methyl 3-([6-(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)hexyl]thio)-2-(iodomethyl)-2-methylpropanoate | 500005-28-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: methyl 3-([6-(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)hexyl]thio)-2-(iodomethyl)-2-methylpropanoate
• 英文别名: methyl 3-{[6-(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)hexyl]thio}-2-(iodomethyl)-2-methylpropanoate；methyl 3-[6-(2-amino-6-oxo-1H-purin-9-yl)hexylsulfanyl]-2-(iodomethyl)-2-methyl-3-oxopropanoate
• CAS: 500005-28-7
• 化学式: C₁₇H₂₄IN₅O₄S
• 分子量: 521.379
• InChiKey: WCXOAXIODQQWCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  154
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3-([6-(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)hexyl]thio)-2-(iodomethyl)-2-methylpropanoate 在 heptamethyl cob(I)yrinate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以92%的产率得到O-methyl-S-(1-9H-guanine-6-hexyl)-3-methylmonothiosuccinate
  参考文献：
  名称：

  在辅酶B12依赖的甲基丙二酰辅酶A突变酶的模型中，Co（I）诱导了甲基丙二酰-琥珀酰重排。

  摘要：

  发现2-溴甲基-2-甲基单硫代丙二酸酯重排成琥珀酰基衍生物是在存在一摩尔当量的Co（I）的情况下以定量收率发生的，所述Co（I）是通过用NaBH 4还原七甲基Co（II）亚氨酸盐高氯酸盐或电化学还原而生成的。手性硫代丙二酸酯产生外消旋琥珀酸酯。

  DOI：

  10.1039/b305782h
• 作为产物：
  描述：

  3-甲基-2-甲基丙二酸-1-叔丁基酯 在 甲酸 、 氯化亚砜 、 sodium hydride 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 7.58h， 生成 methyl 3-([6-(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)hexyl]thio)-2-(iodomethyl)-2-methylpropanoate
  参考文献：
  名称：

  摘要：

  The vitamin-B-12 derivative 11, incorporating a peripheral N-4-acetylcytosine moiety, was alkylated under, guanine reductive conditions with 2-(iodomethyl)-2-methylmonothiomalonate 8 bearing the complementary moiety. The reaction yielded a mixture of vitamin-B-12-derived complexes with variations in the cytosine moiety: products 16-18 with a cytosine, a N-4-acetylated cytosine and a N-4-acetylated reduced cytosine moiety were formed (see Scheme 5). The complexes were photolyzed in CHCl3/MeCN to yield the dimethylmalonate derivative 22 (Scheme 6) but not the rearranged succinate, in contrast to the results obtained earlier with complexes incorporating the A(.)T base pair (see Scheme 1).

  DOI：

  10.1002/1522-2675(200209)85:9<3002::aid-hlca3002>3.0.co;2-b

文献信息

• The Co(i) induced methylmalonyl-succinyl rearrangement in a model for the coenzyme B12 dependent methylmalonyl-CoA mutase
  作者：Fangping Sun、Tamis Darbre

  DOI：10.1039/b305782h

  日期：——

  The rearrangement of 2-bromomethyl-2-methylmonothiomalonates to succinyl derivatives was found to take place in quantitative yields in the presence of one molar equivalent of Co(I) generated by the reduction of heptamethyl Co(II)yrinate perchlorate with NaBH4 or electrochemically. The chiral thiomalonate gave racemic succinate.

  发现2-溴甲基-2-甲基单硫代丙二酸酯重排成琥珀酰基衍生物是在存在一摩尔当量的Co（I）的情况下以定量收率发生的，所述Co（I）是通过用NaBH 4还原七甲基Co（II）亚氨酸盐高氯酸盐或电化学还原而生成的。手性硫代丙二酸酯产生外消旋琥珀酸酯。
• ——
  作者：Fang-Ping Sun、Tamis Darbre

  DOI：10.1002/1522-2675(200209)85:9<3002::aid-hlca3002>3.0.co;2-b

  日期：2002.9

  The vitamin-B-12 derivative 11, incorporating a peripheral N-4-acetylcytosine moiety, was alkylated under, guanine reductive conditions with 2-(iodomethyl)-2-methylmonothiomalonate 8 bearing the complementary moiety. The reaction yielded a mixture of vitamin-B-12-derived complexes with variations in the cytosine moiety: products 16-18 with a cytosine, a N-4-acetylated cytosine and a N-4-acetylated reduced cytosine moiety were formed (see Scheme 5). The complexes were photolyzed in CHCl3/MeCN to yield the dimethylmalonate derivative 22 (Scheme 6) but not the rearranged succinate, in contrast to the results obtained earlier with complexes incorporating the A(.)T base pair (see Scheme 1).