Methanesulfonic acid (4Z,8Z)-12-(tetrahydro-pyran-2-yloxy)-dodeca-4,8-diene-2,6,10-triynyl ester | 1027234-96-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: Methanesulfonic acid (4Z,8Z)-12-(tetrahydro-pyran-2-yloxy)-dodeca-4,8-diene-2,6,10-triynyl ester
• 英文别名: [(4Z,8Z)-12-(oxan-2-yloxy)dodeca-4,8-dien-2,6,10-triynyl] methanesulfonate
• CAS: 1027234-96-3
• 化学式: C₁₈H₂₀O₅S
• 分子量: 348.42
• InChiKey: HAYGKGMEEZMNQS-PEPZGXQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (4Z,8Z)-12-(tetrahydro-pyran-2-yloxy)-dodeca-4,8-diene-2,6,10-triynyl ester 在 sodium hydroxide 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (Z,Z)-12-[(2-tetrahydropyranyl)oxy]-1-(phenylsulfonyl)dodeca-4,8-diene-2,6,10-triyne
  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：

  哌喃 在 bis-triphenylphosphine-palladium(II) chloride 、 四(三苯基膦)钯 copper(l) iodide 、 四丁基氟化铵 、 正丁胺 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 Methanesulfonic acid (4Z,8Z)-12-(tetrahydro-pyran-2-yloxy)-dodeca-4,8-diene-2,6,10-triynyl ester
  参考文献：
  名称：

  Synthesis, Double Cycloaromatization, and DNA-Cleaving Activities of (Z,Z)-11-Sulfonylundeca-3,7-diene-1,5,9-triyne System

  摘要：

  DOI：

  10.1021/jo970513x

文献信息

• Allene-Eneyne Related Cycloaromatization: Design and Synthesis of New DNA-Cleaving Compounds
  作者：Ming-Jung Wu、Chi-Fong Lin、Pao-Tzu Jing、Li-Juan Chang、Tsai-Hui Duh、Fang-Chen Lee、Huey-Ting Chen

  DOI：10.1002/jccs.199800072

  日期：1998.8

  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.
• Synthesis, Double Cycloaromatization, and DNA-Cleaving Activities of (<i>Z</i>,<i>Z</i>)-11-Sulfonylundeca-3,7-diene-1,5,9-triyne System
  作者：Chi-Fong Lin、Ming-Jung Wu

  DOI：10.1021/jo970513x

  日期：1997.6.1