5-(2-(methylthio)propyl)benzo[d][1,3]dioxole | 5304-81-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-(2-(methylthio)propyl)benzo[d][1,3]dioxole
• CAS: 5304-81-4
• 化学式: C₁₁H₁₄O₂S
• 分子量: 210.297
• InChiKey: IONSXDWJRQKNDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-(2-(methylthio)propyl)benzo[d][1,3]dioxole 在 三氯化硼 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 4-(2-Methylsulfanyl-propyl)-benzene-1,2-diol
  参考文献：
  名称：

  Dopaminergic agonists: comparative actions of amine and sulfonium analogs of dopamine

  摘要：

  We have investigated the possibility that structural modifications of the sulfonium analogue of dopamine (4) would produce the same pattern of biological activity as structural modifications of dopamine. A series of methyl- tetralinyl -, and naphthalenylsulfonium analogues 5-7 were prepared and tested for their ability to inhibit the potassium-evoked release of [3H]acetylcholine from striatal slices. All compounds were tested under normal conditions and after depletion of dopamine stores with reserpine and alpha-methyl-p-tyrosine. The amine and sulfonium analogues 2-6 all showed direct agonist activity. The sulfonium analogue 7 produced, predominantly, indirect activity. In contrast to the amine analogues, chemical modifications of the sulfonium compounds produced little change in their dopamine agonist activity.

  DOI：

  10.1021/jm00371a021
• 作为产物：
  描述：

  2-(methylsulfinyl)-3',4'-(methylenedioxy)propiophenone 在 三乙基硅烷 、 三甲基氯硅烷 、 三氟乙酸 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 9.0h， 生成 5-(2-(methylthio)propyl)benzo[d][1,3]dioxole
  参考文献：
  名称：

  Dopaminergic agonists: comparative actions of amine and sulfonium analogs of dopamine

  摘要：

  We have investigated the possibility that structural modifications of the sulfonium analogue of dopamine (4) would produce the same pattern of biological activity as structural modifications of dopamine. A series of methyl- tetralinyl -, and naphthalenylsulfonium analogues 5-7 were prepared and tested for their ability to inhibit the potassium-evoked release of [3H]acetylcholine from striatal slices. All compounds were tested under normal conditions and after depletion of dopamine stores with reserpine and alpha-methyl-p-tyrosine. The amine and sulfonium analogues 2-6 all showed direct agonist activity. The sulfonium analogue 7 produced, predominantly, indirect activity. In contrast to the amine analogues, chemical modifications of the sulfonium compounds produced little change in their dopamine agonist activity.

  DOI：

  10.1021/jm00371a021

文献信息

• Catalyst-free photochemical reactions of alkyl dihydropyridines <i>via</i> modulation of chromophores and light wavelength
  作者：Yanzhu Liu、Zhonglin Zhang、Zhixin Wei、Zhiying Zhong、Shiwen Liu、Yi Yang、Xiaojun Zeng

  DOI：10.1039/d2nj05901k

  日期：——

  describes an environmentally friendly strategy for thiolation and trifluoromethylthiolation of Hantzsch esters. The alkyl radical could be generated smoothly without any photocatalyst via modification of chromophores of alkyl dihydropyridines and wavelength of light. Besides, a broad alkyl dihydropyridine substrate scope and high functional group tolerance are observed. In addition, the modulation of

  本研究描述了 Hantzsch 酯的硫醇化和三氟甲基硫醇化的环保策略。通过改变烷基二氢吡啶的发色团和光的波长，可以在没有任何光催化剂的情况下顺利地产生烷基自由基。此外，观察到广泛的烷基二氢吡啶底物范围和高官能团耐受性。此外，发色团和波长的调制适用于其他功能化，例如烷基二氢吡啶的卤化和炔基化。
• Visible-Light-Promoted Cross-Coupling Reactions of 4-Alkyl-1,4-dihydropyridines with Thiosulfonate or Selenium Sulfonate: A Unified Approach to Sulfides, Selenides, and Sulfoxides
  作者：Jian Li、Xin-Er Yang、Shan-Le Wang、Long-Long Zhang、Xiao-Zhou Zhou、Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1021/acs.orglett.0c01776

  日期：2020.6.19

  In this paper, a visible-light-promoted cross-coupling of 4-alkyl-1,4-dihydropyridines with thio-/selenium sulfonates under transition-metal-free conditions is described. This strategy features easily available substrates, mild reaction conditions, high yields, and high chemoselectivity. A novel synthetic route for the construction of a sulfide or selenide C-sp3-S or C-sp3-Se bond under transition-metal-free conditions without an additive oxidant or base is developed. This method is well extended to the synthesis of a class of thiolated or selenylated glycosides that has not been explored before. Sulfoxides were also successfully chemoselectively observed via a facile variation of the atmosphere under photocatalyzed conditions.