1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-(2,2-dibromoethenyl)oxolan-2-yl]-3-[(4-methoxyphenyl)methoxymethyl]pyrimidine-2,4-dione | 223637-86-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-(2,2-dibromoethenyl)oxolan-2-yl]-3-[(4-methoxyphenyl)methoxymethyl]pyrimidine-2,4-dione
• CAS: 223637-86-3
• 化学式: C₂₅H₃₄Br₂N₂O₆Si
• 分子量: 646.448
• InChiKey: DJKIZTQFBIVZKF-ZRCGQRJVSA-N

物化性质

• 沸点：
  606.725±65.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.459±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  77.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-(2,2-dibromoethenyl)oxolan-2-yl]-3-[(4-methoxyphenyl)methoxymethyl]pyrimidine-2,4-dione 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(3-hydroxy-prop-1-ynyl)-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyloxymethyl)-5-triethylsilanylethynyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Exploitation of an unexpectedin situ heteroaromatic bromination for the synthesis of a porphyrin functionalized nucleoside

  摘要：

  A 2'-deoxyuridine derivative functionalized via an acetylenic junction with a Zn(II) tetraarylporphyrin has been prepared. Is also reported an unexpected in situ bromination of the uracil nucleic base at the C5 position, which occurs during the transformation of a dibromo-olefin into its corresponding acetylenic anion. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00483-9
• 作为产物：
  描述：

  3',5'-O-di(tert-butyldimethylsilyl)-2'-deoxyuridine 在 草酰氯 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 37.5h， 生成 1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-(2,2-dibromoethenyl)oxolan-2-yl]-3-[(4-methoxyphenyl)methoxymethyl]pyrimidine-2,4-dione
  参考文献：
  名称：

  Exploitation of an unexpectedin situ heteroaromatic bromination for the synthesis of a porphyrin functionalized nucleoside

  摘要：

  A 2'-deoxyuridine derivative functionalized via an acetylenic junction with a Zn(II) tetraarylporphyrin has been prepared. Is also reported an unexpected in situ bromination of the uracil nucleic base at the C5 position, which occurs during the transformation of a dibromo-olefin into its corresponding acetylenic anion. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00483-9

文献信息

• Exploitation of an unexpectedin situ heteroaromatic bromination for the synthesis of a porphyrin functionalized nucleoside
  作者：Nathalie Solladie´、Maurice Gross

  DOI：10.1016/s0040-4039(99)00483-9

  日期：1999.4

  A 2'-deoxyuridine derivative functionalized via an acetylenic junction with a Zn(II) tetraarylporphyrin has been prepared. Is also reported an unexpected in situ bromination of the uracil nucleic base at the C5 position, which occurs during the transformation of a dibromo-olefin into its corresponding acetylenic anion. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.