(E)-1-Methoxy-2-phenyl-1-(phenylthio)ethene | 88738-26-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (E)-1-Methoxy-2-phenyl-1-(phenylthio)ethene
• 英文别名: [(E)-2-methoxy-2-phenylsulfanylethenyl]benzene；[(E)-1-methoxy-2-phenylethenyl]sulfanylbenzene
• CAS: 88738-26-5
• 化学式: C₁₅H₁₄OS
• 分子量: 242.342
• InChiKey: FASQDPCGYPJQJH-NTCAYCPXSA-N

物化性质

• 沸点：
  370.6±42.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-Methoxy-2-phenyl-1-(phenylthio)ethene 在 溶剂黄146 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 36.53h， 生成 phenylacetylpyrrolidine
  参考文献：
  名称：

  [Methoxy(phenylthio)methyl]lithium and [methoxy(phenylthio)(trimethylsilyl)methyl]lithium. Two exceedingly convenient reagents for the facile conversion of aldehydes, ketones, and 3-alkoxy enones into ketene O,S-acetal derivatives

  摘要：

  DOI：

  10.1021/jo00356a025
• 作为产物：
  描述：

  甲氧基甲基苯硫醚 在 1,10-菲罗啉 、 四甲基乙二胺 、 仲丁基锂 作用下， 反应 4.25h， 生成 (E)-1-Methoxy-2-phenyl-1-(phenylthio)ethene
  参考文献：
  名称：

  [Methoxy(phenylthio)methyl]lithium and [methoxy(phenylthio)(trimethylsilyl)methyl]lithium. Two exceedingly convenient reagents for the facile conversion of aldehydes, ketones, and 3-alkoxy enones into ketene O,S-acetal derivatives

  摘要：

  DOI：

  10.1021/jo00356a025

文献信息

• Asymmetric Nucleophilic Acylation of Aldehydes via 1,1-Heterodisubstituted Alkenes
  作者：Holger Monenschein、Gerald Dräger、Alexander Jung、Andreas Kirschning

  DOI：10.1002/(sici)1521-3765(19990802)5:8<2270::aid-chem2270>3.0.co;2-l

  日期：1999.8.2

  Aldehydes are asymmetrically acylated by a two step sequence that is initiated by a homologation step to 1,1-heterodisubstituted alkenes followed by asymmetric dihydroxylation. Thus, ketene O,S-acetals are efficiently prepared from aldehydes by a Peterson olefination with lithiated methoxy-phenylthiotrimethylsilyl methane 14 as the C-1 source. Although they are dihydroxylated with the Sharpless catalyst with moderate to good enantioselectivity (62-80% ee), the process is not efficient owing to the low chemical yields of the desired alpha-hydroxy methyl esters (7-37%). Use of the corresponding sulfoxide 24 or sulfon 25 led to an improved chemical yield of alpha-hydroxy methyl ester 19, but the stereoselectivity was diminished. In contrast, intermediate ketene O,O-acetals are prepared by a Horner-Wittig reaction with phosphine oxide 31 and are dihydroxylated both with good chemical and stereochemical yield. The concept is applicable to aromatic, aliphatic, and chiral aldehydes. For example, this short sequence allows exclusive and independent preparation of both diastereomeric heptoses 69a and 69b.
• A new version of the Peterson olefination using bis(trimethylsilyl)methyl derivatives and fluoride ion as catalyst
  作者：Claudio Palomo、Jesus M. Aizpurua、Jesus M. Garcia、Inaki Ganboa、F. P. Cossio、Begona Lecea、Concepcion Lopez

  DOI：10.1021/jo00295a047

  日期：1990.4
• PALOMO, CLAUDIO;AIZPURUA, JESUS M.;GARCIA, JESUS M.;GANBOA, INAKI;COSSIO,+, J. ORG. CHEM., 55,(1990) N, C. 2498-2503
  作者：PALOMO, CLAUDIO、AIZPURUA, JESUS M.、GARCIA, JESUS M.、GANBOA, INAKI、COSSIO,+

  DOI：——

  日期：——
• DE, GROOT, A.;JANSEN, B. J. M., SYNTH. COMMUN., 1983, 13, N 12, 985-990
  作者：DE, GROOT, A.、JANSEN, B. J. M.

  DOI：——

  日期：——
• HACKETT, ST.;LIVINGHOUSE, T., J. ORG. CHEM., 1986, 51, N 6, 879-885
  作者：HACKETT, ST.、LIVINGHOUSE, T.

  DOI：——

  日期：——