3-(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-ylmethylsulfanyl)-propionic acid methyl ester | 750597-65-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-ylmethylsulfanyl)-propionic acid methyl ester
• CAS: 750597-65-0
• 化学式: C₁₅H₂₁NO₄S
• 分子量: 311.402
• InChiKey: HKXAHSJAHVVGHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  57.65
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-ylmethylsulfanyl)-propionic acid methyl ester 在 盐酸 、 manganese(IV) oxide 、 sodium hydroxide 、 对甲苯磺酸 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 红铝 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 39.0h， 生成 4-dimethoxymethyl-5-(3-dimethylamino-propylsulfanylmethyl)-2-methyl-pyridin-3-ol
  参考文献：
  名称：

  Polymeric and dendrimeric pyridoxal enzyme mimics

  摘要：

  Pyridoxal was covalently attached to polyethylenimine polymers, but the resulting materials were found to degrade rapidly. In comparison, the dendrimeric pyridoxals, which possess only one pyridoxal unit at the core of every dendrimer molecule were found to be relatively stable compounds. A total of 12 poly(amidoamine) type dendrimers were synthesized. They range from G1 to G6 with either NMe2 or NHAc termini. The NMe2-terminated pyridoxal dendrimers racemize alpha-amino acids 50-100 times faster than does simple pyridoxal, while the NHAc-terminated pyridoxal dendrimers racemize alpha-amino acids only 3-5 times faster than does simple pyridoxal. Both the NMe2- and NHAc-terminated pyridoxal dendrimers decarboxylate 2-amino-2-phenyl-propionic acid 1-3 times faster than simple pyridoxal. The interior polarity in the pyridoxal dendrimers is similar to that of 85:15 water-DMFsolution. Furthermore we successfully incorporated eight lauryl groups to the G5 pyridoxal dendrimer at known positions. The laurylated dendrimer exhibits lower racemization and decarboxylation rates than do the unlaurylated ones, in contrast to the positive rate effects of laurylation in polyethylenimine-pyridoxamines in our previous transamination studies. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.03.062
• 作为产物：
  描述：

  2,2,8-三甲基-4H-1,3-二恶英并[4,5-c]吡啶-5-甲醇 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.33h， 生成 3-(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-ylmethylsulfanyl)-propionic acid methyl ester
  参考文献：
  名称：

  Polymeric and dendrimeric pyridoxal enzyme mimics

  摘要：

  Pyridoxal was covalently attached to polyethylenimine polymers, but the resulting materials were found to degrade rapidly. In comparison, the dendrimeric pyridoxals, which possess only one pyridoxal unit at the core of every dendrimer molecule were found to be relatively stable compounds. A total of 12 poly(amidoamine) type dendrimers were synthesized. They range from G1 to G6 with either NMe2 or NHAc termini. The NMe2-terminated pyridoxal dendrimers racemize alpha-amino acids 50-100 times faster than does simple pyridoxal, while the NHAc-terminated pyridoxal dendrimers racemize alpha-amino acids only 3-5 times faster than does simple pyridoxal. Both the NMe2- and NHAc-terminated pyridoxal dendrimers decarboxylate 2-amino-2-phenyl-propionic acid 1-3 times faster than simple pyridoxal. The interior polarity in the pyridoxal dendrimers is similar to that of 85:15 water-DMFsolution. Furthermore we successfully incorporated eight lauryl groups to the G5 pyridoxal dendrimer at known positions. The laurylated dendrimer exhibits lower racemization and decarboxylation rates than do the unlaurylated ones, in contrast to the positive rate effects of laurylation in polyethylenimine-pyridoxamines in our previous transamination studies. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.03.062