2-nitro-1-<2-<2-(2-prop-2-ynylpxyethoxy)ethoxy>ethyl>imidazole | 154470-32-3

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2-nitro-1-<2-<2-(2-prop-2-ynylpxyethoxy)ethoxy>ethyl>imidazole
• 英文别名: 2-Nitro-1-(2-(2-(2-(propyn-3-yloxy)ethoxy)ethoxy)ethyl)imidazole；2-nitro-1-(2-(2-(1-prop-2-ynyloxyethoxy)ethoxy)ethyl)imidazole；2-Nitro-1-[2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethyl]imidazole
• CAS: 154470-32-3
• 化学式: C₁₂H₁₇N₃O₅
• 分子量: 283.284
• InChiKey: ZSWOCMBQHZQDGQ-UHFFFAOYSA-N

物化性质

• 沸点：
  455.5±55.0 °C(predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  91.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-{4-(hydroxyiminomethyl)phenoxymethyl}-1,2-dicarba-closo-dodecaborane(12) 、 2-nitro-1-<2-<2-(2-prop-2-ynylpxyethoxy)ethoxy>ethyl>imidazole 在 NaOCl 、 H₂O 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到3-{4-(1,2-dicarba-closo-dodecaboran(12)-1-ylmethoxy)phenyl}-5-(2-(2-{2-(2-nitroimidazol-1-yl)ethoxy}ethoxy)methyl)isoxazole
  参考文献：
  名称：

  Tumour-targetted boranes. Part 2. Coupling of closo-carboranes to substituted 2-nitroimidazoles via 1,3-dipolar cycloaddition

  摘要：

  Carboranes targetted to specific tumour tissues are important for boron neutron capture therapy of cancer. Direct syntheses of carboranes linked to 2-nitroimidazole were unsuccessful. A mild procedure for 1,3-dipolar cycloaddition of 4-(carboranylmethoxy)benzonitrile N-oxide 32 with a nitroimidazolyl-alkene 27 and with nitroimidazolyl-alkynes 3 and 30 has been developed. using a series of model reactions, yielding a dihydroisoxazole 28 and the isoxazoles 29 and31. respectively. The nitrile oxide 32 is unusually stable. Dithioacetals are shown to be suitable protecting groups for aromatic aldehydes under the vigorous reductive and Lewis acidic-basic conditions,of carborane formation. 6-Methoxy-4H-[1]benzopyrano[4,3-c]isoxazole 16 been synthesised by intramolecular 1,3-dipolar cycloaddition. The structure of-the isoxazole derivative 29 has been confirmed by an X-ray crystal structure analysis.

  DOI：

  10.1039/p19940000203
• 作为产物：
  描述：

  2-氯乙氧基-2-乙氧基二乙醇 在 potassium tert-butylate 、 sodium hydride 、 potassium iodide 作用下， 反应 14.75h， 生成 2-nitro-1-<2-<2-(2-prop-2-ynylpxyethoxy)ethoxy>ethyl>imidazole
  参考文献：
  名称：

  Tumour-targetted boranes. Part 2. Coupling of closo-carboranes to substituted 2-nitroimidazoles via 1,3-dipolar cycloaddition

  摘要：

  Carboranes targetted to specific tumour tissues are important for boron neutron capture therapy of cancer. Direct syntheses of carboranes linked to 2-nitroimidazole were unsuccessful. A mild procedure for 1,3-dipolar cycloaddition of 4-(carboranylmethoxy)benzonitrile N-oxide 32 with a nitroimidazolyl-alkene 27 and with nitroimidazolyl-alkynes 3 and 30 has been developed. using a series of model reactions, yielding a dihydroisoxazole 28 and the isoxazoles 29 and31. respectively. The nitrile oxide 32 is unusually stable. Dithioacetals are shown to be suitable protecting groups for aromatic aldehydes under the vigorous reductive and Lewis acidic-basic conditions,of carborane formation. 6-Methoxy-4H-[1]benzopyrano[4,3-c]isoxazole 16 been synthesised by intramolecular 1,3-dipolar cycloaddition. The structure of-the isoxazole derivative 29 has been confirmed by an X-ray crystal structure analysis.

  DOI：

  10.1039/p19940000203

文献信息

• Tumor-Targeted Boranes. 4. Synthesis of Nitroimidazole-Carboranes with Polyether-Isoxazole Links
  作者：Martin Scobie、Michael D. Threadgill

  DOI：10.1021/jo00102a026

  日期：1994.11

  Carboranes targeted to specific tumor tissues are important for boron neutron capture therapy (BNCT) of cancer. Previous attempts to use isoxazolylphenyl-linked nitroimidazole-carboranes for targeting to hypoxic tumors were hampered by the low polarity and very low aqueous solubility of the compounds. Syntheses of polyether-linked nitroimidazole-isoxazole-carborane 17, 25, and 26 via 1,3-dipolar cycloaddition of appropriate nitroimidazole-alkynes with nitrile oxides derived from aliphatic aldehyde oximes linked by a varying number of water-solubilizing ether units to carborane have been developed. The stabilities of the nitrile oxides were much less than that of the corresponding 4-(carboranylmethoxy)phenyl nitrile oxide and depended on their structure. The yields of isoxazoles varied accordingly and cycloaddition failed when eight ether units were included in the chain. Compounds 17, 25, and 26, with four, five, and six ether units, respectively, had increasingly convenient physical properties to permit biological evaluation.