3-(1-Hydroxy-3-oxo-1,3-dihydro-isoindol-2-ylmethyl)-thiophene-2-carboxylic acid methyl ester | 203264-24-8

• 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: 3-(1-Hydroxy-3-oxo-1,3-dihydro-isoindol-2-ylmethyl)-thiophene-2-carboxylic acid methyl ester
• 英文别名: methyl 3-[(1-hydroxy-3-oxo-1H-isoindol-2-yl)methyl]thiophene-2-carboxylate
• CAS: 203264-24-8
• 化学式: C₁₅H₁₃NO₄S
• 分子量: 303.339
• InChiKey: QBHXUYRWJALPNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  95.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(1-Hydroxy-3-oxo-1,3-dihydro-isoindol-2-ylmethyl)-thiophene-2-carboxylic acid methyl ester 在 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 以92%的产率得到3-(1-Hydroxy-3-oxo-1,3-dihydro-isoindol-2-ylmethyl)-thiophene-2-carboxylic acid
  参考文献：
  名称：

  Selective access to N-aryl or N-alkyl derivatives of isoindolo[2,1-b][2,4]benzo(or thieno)diazepines

  摘要：

  N-alkyl isoindolo[2, 1-b][2,4]benzodiazepines 15c were synthesized via an intramolecular N-acyliminium ion-amide reaction, N-aryl derivatives 8c were obtained from an intramolecular acylation of amino acids 6c in acetic anhydride. A generalization of these methodologies is given in the synthesis of the thiophenic analogues 15d and 8d. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10359-3
• 作为产物：
  描述：

  Methyl 3-[(1,3-dioxoisoindol-2-yl)methyl]thiophene-2-carboxylate 在 盐酸 、 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 0.5h， 以94%的产率得到3-(1-Hydroxy-3-oxo-1,3-dihydro-isoindol-2-ylmethyl)-thiophene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Selective access to N-aryl or N-alkyl derivatives of isoindolo[2,1-b][2,4]benzo(or thieno)diazepines

  摘要：

  N-alkyl isoindolo[2, 1-b][2,4]benzodiazepines 15c were synthesized via an intramolecular N-acyliminium ion-amide reaction, N-aryl derivatives 8c were obtained from an intramolecular acylation of amino acids 6c in acetic anhydride. A generalization of these methodologies is given in the synthesis of the thiophenic analogues 15d and 8d. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10359-3

文献信息

• Thieno[2′,3′:5,6]azepino[2,1-<i>a</i>]isoindolones from hydroxylactam-alcohols<i>via N</i>-acyliminium ion olefin cyclization
  作者：Pascal Pigeon、Mohamed Othman、Bernard Decroix

  DOI：10.1002/jhet.5570380105

  日期：2001.1

  A one pot synthesis of thienoazepinoisoindolones from the reaction of hydroxylactam-alcohols, under acidic treatment, is described via an N-acyliminium olefin cyclization.

  通过N-酰亚胺基烯烃环化描述了在酸性处理下由羟基内酰胺-醇的反应进行的一锅合成噻吩并氮杂异吲哚酮。
• Study of a 1,6-hydride shift in an open chain of hydroxylactam-triarylcarbinols
  作者：Pascal Pigeon、Aı̈cha Mamouni、Jana Sikoraiova、Stefan Marchalin、Bernard Decroix

  DOI：10.1016/s0040-4020(01)00437-9

  日期：2001.6

  Hydroxylactam-alcohols 5a,b,d (isoindole series), under acidic treatment gave phthalimides 7a,b,d via a hydride shift induced by an intramolecular pi -stacking (benzene-benzene or benzene-thiophene interaction) which did not occur in 10a (succinimide series). (C) 2001 Elsevier Science Ltd. All rights reserved.
• Selective access to N-aryl or N-alkyl derivatives of isoindolo[2,1-b][2,4]benzo(or thieno)diazepines
  作者：Pascal Pigeon、Mohamed Othman、Pierre Netchitailo、Bernard Decroix

  DOI：10.1016/s0040-4020(97)10359-3

  日期：1998.2

  N-alkyl isoindolo[2, 1-b][2,4]benzodiazepines 15c were synthesized via an intramolecular N-acyliminium ion-amide reaction, N-aryl derivatives 8c were obtained from an intramolecular acylation of amino acids 6c in acetic anhydride. A generalization of these methodologies is given in the synthesis of the thiophenic analogues 15d and 8d. (C) 1998 Elsevier Science Ltd. All rights reserved.