(2-chloropyridin-3-yl)bis-[2-(methylsulfanyl)pyrimidin-4-yl]methyl acetate | 488150-23-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2-chloropyridin-3-yl)bis-[2-(methylsulfanyl)pyrimidin-4-yl]methyl acetate
• 英文别名: [(2-Chloropyridin-3-yl)-bis(2-methylsulfanylpyrimidin-4-yl)methyl] acetate
• CAS: 488150-23-8
• 化学式: C₁₈H₁₆ClN₅O₂S₂
• 分子量: 433.942
• InChiKey: GWAMWADCVFTMLI-UHFFFAOYSA-N

物化性质

• 熔点：
  58-61 °C
• 沸点：
  609.6±50.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2-chloropyridin-3-yl)bis-[2-(methylsulfanyl)pyrimidin-4-yl]methyl acetate 在 三乙基硅烷 、 三氟甲磺酸 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 氯仿 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 147.5h， 生成 Deoxyvariolin B
  参考文献：
  名称：

  Concise Total Syntheses of Variolin B and Deoxyvariolin B

  摘要：

  The total synthesis of the marine alkaloid variolin B has been achieved in 8 steps and 17% overall yield, starting from commercially available 4-chloro-2-methylthiopyrimidine. The key reaction involves the tandem deoxygenation and cyclization of a triarylmethanol using a combination of triethylsilane and trifluoroacetic acid. In addition, the deoxygenated analogue was prepared in 6 steps and 23% overall yield, starting from the same starting material.

  DOI：

  10.1021/jo050523v
• 作为产物：
  描述：

  2-甲硫基-4-氯嘧啶 在 正丁基锂 、 氢碘酸 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 18.0h， 生成 (2-chloropyridin-3-yl)bis-[2-(methylsulfanyl)pyrimidin-4-yl]methyl acetate
  参考文献：
  名称：

  Concise Total Syntheses of Variolin B and Deoxyvariolin B

  摘要：

  The total synthesis of the marine alkaloid variolin B has been achieved in 8 steps and 17% overall yield, starting from commercially available 4-chloro-2-methylthiopyrimidine. The key reaction involves the tandem deoxygenation and cyclization of a triarylmethanol using a combination of triethylsilane and trifluoroacetic acid. In addition, the deoxygenated analogue was prepared in 6 steps and 23% overall yield, starting from the same starting material.

  DOI：

  10.1021/jo050523v

文献信息

• VARIOLIN DERIVATIVES AND THEIR USE AS ANTITUMOR AGENTS
  申请人：Remuinan Modesto

  公开号：US20090197901A1

  公开（公告）日：2009-08-06

  Variolin derivatives of formula (5) are provided, wherein the substituent groups defined by X 2 , R 1 , R 2 , R 3 , R 6 , R 7 , and R 12 are each independently selected from the group consisting of H, OH, OR′, SH, SR′, SOR′, SO 2 R′, NO 2 , NH 2 , NHR′, N(R′) 2 , NHCOR′, NHSO 2 R′, CN, halogen, ═O, C(═O)H, C(═O)R′, CO 2 H, CO 2 R′, carboxyalkyl, C 1 -C 12 alkyl, C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted aralkyl and substituted or unsubstituted heteroaromatic; wherein each of the R′ groups is independently selected from the group consisting of H, OH, SH, NO 2 , NH 2 , CN, halogen, ═O, C(═O)H, C(═O)CH 3 , CO 2 H, CO 2 CH 3 , C 1 -C 12 alkyl, C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, aryl, aralkyl and heteroaromatic; wherein the pairs of groups of R 1 and R 2 , R 2 and R 3 , R 3 and R 12 , R 12 and R 6 , or R 6 and R 7 may be joined into a carbocyclic or heterocyclic ring system.
• US7495000B2
  申请人：——

  公开号：US7495000B2

  公开（公告）日：2009-02-24
• US7772241B2
  申请人：——

  公开号：US7772241B2

  公开（公告）日：2010-08-10