3-Phenyl-thioprop-2-ensaeure-S-methylester | 15081-18-2

• 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: 3-Phenyl-thioprop-2-ensaeure-S-methylester
• 英文别名: S-methyl thiocinnamate；S-methyl 3-phenylprop-2-enethioate
• CAS: 15081-18-2
• 化学式: C₁₀H₁₀OS
• 分子量: 178.255
• InChiKey: PFCNRGCTEUBSML-UHFFFAOYSA-N

物化性质

• 熔点：
  48.5-49 °C
• 沸点：
  315.3±12.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  3-Phenyl-thioprop-2-ensaeure-S-methylester 、 B-溴代邻苯二氧硼烷 以 二氯甲烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Stereoselective Synthesis of Novel Diels–Alder Adducts of p-Substituted Methyl Thiocinnamates and Cyclopentadiene

  摘要：

  This article describes the Diels-Alder reaction between methyl thiocinnamates, substituted at the para position by electron-donating and electron-withdrawing groups, with cyclopentadiene in the presence of catechol boron bromide (CBB) as a Lewis acid catalyst. The adduct configuration was confirmed by H-1 NMR coupling constants and single-crystal x-ray diffraction. Total endo stereoselectivity was observed in all reactions and was attributed to the effective secondary interaction between the boron atom and the incipient double bond in the norbonene resulting from the planar geometry of the catalyst. C-13 NMR chemical shifts of the coordinated dienophile carbonyl carbons with CBB compared to those of the non coordinated thiocinammates suggest a strong complexation with the catalyst.

  DOI：

  10.1080/00397911.2010.524962
• 作为产物：
  描述：

  3,3-双甲基磺酰基-1-苯丙酮 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 生成 3-Phenyl-thioprop-2-ensaeure-S-methylester
  参考文献：
  名称：

  Saquet,M.; Thuillier,A., Bulletin de la Societe Chimique de France, 1966, p. 3969 - 3977

  摘要：

  DOI：

文献信息

• Direct Catalytic Asymmetric Vinylogous Conjugate Addition of Unsaturated Butyrolactones to α,β-Unsaturated Thioamides
  作者：Liang Yin、Hisashi Takada、Shaoquan Lin、Naoya Kumagai、Masakatsu Shibasaki

  DOI：10.1002/anie.201402332

  日期：2014.5.19

  Soft Lewis acid/Brønsted base cooperative catalysts have enabled direct catalytic asymmetric vinylogous conjugate addition of α,β‐ and β,γ‐unsaturated butyrolactones to α,β‐unsaturated thioamides with perfect atom economy. When using α‐angelica lactone and its derivatives as pronucleophiles, as little as 0.5 mol % catalyst loading was sufficient to complete the reaction necessary to construct consecutive

  软路易斯酸/布朗斯台德碱协同催化剂已使α，β-和β，γ-不饱和丁内酯直接催化不对称乙烯基共轭加成到α，β-不饱和硫代酰胺中，具有完美的原子经济性。当使用α-当归内酯及其衍生物作为亲核试剂时，低至0.5 mol％的催化剂负载量足以完成以高度非对映和对映选择性的方式构建连续的三和四取代的立体异构中心所必需的反应。
• Cytochalasin support studies. 10. Nucleophilic and electrophilic mercaptanylations via 2-(trimethylsilyl)ethanethiol-derived reagents
  作者：M. B. Anderson、M. G. Ranasinghe、J. T. Palmer、P. L. Fuchs

  DOI：10.1021/jo00248a045

  日期：1988.6
• Saquet,M.; Thuillier,A., Bulletin de la Societe Chimique de France, 1966, p. 3969 - 3977
  作者：Saquet,M.、Thuillier,A.

  DOI：——

  日期：——
• Stereoselective Synthesis of Novel Diels–Alder Adducts of <i>p</i>-Substituted Methyl Thiocinnamates and Cyclopentadiene
  作者：Fernanda F. Camilo、Jonas Gruber

  DOI：10.1080/00397911.2010.524962

  日期：2012.2.1

  This article describes the Diels-Alder reaction between methyl thiocinnamates, substituted at the para position by electron-donating and electron-withdrawing groups, with cyclopentadiene in the presence of catechol boron bromide (CBB) as a Lewis acid catalyst. The adduct configuration was confirmed by H-1 NMR coupling constants and single-crystal x-ray diffraction. Total endo stereoselectivity was observed in all reactions and was attributed to the effective secondary interaction between the boron atom and the incipient double bond in the norbonene resulting from the planar geometry of the catalyst. C-13 NMR chemical shifts of the coordinated dienophile carbonyl carbons with CBB compared to those of the non coordinated thiocinammates suggest a strong complexation with the catalyst.