S-phenyl 3-(phenylthio)propanethioate | 87797-69-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: S-phenyl 3-(phenylthio)propanethioate
• 英文别名: S-phenyl 3-(phenylthio)thiopropionate；3-phenylsulfanyl-thiopropionic acid S-phenyl ester；3-Phenylmercapto-thiopropionsaeure-S-phenylester；Thiophenol, S-[3-phenylthiopropionyl]-；S-phenyl 3-phenylsulfanylpropanethioate
• CAS: 87797-69-1
• 化学式: C₁₅H₁₄OS₂
• 分子量: 274.408
• InChiKey: LVHKEWCDKLXDHC-UHFFFAOYSA-N

物化性质

• 沸点：
  233-235 °C(Press: 7 Torr)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-phenyl 3-(phenylthio)propanethioate 在 N-氯代丁二酰亚胺 、 三乙胺 、 3-氯苯甲酸 作用下， 以 四氯化碳 、 乙醚 、 氯仿 为溶剂， 反应 7.0h， 生成 S-phenyl (E)-3-(phenylsulfonyl)propenethioate
  参考文献：
  名称：

  Haynes, Richard K.; Vonwiller, Simone C.; Stokes, John P., Australian Journal of Chemistry, 1988, vol. 41, # 6, p. 881 - 895

  摘要：

  DOI：
• 作为产物：
  描述：

  3-苯硫基丙酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 S-phenyl 3-(phenylthio)propanethioate
  参考文献：
  名称：

  A General Diastereoselective Synthesis of Spiroacetals Related to Those in Ionophores via the Reaction of Lactones with Cerium(III) .gamma.-Cerioalkoxide. MAD Reverses the Diastereoselectivity of the Addition of Methylmetallics to a .beta.-Keto Ether

  摘要：

  The following steps constitute a fairly general and stereoselective synthesis of spiroacetals. 1. Thiophenol is added to acrylic acid. 2. The latter is treated consecutively with butyllithium, CeCl3, and an organolithium compound. 3. The resulting 3-(phenylthio) ketone is either reduced in the presence of zinc ion to yield mainly one diastereomer or treated with methyllithium or methylmagnesium chloride in the presence or absence of methylaluminum bis(2,6-di-tert-butyl-4-mthylphenoxide) (MAD, 25) to yield selectively either of two diastereomeric 3-(phenylthio) alcohols. 4. The alcohol is treated with butyllithium, lithium 4,4'-di-tert-butylbiphenylide (LDBB), and CeCl3, to yield a cerium(III) gamma-cerioalkoxide, which is added to a lactone, the reaction being quenched with acid. In the addition to the keto ether in the absence of MAD, methyllithium or methylmagnesium chloride give very predominantly the erythro alcohol, presumably via Cram's chelate model, while in the presence of excess MAD, the three product is very predominant, possibly because each oxygen atom is complexed with the bulky aluminum reagent. The methodology is demonstrated by the preparation of diastereomeric spiroacetals related to those found in a number of natural ionophores by using as the reaction partner of the carboxylate salt, alpha-lithio tetrahydrofuran or tetrahydropyran, readily generated by reductive lithiation of the corresponding alpha-(phenylthio) heterocycle with LDBB, and by employing methylmetallics rather than reducing agents for the reaction with the ketone.

  DOI：

  10.1021/jo00090a036

文献信息

• Palladium-Catalyzed Carbonylation of Disulfides and Ethylene: Synthesis of β-Thiopropionate Thioesters
  作者：Jian-Xing Xu、Zhi-Peng Bao、Xiao-Feng Wu

  DOI：10.1021/acs.orglett.2c00422

  日期：2022.3.11

  monoxide (C1) and ethylene (C2) into high value-added chemicals is of great significance from an economic perspective, especially to multifunctionalized C3 compounds. Herein, we developed a palladium-catalyzed thiocarbonylative 1,2-difunctionalization of ethylene. Employing NiXantPhos as the ligand and DCE as the solvent, a series of organic disulfides can be successfully transformed into β-thiopropionate

  从经济角度看，将一氧化碳（C1）和乙烯（C2）转化为高附加值化学品具有重要意义，尤其是对多功能化C3化合物而言。在此，我们开发了一种钯催化的乙烯硫羰基化 1,2-双官能化。以NiXantPhos为配体，DCE为溶剂，一系列有机二硫化物可成功转化为高收率的β-硫代丙酸硫酯。
• Ph₃P-mediated decarboxylative ring-opening of maleic anhydride by thiolic compounds: formation of two carbon–sulfur bonds
  作者：N. Nowrouzi、M. Abbasi、Z. Zellifard

  DOI：10.1039/d3ra00294b

  日期：——

  In this study, a simple and efficient method for the formation of carbon–sulfur bonds is described. In this process, ring opening of maleic anhydride by thiols or disulfides and triphenylphosphine led to the formation of sulfide products via formation of two carbon-sulfur bonds.

  在这项研究中，描述了一种形成碳硫键的简单有效的方法。在此过程中，马来酸酐被硫醇或二硫化物和三苯基膦开环，通过形成两个碳硫键形成硫化物产物。
• 一种制备β-硫代丙酸硫酯的方法
  申请人：中国科学院大连化学物理研究所

  公开号：CN116655506A

  公开（公告）日：2023-08-29

  本发明涉及一种制备β‑硫代丙酸硫酯的方法。具体地说在钯和膦配体的催化条件下，二苯基二硫醚与乙烯经羰基化制备β‑硫代丙酸硫酯。本发明以工业中最基础的乙烯和一氧化碳为原料，在催化量的钯催化剂作用下，高原子利用率、高收率地获得了C3双官能化产物β‑硫代丙酸硫酯。
• Preparation of Thiolmethacrylate Esters. A Study of the Reaction of Sodium Mercaptides with Methacrylyl Chloride¹
  作者：Gene Sumrell、George E. Ham、Edwin D. Hornbaker

  DOI：10.1021/ja01543a036

  日期：1958.5
• Jigajinni, Veerappa B.; Wightman, Richard H., Journal of Chemical Research, Miniprint, 1983, # 8, p. 1801 - 1812
  作者：Jigajinni, Veerappa B.、Wightman, Richard H.

  DOI：——

  日期：——