(5Z)-1-thia-5-cyclodecene-3,8-diyn-7-ol | 144950-38-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5Z)-1-thia-5-cyclodecene-3,8-diyn-7-ol
• 英文别名: (6Z)-1-thiacyclodec-6-en-3,8-diyn-5-ol
• CAS: 144950-38-9
• 化学式: C₉H₈OS
• 分子量: 164.228
• InChiKey: GKHKXMZLELCPJA-DJWKRKHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (5Z)-1-thia-5-cyclodecene-3,8-diyn-7-ol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以88%的产率得到C₉H₈O₃S
  参考文献：
  名称：

  Cycloaromatization and DNA cleavage of novel enyne-allene systems

  摘要：

  通过间氯过苯甲酸氧化相应的烯二炔硫化物 1-4 制备了新型烯二炔砜 5-8；烯二炔砜 6-8 在烯丙基位置上具有离去基团，经 1,8- 二氮杂双环[5.4.0]十一-7-烯（DBU）-viathe 烯二炔-库莫烯中间体 10 芳香化后，在基本条件下显示出 DNA 切断活性，无需任何添加剂。

  DOI：

  10.1039/c39930001406
• 作为产物：
  描述：

  (4Z)-1,9-bis<(tert-butyldiphenylsilyl)oxy>-6-<(tetrahydro-2-pyranyl)oxy>-4-nonene-2,7-diyne 在 sodium sulfide 、 四溴化碳 、 三辛基膦 、 camphor-10-sulfonic acid 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 为溶剂， 反应 8.0h， 生成 (5Z)-1-thia-5-cyclodecene-3,8-diyn-7-ol
  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

文献信息

• Design, synthesis and DNA cleaving profiles of hybrids containing the novel enediyne and naturally occurring DNA intercalates
  作者：Kazunobu Toshima、Kazumi Ohta、Aya Ohashi、Takatsugu Nakamura、Masaya Nakata、Shuichi Matsumura

  DOI：10.1039/c39930001525

  日期：——

  The designed hybrids 5–11 containing the DNA cleavable enediyne 4 and naturally occurring DNA intercalators 12–18cleave DNA effectively under alkaline conditions without any additive; the hybrids 5 and 11 exhibit the strongest DNA-cleaving abilities with the identical high purine base (G>A) selectivities for their DNA-cleavage profiles.

  所设计的杂种5 - 11含有该DNA可切割的烯二炔4和天然存在的DNA嵌入剂12 - 18有效下没有任何添加剂的碱性条件下切割DNA; 杂种5和11表现出最强的DNA切割能力，并具有相同的高嘌呤碱基（G> A）选择性，可用于其DNA切割过程。
• Molecular Design, Chemical Synthesis, and Study of Novel Enediyne-Sulfide Systems Related to the Neocarzinostatin Chromophore
  作者：Kazunobu Toshima、Kazumi Ohta、Aya Ohashi、Takatsugu Nakamura、Masaya Nakata、Kuniaki Tatsuta、Shuichi Matsumura

  DOI：10.1021/ja00122a012

  日期：1995.5

  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.
• Design and synthesis of 1-thia-3,8-diyn-5-ene systems with DNA-cleaving properties related to the neocarzinostatin chromophore
  作者：Kazunobu Toshima、Kazumi Ohta、Aya Ohashi、Atsuo Ohtsuka、Masaya Nakata、Kuniaki Tatsuta

  DOI：10.1039/c39920001306

  日期：——

  1-Thia-3,8-diyn-5-ene compounds 5–10, which are derivatives of the parent compound 1 are synthesized in a short step with high stability; these compounds show DNA-cleaving activity under basic conditions in the absence of any additives.

  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。
• Cycloaromatization and DNA cleavage of novel enyne-allene systems
  作者：Kazunobu Toshima、Kazumi Ohta、Atsuo Ohtsuka、Shuichi Matsumura、Masaya Nakata

  DOI：10.1039/c39930001406

  日期：——

  The novel enyne-allene sulfones 5–8 were prepared by m-chloroperbenzoic acid oxidation of the corresponding enediyne sulfides 1–4; the enyne-allene sulfones 6–8 having a leaving group at the allylic position were aromatized by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)viathe allene-ene-cumulene intermediate 10 and showed DNA-cleaving activities under basic conditions without any additive.

  通过间氯过苯甲酸氧化相应的烯二炔硫化物 1-4 制备了新型烯二炔砜 5-8；烯二炔砜 6-8 在烯丙基位置上具有离去基团，经 1,8- 二氮杂双环[5.4.0]十一-7-烯（DBU）-viathe 烯二炔-库莫烯中间体 10 芳香化后，在基本条件下显示出 DNA 切断活性，无需任何添加剂。