Trifluoro-methanesulfonic acid 3-(3-hydroxy-prop-1-ynyl)-naphthalen-2-yl ester | 176384-80-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Trifluoro-methanesulfonic acid 3-(3-hydroxy-prop-1-ynyl)-naphthalen-2-yl ester
• CAS: 176384-80-8
• 化学式: C₁₄H₉F₃O₄S
• 分子量: 330.284
• InChiKey: MGSPHWJASTVADZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid 3-(3-hydroxy-prop-1-ynyl)-naphthalen-2-yl ester 在 palladium on activated charcoal copper(l) iodide 、 四(三苯基膦)钯 、 氢气 、 对甲苯磺酸 、 正丁胺 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 生成 Methanesulfonic acid 3-{3-[3-(tetrahydro-pyran-2-yloxy)-propyl]-naphthalen-2-yl}-prop-2-ynyl ester
  参考文献：
  名称：

  Allene-Eneyne Related Cycloaromatization: Design and Synthesis of New DNA-Cleaving Compounds

  摘要：

  Abstract(Z)‐7‐Sulfonyl‐3‐hexen‐1,5‐diyne containing molecules are stable at room temperature and isomerized to eneyne‐allene‐sulfones under alkaline conditions. These eneyne‐allene‐sulfones were not isolable, spontaneously cyclized to form biradical intermediates under mild conditions, and exhibited good DNA‐cleaving and human tumor cell line growth inhibition properties. Further studies indicated that compounds bearing on aromatic ring at C(3) and C(4), such as 25, proved to be more active against those tumor cell lines. Removal of acetylene unit at C(1) and C(2), made the resulting compound less active. A related compound, (Z,Z)‐12‐(2‐tetrahydropyranyl)oxy‐1‐phenylsulfonyldodeca‐4,8‐diene‐2,6,10‐triyne (37), was synthesized. Upon treatment of triethylamine at refluxing benzene, this compound undergoes double cycloaromatization to form a naphalene adduct, which possesses excellent DNA‐cleaving activity.

  DOI：

  10.1002/jccs.199800072
• 作为产物：
  描述：

  萘-2,3-二基 双(三氟甲磺酸酯) 、 2-丙炔-1-醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁胺 作用下， 以 乙醚 为溶剂， 生成 Trifluoro-methanesulfonic acid 3-(3-hydroxy-prop-1-ynyl)-naphthalen-2-yl ester
  参考文献：
  名称：

  Chemical synthesis, DNA cleavage and antitumor activity of molecules with (Z)-7-sulfonyl-3-hexene-1,5-diyne functionalities

  摘要：

  Compounds 20a-d, 21a, 21d and 22 were synthesized from the corresponding (Z)-1,2-dichloroethylene, 1,2-diiodobenzene and 2,3-naphthylene bistriflate respectively and exhibited DNA cleaving properties at 37 degrees C in pH 8.0 as well as potent cytotoxicity against human carcinoma cells with no additive.

  DOI：

  10.1016/0960-894x(96)00090-x

文献信息

• Synthesis and Biological Activities of Aryl Propargyl Sulfone
  作者：Ming-Jung Wu、Chi-Fong Lin、Li-Juan Chang、Pao-Tzu Jing、Tsai-Hui Duh、Wuan-Ting Tseng、Fang-Chen Lee、Shan-Shue Wang、Hsueh-O Chang

  DOI：10.1002/jccs.199800118

  日期：1998.12

  AbstractA series of molecules containing monopropargyl sulfone or 1, 2‐bis‐propargyl sulfone were synthesized. The cytotoxicity of these compounds against human carcinoma cells was also examined. This study indicated that the formation of a biradical intermediate is important to the potency of cytotoxicity.