(4Z)-1,9-dibromo-6-<(tetrahydro-2-pyranyl)oxy>-4-nonene-2,7-diyne | 144950-50-5

• 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: (4Z)-1,9-dibromo-6-<(tetrahydro-2-pyranyl)oxy>-4-nonene-2,7-diyne
• CAS: 144950-50-5
• 化学式: C₁₄H₁₆Br₂O₂
• 分子量: 376.088
• InChiKey: DAAWACBGNCCOTC-UQCOIBPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4Z)-1,9-dibromo-6-<(tetrahydro-2-pyranyl)oxy>-4-nonene-2,7-diyne 在 甲醇 、 sodium sulfide 、 camphor-10-sulfonic acid 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (5Z)-7-<(7-methoxy-2-(methoxymethyl)-5-methyl-1-naphthoyl)oxy>-1-thia-5-cyclodecene-3,8-diyne
  参考文献：
  名称：

  Molecular Design, Chemical Synthesis, and Study of Novel Enediyne-Sulfide Systems Related to the Neocarzinostatin Chromophore

  摘要：

  The design and synthesis of the novel monocyclic enediyne-sulfide systems and their chemical and DNA cleavage properties are described. The parent enediyne-sulfide 6 possessing a hydroxy group at the allylic position was effectively synthesized via the cross-coupling of the cis-vinyl iodide 11 and the acetylene derivative 12 using a Pd(O)-Cu(I) catalyst and the cyclization reaction of the acyclic dibromide 20 employing sodium sulfide as the key steps. In addition, the esterifications of 6 using appropriate procedures provided a series of its simple derivatives 21-29 and the hybrids 38-44 containing naturally occurring intercalators, all of which are quite stable when handled at ambient temperature. The representative enediyne-sulfide 22 was smoothly aromatized by 1,8-diazabicyclo[5.4.0]undec-7-ene in cyclohexa-1,4-diene through radical pathways and by a hydroxy anion in dimethyl sulfoxide-Tris-HCl, pH 8.5 buffer through a polar pathway. Furthermore, it was clearly found that all enediyne-sulfides cleaved DNA under alkaline conditions without any additive and the hybrids 38 and 44, each of which has the aromatic moiety of the neocarzinostatin chromophore and manzamins, respectively, exhibited the strongest DNA cleaving abilities with the identical high purine base (G > A) selectivity.

  DOI：

  10.1021/ja00122a012
• 作为产物：
  描述：

  (4Z)-6-<(tetrahydro-2-pyranyl)oxy>-4-nonene-2,7-diyne-1,9-diol 在 四溴化碳 、 三辛基膦 作用下， 以 乙醚 为溶剂， 反应 1.5h， 以67%的产率得到(4Z)-1,9-dibromo-6-<(tetrahydro-2-pyranyl)oxy>-4-nonene-2,7-diyne
  参考文献：
  名称：

  设计和合成具有与新carcarinostatin发色团有关的DNA裂解特性的1-thia-3,8-diyn-5-ene系统

  摘要：

  1-硫杂-3,8-二炔-5-烯化合物5 - 10，其是化合物母体的衍生物1在具有高稳定性的短步骤合成; 这些化合物在没有任何添加剂的情况下在碱性条件下显示出DNA裂解活性。

  DOI：

  10.1039/c39920001306