ethyl 3-phenyl-2-(phenylthio)propenoate | 82751-37-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl 3-phenyl-2-(phenylthio)propenoate
• 英文别名: ethyl α-phenylthiocinnamate；α-Phenylmercapto-β-phenyl-acrylsaeure-aethylester (cis + trans)；ethyl 3-phenyl-2-phenylsulfanylprop-2-enoate
• CAS: 82751-37-9
• 化学式: C₁₇H₁₆O₂S
• 分子量: 284.379
• InChiKey: NFCMDIXHFOHKOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-phenyl-2-(phenylthio)propenoate 在 磷酸酐 、 氢氧化钾 、 甲烷磺酸 作用下， 以 甲醇 为溶剂， 生成 2-benzylidene-1-benzothiophen-3(2H)-one
  参考文献：
  名称：

  Regiochemical control of the addition of aryl selenols and aryl thiols to the triple bond of arylpropiolates. Synthesis of seleno- and thioflavones and seleno- and thioaurones

  摘要：

  DOI：

  10.1021/jo01311a013
• 作为产物：
  描述：

  苯硫酚 、 苯丙炔酸乙酯 生成 ethyl 3-phenyl-2-(phenylthio)propenoate
  参考文献：
  名称：

  Regiochemical control of the addition of aryl selenols and aryl thiols to the triple bond of arylpropiolates. Synthesis of seleno- and thioflavones and seleno- and thioaurones

  摘要：

  DOI：

  10.1021/jo01311a013

文献信息

• Reaction of 1-Lithio-1-arylthio(or alkylthio)methyltrimethylsilane with Acid Derivatives. A Novel Synthesis of Functionalized Vinyl Sulfides
  作者：Toshio Agawa、Minori Ishikawa、Mitsuo Komatsu、Yoshiki Ohshiro

  DOI：10.1246/bcsj.55.1205

  日期：1982.4

  Reactions of 1-lithio-1-phenylthiomethyl- (1a) and 1-lithio-1-methylthiomethyltrimethylsilane (1b) with amides, an ester, acid anhydrides, a urea, and a carbonate are described which provide useful routes to functionalized vinyl sulfides. The reaction of 1 with amides gave β-functionalized vinyl sulfides, 1-dialkylamino-2-phenylthio (or methylthio)ethylenes, in 40–95% yields and the reaction could

  描述了 1-锂硫基-1-苯硫基甲基-(1a) 和 1-锂硫基-1-甲硫基甲基三甲基硅烷 (1b) 与酰胺、酯、酸酐、脲和碳酸酯的反应，它们提供了用于官能化乙烯基硫化物的有用途径。1 与酰胺反应得到 β-官能化乙烯基硫化物，1-二烷基氨基-2-苯硫基（或甲硫基）乙烯，产率 40-95%，反应可以扩展到 1 的磺酰基衍生物，得到 1-二烷基氨基- 2-苯基磺酰基（或甲基磺酰基）乙烯。尽管苯甲酸乙酯和一些酸酐不是该反应的良好底物，但四甲基脲和碳酸二乙酯在用 1a 处理后以中等产率生成 α-官能化乙烯基硫化物、1-酰胺乙烯基和 1-（乙氧基羰基）乙烯基硫化物，然后加入苯甲醛。
• Microwave-Assisted Tandem Nucleophilic Substitution-Wittig Reaction of α<i>-</i>Hypervalent Iodine Functionalized Phosphonium Ylide
  作者：Xian Huang、Xiaochun Yu

  DOI：10.1055/s-2002-34893

  日期：——

  Under microwave irradiation conditions the tandem nucleophilic substitution-Wittig reaction of α-hypervalent iodine functionalized phosphonium ylide can occur readily to afford α-heteroatom substituted-α,β-unsaturated enoates in good yields stereoselectively.

  在微波辐照条件下，δ-高价碘官能化膦酰亚胺很容易发生串联亲核取代-维蒂希反应，从而以良好的收率立体选择性地获得δ-杂原子取代的δ,δ-不饱和烯酸盐。
• Synthesis of 1-Amino-2-naphthalenecarboxylic Acid Derivatives via the Intramolecular Cyclization of 4-(2-Cyanophenyl)-2-butenoic Acid Derivatives and Its Application to the One-Pot Preparation of Benzo[<i>h</i>]quinazoline-2,4(1<i>H</i>,3<i>H</i>)-diones
  作者：Kazuhiro Kobayashi、Hiroto Tanaka、Harumi Takabatake、Tomohide Kitamura、Ryoji Nakahashi、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.1246/bcsj.72.1071

  日期：1999.5

  The reaction of 2-(lithiomethyl)benzonitrile with 2-phenylthio-2-alkenoic acid derivatives in diglyme at −78 °C, followed by oxidation with sodium metaperiodate in aqueous MeOH at room temperature and the subsequent elimination reaction in refluxing toluene, gave 4-(2-cyanophenyl)-2-butenoic acid derivatives in moderate-to-fair overall yields. Intramolecular cyclization of these products using NaH in DMF at 0 °C gave 1-amino-2-naphthalenecarboxylic acid derivatives almost quantitatively. Successive treatments with an isocyanate without isolation of the aminonaphthalenecarboxylates under reflux afforded benzo[h]quinazoline-2,4(1H,3H)-diones in moderate-to-good yields.

  2- (lithiomethyl)苯甲腈与 2-苯硫基-2-烯酸衍生物在-78 °C的二甘醇中反应，然后在室温下用偏碘酸钠在水性 MeOH 中氧化，随后在回流甲苯中进行消去反应，得到 4-(2-氰基苯基)-2-丁烯酸衍生物，总产率中等至一般。在 0 °C 的 DMF 中使用 NaH 对这些产物进行分子内环化，几乎定量地得到了 1-氨基-2-萘甲酸衍生物。在不分离氨基萘甲酸酯的情况下，用异氰酸酯在回流条件下连续处理，可得到苯并[h]喹唑啉-2,4(1H,3H)-二酮，收率为中等至良好。
• Regiochemical control of the addition of aryl selenols and aryl thiols to the triple bond of arylpropiolates. Synthesis of seleno- and thioflavones and seleno- and thioaurones
  作者：Donald H. Wadsworth、Michael R. Detty

  DOI：10.1021/jo01311a013

  日期：1980.11