5-(氯汞)胞苷 | 65523-07-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 5-(氯汞)胞苷
• 英文名称: 5-(Chloromercuri)cytidine
• CAS: 65523-07-1
• 化学式: C₉H₁₂ClHgN₃O₅
• 分子量: 478.254
• InChiKey: DEBWUFGKLVMZFT-WFIJOQBCSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(氯汞)胞苷 、 3-氯丙烯 在 lithium tetrachloropalladate 作用下， 以 甲醇 为溶剂， 以70%的产率得到5-(3-propenyl)cytidine
  参考文献：
  名称：

  C-5-Substituted pyrimidine nucleosides. 3. Reaction of allylic chlorides, alcohols, and acetates with pyrimidine nucleoside derived organopalladium intermediates

  摘要：

  DOI：

  10.1021/jo00320a039

文献信息

• Palladium-mediated synthesis of C-5 pyrimidine nucleoside thioethers from disulfides and mercurinucleosides
  作者：Donald E. Bergstrom、Peter Beal、Jeffrey Jenson、Xiaoping Lin

  DOI：10.1021/jo00019a025

  日期：1991.9

  Thioether-linked side chains can be created at C-5 of pyrimidine nucleosides via a palladium-mediated reaction of mercurated nucleosides with organic disulfides. 5-(Chloromercuri)-2'-deoxyuridine reacts with butyl disulfide, phenyl disulfide, dimethyl 3,3'-dithiodipropionate, and N,N'-bis(trifluoroacetyl)cystamine to yield respectively 5-(1-thiapentyl)-2'-deoxyuridine, 5-(phenylthio)-2'-deoxyuridine, 5-[3-(methoxycarbonyl)-1-thiapropyl]-2'-deoxyuridine, and 5-[3-(trifluoroacetamido)-1-thiapropyl]-2'-deoxyuridine in yields ranging from 46 to 73%. Other mercurated nucleosides, including 5-(chloromercuri)-2'-deoxycytidine, 5-(chloromercuri)cytidine, and 5-(chloromercuri)tubercidin react with N,N'-bis(trifluoroacetyl)cystamine and lithium-palladium chloride in methanol to yield the corresponding coupled products, but the yields are much lower (5-10%). The nucleoside coupling reaction is complicated by competing side reactions between disulfides and Pd2+, which remain to be elucidated.
• BERGSTROM, D. E.;RUTH, J. L.
  作者：BERGSTROM, D. E.、RUTH, J. L.

  DOI：——

  日期：——
• C-5-Substituted pyrimidine nucleosides. 3. Reaction of allylic chlorides, alcohols, and acetates with pyrimidine nucleoside derived organopalladium intermediates
  作者：Donald E. Bergstrom、Jerry L. Ruth、Paul Warwick

  DOI：10.1021/jo00320a039

  日期：1981.3