3-(prop-2-yn-1-ylthio)propan-1-ol | 1080588-17-5

• 分子结构分类: 有机化合物 - 乙炔化物 - 碳化物
• 英文名称: 3-(prop-2-yn-1-ylthio)propan-1-ol
• 英文别名: 3-Prop-2-ynylsulfanylpropan-1-ol
• CAS: 1080588-17-5
• 化学式: C₆H₁₀OS
• 分子量: 130.211
• InChiKey: KDXFFBSSLASXBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-硝基苯基丝氰酸酯 、 3-(prop-2-yn-1-ylthio)propan-1-ol 在 三丁基膦 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以65%的产率得到(3-((2-nitrophenyl)selanyl)propyl)(prop-2-yn-1-yl)sulfane
  参考文献：
  名称：

  阿霍烯的简短全合成

  摘要：

  我们描述了大蒜主要生物活性成分阿霍烯的简短全合成。大蒜素作为唯一已知的替代起始材料的不稳定性导致开发出一种可靠的方法，用于从简单的结构单元合成阿霍烯，该方法也适用于高档操作。

  DOI：

  10.1002/anie.201808605
• 作为产物：
  描述：

  3-巯基-1-丙醇 、 3-溴丙炔 在 氢氧化钾 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 3-(prop-2-yn-1-ylthio)propan-1-ol
  参考文献：
  名称：

  Substituted ajoenes as novel anti-cancer agents

  摘要：

  A new synthesis of the ajoene pharmacophore core is presented involving the regioselective radical addition of a thiyl radical to a terminal alkyne as the key step. The synthesis allows structural variation of the two end groups on sulfur, and a range of novel derivatives varying the R(1) group (sulfoxide end) has been prepared and tested against CT-1 transformed. broblast cells for anti-cancer activity. The results indicate comparable or even improved activity compared to the parent natural product ajoene isomers. This opens up the way to systematically studying the biology of the ajoene core. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.056

文献信息

• Substituted ajoenes as novel anti-cancer agents
  作者：Roger Hunter、Catherine H. Kaschula、Iqbal M. Parker、Mino R. Caira、Philip Richards、Susan Travis、Francois Taute、Thozama Qwebani

  DOI：10.1016/j.bmcl.2008.08.056

  日期：2008.10

  A new synthesis of the ajoene pharmacophore core is presented involving the regioselective radical addition of a thiyl radical to a terminal alkyne as the key step. The synthesis allows structural variation of the two end groups on sulfur, and a range of novel derivatives varying the R(1) group (sulfoxide end) has been prepared and tested against CT-1 transformed. broblast cells for anti-cancer activity. The results indicate comparable or even improved activity compared to the parent natural product ajoene isomers. This opens up the way to systematically studying the biology of the ajoene core. (c) 2008 Elsevier Ltd. All rights reserved.
• Short Total Synthesis of Ajoene
  作者：Filipa Silva、Shaista S. Khokhar、Danielle M. Williams、Robert Saunders、Gareth J. S. Evans、Michael Graz、Thomas Wirth

  DOI：10.1002/anie.201808605

  日期：2018.9.17

  We describe a short total synthesis of ajoene, a major biologically active constituent of garlic. The instability of allicin as the only other known alternative starting material has led to the development of a reliable procedure for the synthesis of ajoene from simple building blocks that is also suitable for upscale operations.

  我们描述了大蒜主要生物活性成分阿霍烯的简短全合成。大蒜素作为唯一已知的替代起始材料的不稳定性导致开发出一种可靠的方法，用于从简单的结构单元合成阿霍烯，该方法也适用于高档操作。