1-(Z-6-bromo-3-O-tert-butyldimethylsilyl-2,5,6-trideoxyhept-5-enofuranurononitrile)thymine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(Z-6-bromo-3-O-tert-butyldimethylsilyl-2,5,6-trideoxyhept-5-enofuranurononitrile)thymine
• 英文别名: (Z)-2-bromo-3-[(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]prop-2-enenitrile；(Z)-2-bromo-3-[(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]prop-2-enenitrile
• 化学式: C₁₈H₂₆BrN₃O₄Si
• 分子量: 456.412
• InChiKey: ATROVJKNIPNUII-VJUFAYPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  91.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(Z-6-bromo-3-O-tert-butyldimethylsilyl-2,5,6-trideoxyhept-5-enofuranurononitrile)thymine 在 盐酸 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以80%的产率得到1-(Z-6-bromo-2,5,6-trideoxyhept-5-enofuranurononitrile)thymine
  参考文献：
  名称：

  SYNTHESIS AND IN VITRO CYTOTOXIC AND ANTIVIRAL ACTIVITIES OF 1-(2,5,6-TRIDEOXY-6-HALOGENOHEPT-5-ENOFURANURONONITRILE)THYMINE AND DERIVATIVES

  摘要：

  All 1-(2,5,6-trideoxy-6-halogenohept-5-enofuranurononitrile)thymine and their 3'-O-TBDMS derivatives have been prepared and their configuration established. Some of these compounds are endowed with a cytotoxic or cytostatic activity in cell culture. The single most important factor affecting the cytotoxicity of these compounds is the presence on the molecule of a soft (electrofugal) halogen atom.

  DOI：

  10.1081/ncn-120003285
• 作为产物：
  描述：

  α-Brom-α-cyano-methylen-triphenylphosphoran 、 3'-tert-butyldimethylsilylthymidine 5'-carboxaldehyde 以 苯 为溶剂， 反应 24.0h， 生成 (E)-3-((2R,3S,5R)-3-((tert-butyldimethylsilyl)oxy)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)acrylonitrile 、 1-(E-6-bromo-3-O-tert-butyldimethylsilyl-2,5,6-trideoxyhept-5-enofuranurononitrile)thymine 、 1-(Z-6-bromo-3-O-tert-butyldimethylsilyl-2,5,6-trideoxyhept-5-enofuranurononitrile)thymine
  参考文献：
  名称：

  SYNTHESIS AND IN VITRO CYTOTOXIC AND ANTIVIRAL ACTIVITIES OF 1-(2,5,6-TRIDEOXY-6-HALOGENOHEPT-5-ENOFURANURONONITRILE)THYMINE AND DERIVATIVES

  摘要：

  All 1-(2,5,6-trideoxy-6-halogenohept-5-enofuranurononitrile)thymine and their 3'-O-TBDMS derivatives have been prepared and their configuration established. Some of these compounds are endowed with a cytotoxic or cytostatic activity in cell culture. The single most important factor affecting the cytotoxicity of these compounds is the presence on the molecule of a soft (electrofugal) halogen atom.

  DOI：

  10.1081/ncn-120003285

文献信息

• SYNTHESIS AND IN VITRO CYTOTOXIC AND ANTIVIRAL ACTIVITIES OF 1-(2,5,6-TRIDEOXY-6-HALOGENOHEPT-5-ENOFURANURONONITRILE)THYMINE AND DERIVATIVES
  作者：Jean M.J. Tronchet、Frederic Chalard、Elisabeth Rivara-Minten、Michel Seman、Erik De Clercq、Jan Balzarini、Pierre Dilda

  DOI：10.1081/ncn-120003285

  日期：2002.4.15

  All 1-(2,5,6-trideoxy-6-halogenohept-5-enofuranurononitrile)thymine and their 3'-O-TBDMS derivatives have been prepared and their configuration established. Some of these compounds are endowed with a cytotoxic or cytostatic activity in cell culture. The single most important factor affecting the cytotoxicity of these compounds is the presence on the molecule of a soft (electrofugal) halogen atom.