methyl 5-methyl2-methylene-3-(tosylcarbamoyloxy)hexanoate | 1242576-91-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 5-methyl2-methylene-3-(tosylcarbamoyloxy)hexanoate
• CAS: 1242576-91-5
• 化学式: C₁₇H₂₃NO₆S
• 分子量: 369.439
• InChiKey: VOCXRPUYQMDBCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  98.77
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 5-methyl2-methylene-3-(tosylcarbamoyloxy)hexanoate 在 sodium hydride 、 N-碘代丁二酰亚胺 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 168.0h， 生成 methyl (4S*,5S*)-4-iodomethyl-5-isobutyl-2-oxo-3-tosyloxazolidine-4-carboxylate 、 methyl (4S*,5R*)-4-iodomethyl-5-isobutyl-2-oxo-3-tosyloxazolidine-4-carboxylate
  参考文献：
  名称：

  Diastereoselective functionalisation of Baylis–Hillman adducts: a convenient approach to α-methyl-α-amino acids

  摘要：

  The N-tosyl carbamates 4a-e, easily prepared starting from the Baylis-Hillman adducts 3a-e, underwent cyclization carried out with I-2/NIS in the presence of NaH, to give the corresponding 2-oxo-1,3-oxazolidines 5a-e in good yield and total stereoselection when the substituent at C-5 is Ar. After the removal of tosyl group, followed by the cleavage of the heterocyclic ring, the alpha-methyl-alpha-amino acids 8a,b and 10 were obtained in good yield as hydrochlorides.

  DOI：

  10.1007/s00726-009-0465-y
• 作为产物：
  描述：

  3-羟基-5-甲基-2-亚甲基己酸甲酯 、 对甲基苯磺酰异氰酸酯 以 二氯甲烷 为溶剂， 反应 0.5h， 以95%的产率得到methyl 5-methyl2-methylene-3-(tosylcarbamoyloxy)hexanoate
  参考文献：
  名称：

  Diastereoselective functionalisation of Baylis–Hillman adducts: a convenient approach to α-methyl-α-amino acids

  摘要：

  The N-tosyl carbamates 4a-e, easily prepared starting from the Baylis-Hillman adducts 3a-e, underwent cyclization carried out with I-2/NIS in the presence of NaH, to give the corresponding 2-oxo-1,3-oxazolidines 5a-e in good yield and total stereoselection when the substituent at C-5 is Ar. After the removal of tosyl group, followed by the cleavage of the heterocyclic ring, the alpha-methyl-alpha-amino acids 8a,b and 10 were obtained in good yield as hydrochlorides.

  DOI：

  10.1007/s00726-009-0465-y