(E)-3-Acetoxy-4-[(4'-methoxyphenyl)methylidene]cyclodeca-1,5-diyne | 404869-46-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-3-Acetoxy-4-[(4'-methoxyphenyl)methylidene]cyclodeca-1,5-diyne
• 英文别名: [(10E)-10-[(4-methoxyphenyl)methylidene]cyclodeca-2,8-diyn-1-yl] acetate
• CAS: 404869-46-1
• 化学式: C₂₀H₂₀O₃
• 分子量: 308.377
• InChiKey: YUDRGCQUHWENGL-OBGWFSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-Acetoxy-4-[(4'-methoxyphenyl)methylidene]cyclodeca-1,5-diyne 以72%的产率得到(E)-3-Acetoxy-4-[(4'-((trimethylacetyl)oxy)phenyl)methylidene]cyclodeca-1,5-diyne
  参考文献：
  名称：

  Enediyne derivatives

  摘要：

  可以通过新颖的合成方法，使用起始物(E)-C3-取代-4-(芳基或杂环芳基甲基)环十碳-1,5-二炔试剂，制备新颖的C3-取代环十碳-1,5-二炔。与未取代的对应物相比，这些C3-取代环十碳-1,5-二炔-3-烯和起始试剂都具有更好的热稳定性。

  公开号：

  US06391916B1
• 作为产物：
  描述：

  (E)-10-Iodo-2-[(4'-methoxyphenyl)methylidene]deca-3,9-diynal 在 chromium dichloride 、 4-二甲氨基吡啶 、 nickel dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 (E)-3-Acetoxy-4-[(4'-methoxyphenyl)methylidene]cyclodeca-1,5-diyne
  参考文献：
  名称：

  DNA Cleavage Potency, Cytotoxicity, and Mechanism of Action of a Novel Class of Enediyne Prodrugs

  摘要：

  We have discovered a novel class of (E)-3-acyloxy-4-(arylmethylidene)cyclodeca-1,5-diynes which exhibit promising enediyne-like DNA cleavage and cytotoxic activities. LC-MS analysis of the incubation mixture (pH 8.5, 37 degreesC) confirmed formation of 10-membered ring enediyne presumably via an allylic cation and suggested that the 1,4-benzenoid diradical might be one of the active species for DNA damage and cytotoxicity.

  DOI：

  10.1021/jm015588e

文献信息

• US6391916B1
  申请人：——

  公开号：US6391916B1

  公开（公告）日：2002-05-21
• DNA Cleavage Potency, Cytotoxicity, and Mechanism of Action of a Novel Class of Enediyne Prodrugs
  作者：Wei-Min Dai、Kwong Wah Lai、Anxin Wu、Wataru Hamaguchi、Mavis Yuk Ha Lee、Ling Zhou、Atsushi Ishii、Sei-ichi Nishimoto

  DOI：10.1021/jm015588e

  日期：2002.2.1

  We have discovered a novel class of (E)-3-acyloxy-4-(arylmethylidene)cyclodeca-1,5-diynes which exhibit promising enediyne-like DNA cleavage and cytotoxic activities. LC-MS analysis of the incubation mixture (pH 8.5, 37 degreesC) confirmed formation of 10-membered ring enediyne presumably via an allylic cation and suggested that the 1,4-benzenoid diradical might be one of the active species for DNA damage and cytotoxicity.
• Enediyne derivatives
  申请人：The Hong Kong University of Science and Technology

  公开号：US06391916B1

  公开（公告）日：2002-05-21

  Novel C3-substituted cyclodeca-1,5-diynes can be prepared through novel synthetic procedures using starting (E)-C3-substituted-4-(aryl- or heteroarylmethylidene)cyclodeca-1,5-diynes reagents. Both the C3-substituted cyclodeca-1,5-diyn-3-enes and the starting reagents have improved thermal stability compared to unsubstituted counterparts.

  可以通过新颖的合成方法，使用起始物(E)-C3-取代-4-(芳基或杂环芳基甲基)环十碳-1,5-二炔试剂，制备新颖的C3-取代环十碳-1,5-二炔。与未取代的对应物相比，这些C3-取代环十碳-1,5-二炔-3-烯和起始试剂都具有更好的热稳定性。