(Z)-2-bromo-1-naphthalen-1-ylundec-1-en-4,10-diyn-3-ol | 329315-85-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-2-bromo-1-naphthalen-1-ylundec-1-en-4,10-diyn-3-ol
• CAS: 329315-85-7
• 化学式: C₂₁H₁₉BrO
• 分子量: 367.285
• InChiKey: OYHJPSXATKDCER-SILNSSARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• 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：

  (Z)-2-bromo-1-naphthalen-1-ylundec-1-en-4,10-diyn-3-ol 在 4-二甲氨基吡啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 二乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 13.5h， 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
• 作为产物：
  描述：

  1,7-辛二炔 、 (Z)-2-bromo-3-(naphthalen-1-yl)acrylaldehyde 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以80%的产率得到(Z)-2-bromo-1-naphthalen-1-ylundec-1-en-4,10-diyn-3-ol
  参考文献：
  名称：

  First synthesis of a highly strained cyclodeca-1,5-diyne skeleton via intramolecular Sonogashira cross-coupling

  摘要：

  Cyclization of alkenyl bromides 6 and 11 containing a terminal alkyne was achieved by using an intramolecular cross-coupling reaction catalyzed by Pd(0) and Cu(I). Under the optimal reaction conditions, cyclodeca-1,5-diyne derivatives 7 and 12 were obtained in 43 and 28% yields, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01890-6

文献信息

• 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.
• First synthesis of a highly strained cyclodeca-1,5-diyne skeleton via intramolecular Sonogashira cross-coupling
  作者：Wei-Min Dai、Anxin Wu

  DOI：10.1016/s0040-4039(00)01890-6

  日期：2001.1

  Cyclization of alkenyl bromides 6 and 11 containing a terminal alkyne was achieved by using an intramolecular cross-coupling reaction catalyzed by Pd(0) and Cu(I). Under the optimal reaction conditions, cyclodeca-1,5-diyne derivatives 7 and 12 were obtained in 43 and 28% yields, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.