2-(4-(Propyn-3-yloxy)butyl)-1,3-dithiane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: 2-(4-(Propyn-3-yloxy)butyl)-1,3-dithiane
• 英文别名: 2-(4-Prop-2-ynoxybutyl)-1,3-dithiane
• 化学式: C₁₁H₁₈OS₂
• 分子量: 230.395
• InChiKey: AZYIHVRNWXAEMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(4-Chlorobutyl)-1,3-dithiane 在 sodium hydride 、 2-丙炔-1-醇 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以52%的产率得到2-(4-(Propyn-3-yloxy)butyl)-1,3-dithiane
  参考文献：
  名称：

  Tumor-Targeted Boranes. 4. Synthesis of Nitroimidazole-Carboranes with Polyether-Isoxazole Links

  摘要：

  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.

  DOI：

  10.1021/jo00102a026

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.