(E)-6-(phenylethenyl)-9-(O,O,O-tris(tert-butyldimethylsilyl)-α-D-ribofuranosyl)-9H-purine | 646522-20-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: (E)-6-(phenylethenyl)-9-(O,O,O-tris(tert-butyldimethylsilyl)-α-D-ribofuranosyl)-9H-purine
• CAS: 646522-20-5
• 化学式: C₃₆H₆₀N₄O₄Si₃
• 分子量: 697.153
• InChiKey: MXGVKKRPBQHFLN-ZJHHSWCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  47.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  80.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (E)-6-(phenylethenyl)-9-(O,O,O-tris(tert-butyldimethylsilyl)-α-D-ribofuranosyl)-9H-purine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以47%的产率得到trans-6-styryl-9β-D-ribofuranosyl-9H-purine
  参考文献：
  名称：

  Cytotoxic activity of 6-alkynyl- and 6-alkenylpurines

  摘要：

  6-Alkynyl- and 6-alkenylpurines have been screened for cytotoxic activity against a human chronic myelogenous leukemia cell line; K-562 cells using a [H-3]-thymidine incorporation assay. Most alkynes displayed cytotoxicity comparable to, or better than, the known anticancer drugs 6-mercaptopurine and fludarabine. The 6-alkenylpurines, which are promising plant growth stimulators and 15-lipoxygenase inhibitors, exhibited only low toxicity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00011-8
• 作为产物：
  描述：

  6-chloro-9-(2,3,5-tris-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl)-9H-purine 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium diacetate 、 N,N-二异丙基乙胺 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 (E)-6-(phenylethenyl)-9-(O,O,O-tris(tert-butyldimethylsilyl)-α-D-ribofuranosyl)-9H-purine
  参考文献：
  名称：

  Cytotoxic activity of 6-alkynyl- and 6-alkenylpurines

  摘要：

  6-Alkynyl- and 6-alkenylpurines have been screened for cytotoxic activity against a human chronic myelogenous leukemia cell line; K-562 cells using a [H-3]-thymidine incorporation assay. Most alkynes displayed cytotoxicity comparable to, or better than, the known anticancer drugs 6-mercaptopurine and fludarabine. The 6-alkenylpurines, which are promising plant growth stimulators and 15-lipoxygenase inhibitors, exhibited only low toxicity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00011-8

文献信息

• Synthesis of (E)-6-alkenylpurines via Pd-catalyzed stannation/protodestannation tandem process of alkynylpurines
  作者：Martin Klečka、Martin Křováček、Tomáš Tobrman、Dalimil Dvořák

  DOI：10.1135/cccc2009563

  日期：——

  A methodology for the synthesis of (E)-6-alkenylpurines, starting from 6-iodopurines, based on a Pd-catalyzed stannation/protodestannation protocol, is described. The alkynylation reactions were catalyzed by Pd(OAc)₂/PPh₃ in acetonitrile. The Pd-catalyzed stannation itself provided a mixture of Z regioisomers but following protodestannation using TFA induces Z to E isomerization giving (E)-6-alkenylpurines. The reactivity of other 2- and 8-alkynyl purines has also been studied.

  介绍了一种从6-碘嘌呤出发，基于Pd催化的锡化/脱锡化协议，合成（E）-6-烯基嘌呤的方法。炔基化反应在乙腈中由Pd（OAc）2 / PPh3催化。 Pd催化的锡化本身提供了混合的Z-异构体，但是使用TFA进行脱锡化后，引发了Z到E的异构化，从而得到（E）-6-烯基嘌呤。还研究了其他2-和8-炔基嘌呤的反应性。