEKI;OISHI, TAKESHI, TETRAHEDRON LETT., 1985, 26, N 50, 6235-6238
  作者：SHIMAGAKI, MASAYUKI、TAKUBO, HIDEKI、OISHI, TAKESHI

  DOI：——

  日期：——
• Highly stereoselective reaction ofα-methylthio aldehydes with allyltriphenylstannane: Synthesis of anti-β-methylthio alcohols
  作者：Masayuki Shimagaki、Hideki Takubo、Takeshi Oishi

  DOI：10.1016/s0040-4039(00)95061-5

  日期：1985.1