Zimtsaeure-thioethylester | 42893-53-8

• 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: Zimtsaeure-thioethylester
• 英文别名: S-ethyl 3-phenylprop-2-enethioate
• CAS: 42893-53-8
• 化学式: C₁₁H₁₂OS
• 分子量: 192.282
• InChiKey: HIXVHZUGIFAYNP-UHFFFAOYSA-N

物化性质

• 沸点：
  150-152 °C(Press: 11 Torr)
• 密度：
  1.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  Zimtsaeure-thioethylester 在 copper acetate monohydrate 、 1,2-双(二苯基膦基)苯 、 叔丁醇 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以90%的产率得到S-ethyl 3-phenylpropanethioate
  参考文献：
  名称：

  Conjugate reduction and reductive aldol cyclization of α,β-unsaturated thioesters catalyzed by (BDP)CuH

  摘要：

  已开发出一种由铜氢化物催化、使用PMHS作为化学计量还原剂的α,β-不饱和硫酯的共轭还原反应。1,2-双(二苯膦基)苯（BDP）是该还原反应最有效的配体。当硫醇上的取代基空间要求不高时，可以高产率地生成饱和硫酯。该方案被应用于诱导酮烯硫酯的还原性醛醇环化反应，从而在中等至良好产率下获得β-羟基硫酯。

  DOI：

  10.1039/c1ob05352c
• 作为产物：
  描述：

  2-Methanesulfinyl-3-phenyl-thiopropionic acid S-ethyl ester 120.0 ℃ 、20.0 kPa 条件下， 反应 1.0h， 以90.9%的产率得到Zimtsaeure-thioethylester
  参考文献：
  名称：

  Wladislaw, B.; Marzorati, L.; Gruber, J., Synthetic Communications, 1990, vol. 20, # 18, p. 2937 - 2944

  摘要：

  DOI：

文献信息

• Synthesis of Thioesters by Simultaneous Activation of Carboxylic Acids and Alcohols Using PPh₃/NBS with Benzyltriethylammonium Tetrathiomolybdate as the Sulfur Transfer Reagent
  作者：Purushothaman Gopinath、Ravindran Sasitha Vidyarini、Srinivasan Chandrasekaran

  DOI：10.1002/ejoc.200900956

  日期：2009.12

  A new and simple route for the synthesis of thioesters starting from carboxylic acids and alcohols is reported by using tetrathiomolybdate as the key sulfur transfer reagent. Triphenylphosphane and N-bromosuccinimide were used for the activation of the carboxylic acid and alcohol in the same pot followed by the transfer of sulfur from tetrathiomolybdate. Thioesters were obtained in good to moderate

  通过使用四硫代钼酸盐作为关键的硫转移试剂，报道了一种以羧酸和醇为原料合成硫酯的新的简单途径。三苯基膦和 N-溴代琥珀酰亚胺用于在同一锅中活化羧酸和醇，然后从四硫代钼酸盐中转移硫。以良好至中等的产率获得硫酯。伯醇显示出极好的反应性并给出相应硫酯的良好产率，而仲醇给出适中的产率，而叔醇的反应性非常低并且相应硫酯的产率很低。
• A Novel Transesterification of Thioesters with Alcohols by an Electrochemical Activation
  作者：Masahiko Yamaguchi、Yukiharu Tsukamoto、Toru Minami

  DOI：10.1246/cl.1990.1223

  日期：1990.7

  Esters were synthesized from thioesters and alcohols in high yields by an electrochemical activation. Different results were obtained by the use of n-Bu4N+ I− and LiBF4 as the electrolyte.

  通过电化学活化法，从硫代酯和醇中高产率地合成了酯。使用 n-Bu4N+ I- 和 LiBF4 作为电解质得到了不同的结果。
• Biomimetic Photocycloaddition of 3-Hydroxyflavones: Synthesis and Evaluation of Rocaglate Derivatives as Inhibitors of Eukaryotic Translation
  作者：Stéphane P. Roche、Regina Cencic、Jerry Pelletier、John A. Porco

  DOI：10.1002/anie.201003212

  日期：2010.9.3

  Shedding light on translation: A light‐driven, biomimetic [3+2] cycloaddition has been achieved with the synthesis of a series of rocaglate derivatives. Mechanistic data suggest the possibility for donor–acceptor interactions and the involvement of triplet biradicaloids in the photoexcited state. Several new rocaglate derivatives approach the potency of the anticancer agent silvestrol.

  阐明翻译：通过合成一系列 rocaglate 衍生物，实现了光驱动的仿生 [3+2] 环加成。机械数据表明供体 - 受体相互作用的可能性以及三线态双自由基参与光激发状态的可能性。几种新的 rocaglate 衍生物接近抗癌剂 silvestrol 的效力。
• THE REACTION OF TRIMETHYLSILYL SULFIDES WITH CARBOXYLIC ESTERS. A CONVENIENT METHOD FOR THE PREPARATION OF THIOLESTERS
  作者：Teruaki Mukaiyama、Takeshi Takeda、Kunio Atsumi

  DOI：10.1246/cl.1974.187

  日期：1974.2.5

  In the presence of AlCl3, trimethylsilyl sulfides react with carboxylic esters to give the corresponding thiolesters in high yields.

  在 AlCl3 存在下，三甲基甲硅烷基硫化物与羧酸酯反应以高产率得到相应的硫醇酯。
• Catalytic Enantioselective Synthesis of Vicinal Dialkyl Arrays
  作者：Anthoni W. van Zijl、Wiktor Szymanski、Ferrnando López、Adriaan J. Minnaard、Ben L. Feringa

  DOI：10.1021/jo8010649

  日期：2008.9.19

  With a consecutive "asymmetric allylic alkylation (AAA)/cross-metathesis (CM)/conjugate addition (CA)" protocol it is possible to synthesize either stereoisomer of compounds containing a vicinal dialkyl array with excellent stereoselectivity. The versatility of this protocol in natural product synthesis is demonstrated in the preparation of the ant pheromones faranal and lasiol.