2-(Phthalimidylmethyl)thiazole-4-carboxylic acid methyl ester | 1044196-75-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(Phthalimidylmethyl)thiazole-4-carboxylic acid methyl ester
• 英文别名: methyl 2-[(1,3-dioxoisoindol-2-yl)methyl]-1,3-thiazole-4-carboxylate
• CAS: 1044196-75-9
• 化学式: C₁₄H₁₀N₂O₄S
• 分子量: 302.31
• InChiKey: YNTQXXCLUMESES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(Phthalimidylmethyl)thiazole-4-carboxylic acid methyl ester 在 盐酸 作用下， 以 水 、 丙酮 为溶剂， 反应 48.0h， 以55%的产率得到N-phthaloylmethyl-1,3-thiazole-4-carboxylic acid
  参考文献：
  名称：

  The synthesis, N-alkylation and epimerisation study of a phthaloyl derived thiazolidine

  摘要：

  The synthesis of the phthaloyl protected thiazolidine, N-phthaloyl-methyl-2(R)-thiazolidine-4(R)-methyl ester, 2, and a study of its susceptibility to epimerise in a range of solvents, using H-1 NMR spectroscopy, are described. Compound 2 was further reacted to yield the thiazole amino acid derivative, 3, and an N-alkylated thiazolidine derivative, 6, as a single diastereoisomer. The N-alkylation of 2, using mild bases, resulted in the formation of a mixture of diastereoisomers of 2 (2R,4R) and (2S,4R). Successful cleavage of the methyl ester and the phthaloyl protecting groups was achieved, giving rise to the formation of the two heterocyclic building blocks, 4 and 5. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.097
• 作为产物：
  描述：

  N-phthaloylmethyl-2(R)-1,3-thiazolidine-4(R)-carboxylic acid methyl ester 在 吡啶 、 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 120.0h， 以63%的产率得到2-(Phthalimidylmethyl)thiazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  The synthesis, N-alkylation and epimerisation study of a phthaloyl derived thiazolidine

  摘要：

  The synthesis of the phthaloyl protected thiazolidine, N-phthaloyl-methyl-2(R)-thiazolidine-4(R)-methyl ester, 2, and a study of its susceptibility to epimerise in a range of solvents, using H-1 NMR spectroscopy, are described. Compound 2 was further reacted to yield the thiazole amino acid derivative, 3, and an N-alkylated thiazolidine derivative, 6, as a single diastereoisomer. The N-alkylation of 2, using mild bases, resulted in the formation of a mixture of diastereoisomers of 2 (2R,4R) and (2S,4R). Successful cleavage of the methyl ester and the phthaloyl protecting groups was achieved, giving rise to the formation of the two heterocyclic building blocks, 4 and 5. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.097

文献信息

• The synthesis, N-alkylation and epimerisation study of a phthaloyl derived thiazolidine
  作者：Emma B. Veale、John E. O'Brien、Thomas McCabe、Thorfinnur Gunnlaugsson

  DOI：10.1016/j.tet.2008.04.097

  日期：2008.7

  The synthesis of the phthaloyl protected thiazolidine, N-phthaloyl-methyl-2(R)-thiazolidine-4(R)-methyl ester, 2, and a study of its susceptibility to epimerise in a range of solvents, using H-1 NMR spectroscopy, are described. Compound 2 was further reacted to yield the thiazole amino acid derivative, 3, and an N-alkylated thiazolidine derivative, 6, as a single diastereoisomer. The N-alkylation of 2, using mild bases, resulted in the formation of a mixture of diastereoisomers of 2 (2R,4R) and (2S,4R). Successful cleavage of the methyl ester and the phthaloyl protecting groups was achieved, giving rise to the formation of the two heterocyclic building blocks, 4 and 5. (c) 2008 Elsevier Ltd. All rights reserved.