5-oxo-2,3,5,8b-tetrahydrothiazolo[2,3-a]isoindole-3-carboxylic acid | 615288-51-2

• 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: 5-oxo-2,3,5,8b-tetrahydrothiazolo[2,3-a]isoindole-3-carboxylic acid
• 英文别名: (3R,9bS)-5-oxo-2,3,5,9b-tetrahydrothiazolo[2,3-a]isoindole-3-carboxylic acid；(3R,9bS)-5-oxo-3,9b-dihydro-2H-[1,3]thiazolo[2,3-a]isoindole-3-carboxylic acid
• CAS: 615288-51-2
• 化学式: C₁₁H₉NO₃S
• 分子量: 235.263
• InChiKey: IXPPKDOOVXQPGI-WPRPVWTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-oxo-2,3,5,8b-tetrahydrothiazolo[2,3-a]isoindole-3-carboxylic acid 在 乙酸酐 作用下， 反应 4.0h， 以37%的产率得到3-methylene-2,5-dioxo-3H,9bH-oxazolo[2,3-a]isoindole
  参考文献：
  名称：

  Synthesis of tricyclic isoindoles and thiazolo[3,2-c][1,3]benzoxazines

  摘要：

  The thermolysis of (3R,9bS)-5-oxo-2,3,5,9b-tetrahydrothiazolo[2,3-a]isoindole-3-carboxylic acids in Ac2O led to novel 3-methylene-2.5-dioxo-3H,9bH-oxazolo[2,3-a]isoindoles and chiral (9bS)-5-oxo-2,3,5,9b-tetrahydrothiazolo[2,3-a]isoindoles were obtained on FVP. Starting from L-cysteine methyl ester (3R,10bR)-5-oxo-2,3-dihydro-10bH-[1.3]thiazolo[3,2-c][1,3]benzoxazines were obtained as single stereoisomers. The thermolysis of (3R,10bR)-5-oxo-2,3-dihydro- 10bH-[1.3]thiazolo[3,2-c][1,3]benzoxazine-3-carboxylic acid in Ac2O cave 5-acetyl-2-phenyl-2,3-dihydrothiazole. The structures of methyl (3R,9bS)-5-oxo-2,3,5,9b-tetrahydrothiazolo[2,3-a]isoindole-3-carboxylate la and methyl (2R,4R)-N-chlorocarbonyl-2-(2-hydroxyphenyl)thiazolidine-4-carboxylate 9 were determined by X-ray crystallography. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.030
• 作为产物：
  描述：

  methyl (3R,9bS)-5-oxo-2,3,5,9b-tetrahydrothiazolo[2,3-a]isoindole-3-carboxylate 在 lithium iodide 、 盐酸 作用下， 以 乙酸乙酯 为溶剂， 以91%的产率得到5-oxo-2,3,5,8b-tetrahydrothiazolo[2,3-a]isoindole-3-carboxylic acid
  参考文献：
  名称：

  新型三环异吲哚衍生物的合成

  摘要：

  （3 R，9b S）-5-oxo-2,3,5，（3 R，9b S）-5-oxo-2,3,5的热解反应制得了新型3-亚甲基-2,5-二氧代-3 H，9b H-恶唑并[2,3- a ]异吲哚。乙酸酐中的9b-四氢噻唑并[2,3- a ]异吲哚-3-羧酸。通过X射线晶体学测定3-亚甲基-2，5-二氧代-3 H，9b H-恶唑并[2，3- a ]异吲哚6a的结构。

  DOI：

  10.1016/j.tetlet.2003.09.065

文献信息

• Synthesis of novel tricyclic isoindole derivatives
  作者：Teresa M.V.D. Pinho e Melo、Catarina I.A. Santos、António M.d'A. Rocha Gonsalves、José A. Paixão、Ana M. Beja、Manuela Ramos Silva

  DOI：10.1016/j.tetlet.2003.09.065

  日期：2003.11

  Novel 3-methylene-2,5-dioxo-3H,9bH-oxazolo[2,3-a]isoindoles were prepared from the thermolysis of (3R,9bS)-5-oxo-2,3,5,9b-tetrahydrothiazolo[2,3-a]isoindole-3-carboxylic acids in acetic anhydride. The structure of 3-methylene-2,5-dioxo-3H,9bH-oxazolo[2,3-a]isoindole 6a was determined by X-ray crystallography.

  （3 R，9b S）-5-oxo-2,3,5，（3 R，9b S）-5-oxo-2,3,5的热解反应制得了新型3-亚甲基-2,5-二氧代-3 H，9b H-恶唑并[2,3- a ]异吲哚。乙酸酐中的9b-四氢噻唑并[2,3- a ]异吲哚-3-羧酸。通过X射线晶体学测定3-亚甲基-2，5-二氧代-3 H，9b H-恶唑并[2，3- a ]异吲哚6a的结构。
• Synthesis of tricyclic isoindoles and thiazolo[3,2-c][1,3]benzoxazines
  作者：Teresa M.V.D Pinho e Melo、Catarina I.A Santos、António M.d'A Rocha Gonsalves、José A Paixão、Ana M Beja

  DOI：10.1016/j.tet.2004.03.030

  日期：2004.4

  The thermolysis of (3R,9bS)-5-oxo-2,3,5,9b-tetrahydrothiazolo[2,3-a]isoindole-3-carboxylic acids in Ac2O led to novel 3-methylene-2.5-dioxo-3H,9bH-oxazolo[2,3-a]isoindoles and chiral (9bS)-5-oxo-2,3,5,9b-tetrahydrothiazolo[2,3-a]isoindoles were obtained on FVP. Starting from L-cysteine methyl ester (3R,10bR)-5-oxo-2,3-dihydro-10bH-[1.3]thiazolo[3,2-c][1,3]benzoxazines were obtained as single stereoisomers. The thermolysis of (3R,10bR)-5-oxo-2,3-dihydro- 10bH-[1.3]thiazolo[3,2-c][1,3]benzoxazine-3-carboxylic acid in Ac2O cave 5-acetyl-2-phenyl-2,3-dihydrothiazole. The structures of methyl (3R,9bS)-5-oxo-2,3,5,9b-tetrahydrothiazolo[2,3-a]isoindole-3-carboxylate la and methyl (2R,4R)-N-chlorocarbonyl-2-(2-hydroxyphenyl)thiazolidine-4-carboxylate 9 were determined by X-ray crystallography. (C) 2004 Elsevier Ltd. All rights reserved.