(E)-3-methoxyacetoxy-4-(1'-naphthylmethylidene)cyclodeca-1,5-diyne | 359400-27-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-3-methoxyacetoxy-4-(1'-naphthylmethylidene)cyclodeca-1,5-diyne
• 英文别名: [(10E)-10-(naphthalen-1-ylmethylidene)cyclodeca-2,8-diyn-1-yl] 2-methoxyacetate
• CAS: 359400-27-4
• 化学式: C₂₄H₂₂O₃
• 分子量: 358.437
• InChiKey: MTPIYIZFIDUFHB-HEHNFIMWSA-N

物化性质

• 沸点：
  557.7±50.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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-methoxyacetoxy-4-(1'-naphthylmethylidene)cyclodeca-1,5-diyne 在 Eu(fod)3 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以59%的产率得到3-[(1'-methoxyacetoxy-1'-(1''-naphthyl))methyl]cyclodeca-3-en-1,5-diyne
  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
• 作为产物：
  描述：

  10-Iodo-2-[1-naphthalen-1-yl-meth-(E)-ylidene]-deca-3,9-diynal 在 chromium dichloride 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 nickel dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 (E)-3-methoxyacetoxy-4-(1'-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

文献信息

• 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.
• 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.