10-[1-Naphthalen-2-yl-meth-(E)-ylidene]-cyclodeca-2,8-diynol | 359400-21-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 10-[1-Naphthalen-2-yl-meth-(E)-ylidene]-cyclodeca-2,8-diynol
• 英文别名: (10E)-10-(naphthalen-2-ylmethylidene)cyclodeca-2,8-diyn-1-ol
• CAS: 359400-21-8
• 化学式: C₂₁H₁₈O
• 分子量: 286.373
• InChiKey: WEAMARWRTAQOEU-CAPFRKAQSA-N

物化性质

• 沸点：
  514.0±50.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  甲氧基乙酸 、 10-[1-Naphthalen-2-yl-meth-(E)-ylidene]-cyclodeca-2,8-diynol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以65%的产率得到(E)-3-methoxyacetoxy-4-(2'-naphthylmethylidene)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
• 作为产物：
  描述：

  1,7-辛二炔 在 copper(l) iodide 、 四(三苯基膦)钯 吗啉 、 N-乙基哌啶 、 chromium dichloride 、 碘 、 二异丁基氢化铝 、 pyridinium chlorochromate 、 nickel dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 9.0h， 生成 10-[1-Naphthalen-2-yl-meth-(E)-ylidene]-cyclodeca-2,8-diynol
  参考文献：
  名称：

  Intramolecular Nozaki–Hiyama–Kishi reactions and Ln(III)-catalyzed allylic rearrangement as the key steps towards 10-membered ring enediynes

  摘要：

  A general and facile synthesis of the 3-substituted 10-membered ring enediynes 18-22 from the aldehydes 8 and 15 has been established by utilizing the intramolecular Nozaki-Hiyama-Kishi reaction and the lwanthanide(III)-catalyzed rearrangement of allylic alkoxyacetates as the key steps. This work provides ready access to the (E)-3-acyloxy-4-(arylmethylidene)cyclodeca-1,5-diynes, which can be converted into the bioactive enediynes under physiological conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00707-9

文献信息

• US6391916B1
  申请人：——

  公开号：US6391916B1

  公开（公告）日：2002-05-21
• Intramolecular Nozaki–Hiyama–Kishi reactions and Ln(III)-catalyzed allylic rearrangement as the key steps towards 10-membered ring enediynes
  作者：Wei-Min Dai、Anxin Wu、Wataru Hamaguchi

  DOI：10.1016/s0040-4039(01)00707-9

  日期：2001.6

  A general and facile synthesis of the 3-substituted 10-membered ring enediynes 18-22 from the aldehydes 8 and 15 has been established by utilizing the intramolecular Nozaki-Hiyama-Kishi reaction and the lwanthanide(III)-catalyzed rearrangement of allylic alkoxyacetates as the key steps. This work provides ready access to the (E)-3-acyloxy-4-(arylmethylidene)cyclodeca-1,5-diynes, which can be converted into the bioactive enediynes under physiological conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.