methyl 2-(tert-butyldisulfanyl)benzoate | 927270-06-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-(tert-butyldisulfanyl)benzoate
• 英文别名: tert-butyl o-methoxycarbonylphenyl disulfide；Methyl 2-(tert-butyldisulfanyl)benzoate
• CAS: 927270-06-2
• 化学式: C₁₂H₁₆O₂S₂
• 分子量: 256.39
• InChiKey: ICVYHPGYENEYHF-UHFFFAOYSA-N

物化性质

• 沸点：
  332.6±34.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  76.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  硫代水杨酸甲酯 在 T406石油添加剂 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 2-(tert-butyldisulfanyl)benzoate
  参考文献：
  名称：

  New Excursions Into the Synthesis and Medicinal Chemistry of the Disulfide Bond

  摘要：

  The presentation discusses two themes of current interest in my research group in conjunction with a garlic mimics program. The first involves a new one-pot methodology for preparing unsymmetrical disulfides in high yield using 1-chlorobenzotriazole (BtCl) as oxidant, which can be applied to a range of functional types. The second part of the lecture will discuss the synthesis of derivatives of the garlic-derived natural product ajoene, in conjunction with an anti-cancer screening program. The synthesis has been used to prepare a fluorescently tagged derivative of the natural product that has been used to investigate localization and mode of action within the cancer cell using confocal laser scanning microscopy.

  DOI：

  10.1080/10426507.2012.736107

文献信息

• One-pot synthesis of unsymmetrical disulfides using 1-chlorobenzotriazole as oxidant: Interception of the sulfenyl chloride intermediate
  作者：Nashia Stellenboom、Roger Hunter、Mino R. Caira

  DOI：10.1016/j.tet.2010.02.077

  日期：2010.4

  is described for unsymmetrical disulfide synthesis from two different thiols using 1-chlorobenzotriazole (BtCl) as oxidant. The mechanism of the coupling involves in situ trapping of the sulfenyl chloride intermediate R1SCl by nucleophilic benzotriazole (BtH) to form R1SBt, which protects R1SCl from forming the homodimer R1SSR1. The methodology is applicable to all types of thiol (aliphatic, aromatic

  描述了一种高产，低温的一锅法，用于使用1-氯苯并三唑（BtCl）作为氧化剂由两种不同的硫醇合成不对称的二硫键。偶联的机制包括通过亲核苯并三唑（BtH）原位捕获亚磺酰氯中间体R 1 SCl形成R 1 SBt，从而保护R 1 SCl避免形成同型二聚体R 1 SSR 1。该方法适用于所有类型的硫醇（脂族，芳族，杂芳族），并为脂族-脂族偶联开发了一种变体。差异性的N-保护的半胱氨酸偶合，以高收率（90％）提供不对称的胱氨酸衍生物，该模型可作为含半胱氨酸的肽单分子间偶联形成肽二硫键异二聚体的模型。由于条件温和，因此注意到芳香族-芳香族二硫化物合成中的交换最少。
• Sandmeyer-Type Reductive Disulfuration of Anilines
  作者：Shiqi Chen、Si Cao、Chaoyang Liu、Baoxu Wang、Xiaorui Ren、Hang Huang、Zhihong Peng、Xi Wang

  DOI：10.1021/acs.orglett.1c02636

  日期：2021.10.1

  can be considered as a reductive disulfuration variation of the classic Sandmeyer reaction, is performed under mild conditions and exhibits broad scope across the aniline substrate and disulfur transfer reagent classes. The gram-scale synthesis of disulfides is successfully achieved through this method, rendering the approach highly valuable.

  本文报道了苯胺与二硫转移试剂（二硫代磺酸盐或四硫化物）的无过渡金属/配体二硫化。该反应可以被认为是经典 Sandmeyer 反应的还原二硫变化，在温和的条件下进行，并在苯胺底物和二硫转移试剂类别中表现出广泛的范围。通过这种方法成功地实现了二硫化物的克级合成，使该方法具有很高的价值。
• New Excursions Into the Synthesis and Medicinal Chemistry of the Disulfide Bond
  作者：Roger Hunter*、Catherine Kaschula、Nashia Stellenboom、Jonathan Cotton、M. Iqbal Parker

  DOI：10.1080/10426507.2012.736107

  日期：2013.11.1

  The presentation discusses two themes of current interest in my research group in conjunction with a garlic mimics program. The first involves a new one-pot methodology for preparing unsymmetrical disulfides in high yield using 1-chlorobenzotriazole (BtCl) as oxidant, which can be applied to a range of functional types. The second part of the lecture will discuss the synthesis of derivatives of the garlic-derived natural product ajoene, in conjunction with an anti-cancer screening program. The synthesis has been used to prepare a fluorescently tagged derivative of the natural product that has been used to investigate localization and mode of action within the cancer cell using confocal laser scanning microscopy.