1,2,3,4-tetrahydro-1-(2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-6-allylthymidyl)quinoline | 149204-07-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1,2,3,4-tetrahydro-1-(2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-6-allylthymidyl)quinoline
• 英文别名: 1,2,3,4-tetrahydro-1-[2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-6-allylthymidyl]quinoline；1-[(3aR,4R,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-(3,4-dihydro-2H-quinolin-1-ylmethyl)-6-prop-2-enylpyrimidine-2,4-dione
• CAS: 149204-07-9
• 化学式: C₃₁H₄₅N₃O₆Si
• 分子量: 583.8
• InChiKey: HQOUWXBWPADCOF-IYUNARRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  89.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydro-1-(2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-6-allylthymidyl)quinoline 以 正丁醇 为溶剂， 反应 0.42h， 以23%的产率得到(5R,6Z,8'R)-1,1'-bis[(3aR,4R,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-8'-ethenyl-6-prop-2-enylidenespiro[1,3-diazinane-5,7'-6,8-dihydro-5H-quinazoline]-2,2',4,4'-tetrone
  参考文献：
  名称：

  A chemical model for the fragmentation reaction in thymidylate synthase catalysis. Synthesis and evaluation of a 5-methylene-1-(1,2,3,4-tetrahydroquinolyl)-6-allyluridine

  摘要：

  Compounds 5 and 6 were synthesized as models to investigate the reactivity of proposed intermediate 2 in thymidylate synthase (TS) catalysis as it fragments to form dTMP. The mechanism of the fragmentation (homolytic or heterolytic) of model 6 was determined via subsequent interaction of the fragmented center with the C6 allyl substituent. The results were consistent with an ionic fragmentation of 6, followed by loss of an allylic proton, and subsequent thermal electrocyclic or Diels-Alder reactions of the resulting trienes 13 and 14, respectively. Independent generation of radicals analogous to that produced from a radical fragmentation of model 6 did not result in formation of trienes 13 and 14.

  DOI：

  10.1021/jo00062a014
• 作为产物：
  描述：

  1-(2',3'-O-isopropylidene-5'-O-tert-butyldimethylsilyl)-5-(formyl-dimethylacetal)-6-(3-propanal)-uridine 在 sodium tetrahydroborate 、 三丁基膦 、 双氧水 、 sodium cyanoborohydride 、 氯化铵 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 14.0h， 生成 1,2,3,4-tetrahydro-1-(2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-6-allylthymidyl)quinoline
  参考文献：
  名称：

  A chemical model for the fragmentation reaction in thymidylate synthase catalysis. Synthesis and evaluation of a 5-methylene-1-(1,2,3,4-tetrahydroquinolyl)-6-allyluridine

  摘要：

  Compounds 5 and 6 were synthesized as models to investigate the reactivity of proposed intermediate 2 in thymidylate synthase (TS) catalysis as it fragments to form dTMP. The mechanism of the fragmentation (homolytic or heterolytic) of model 6 was determined via subsequent interaction of the fragmented center with the C6 allyl substituent. The results were consistent with an ionic fragmentation of 6, followed by loss of an allylic proton, and subsequent thermal electrocyclic or Diels-Alder reactions of the resulting trienes 13 and 14, respectively. Independent generation of radicals analogous to that produced from a radical fragmentation of model 6 did not result in formation of trienes 13 and 14.

  DOI：

  10.1021/jo00062a014

文献信息

• A chemical model for the fragmentation reaction in thymidylate synthase catalysis. Synthesis and evaluation of a 5-methylene-1-(1,2,3,4-tetrahydroquinolyl)-6-allyluridine
  作者：John R. Kagel、Binghe Wang、Mathias P. Mertes

  DOI：10.1021/jo00062a014

  日期：1993.5

  Compounds 5 and 6 were synthesized as models to investigate the reactivity of proposed intermediate 2 in thymidylate synthase (TS) catalysis as it fragments to form dTMP. The mechanism of the fragmentation (homolytic or heterolytic) of model 6 was determined via subsequent interaction of the fragmented center with the C6 allyl substituent. The results were consistent with an ionic fragmentation of 6, followed by loss of an allylic proton, and subsequent thermal electrocyclic or Diels-Alder reactions of the resulting trienes 13 and 14, respectively. Independent generation of radicals analogous to that produced from a radical fragmentation of model 6 did not result in formation of trienes 13 and 14.