3-oxo-2-(thiophen-2-ylmethyl)-2,3-dihydro-1H-isoindole-1-carboxylic acid ethyl ester | 211430-91-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-oxo-2-(thiophen-2-ylmethyl)-2,3-dihydro-1H-isoindole-1-carboxylic acid ethyl ester
• 英文别名: ethyl 3-oxo-2-(thiophen-2-ylmethyl)-1H-isoindole-1-carboxylate
• CAS: 211430-91-0
• 化学式: C₁₆H₁₅NO₃S
• 分子量: 301.366
• InChiKey: IWFOPGSNNKTXID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-oxo-2-(thiophen-2-ylmethyl)-2,3-dihydro-1H-isoindole-1-carboxylic acid ethyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以80%的产率得到3-oxo-2-(thiophen-2-ylmethyl)-1H-isoindole-1-carboxylic acid
  参考文献：
  名称：

  New fused lactones from indolizinediones via N-acyliminium ions

  摘要：

  N-Arylmethylphthalimidine-3-carboxylates 3 are good precursors for the synthesis of ketones 5a,b or enols 6c-e which upon acidic treatment led to lactones 7 via an N-acyliminium ion. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00468-2
• 作为产物：
  描述：

  2-噻吩甲胺 、 diethyl α-bromohomophthalate 以 乙腈 为溶剂， 反应 8.0h， 生成 3-oxo-2-(thiophen-2-ylmethyl)-2,3-dihydro-1H-isoindole-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  Silver-catalyzed spirolactonization: first synthesis of spiroisoindole-γ-methylene-γ-butyrolactones

  摘要：

  gamma-Acetylenic carboxylic acids are cyclized to spirolactones under mild conditions, in the presence of Ag2CO3 catalyst. The corresponding spiro-5-alkylidene-gamma-butyrolactones were isolated in high yields, and this process constitutes an easy and efficient route to analogous structures of natural products of biological interest. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.137

文献信息

• Aza-heterocyclic frameworks through intramolecular π-system trapping of spiro-<i>N</i>-acyliminiums generated from isoindolinone
  作者：Sarra Chortani、Mohamed Othman、Ata Martin Lawson、Anis Romdhane、Hichem Ben Jannet、Michael Knorr、Lukas Brieger、Carsten Strohmann、Adam Daïch

  DOI：10.1039/d0nj04052e

  日期：——

  spiro-isoindolinone-imides. The latter were produced in large scale in three steps from homophthalic acid. These imides were useful to provide in one step isoindolinones bearing hydroxymethyl-amide functions, tethered at quaternary carbon centre with promising biological issues. Submitted to Brønsted (TFA neat) and Lewis acid (trimethylsilyltrifluoro-methanesulfonic (TMSOTf) 10 mol%), the spiro-acetoxylactams undergo

  通过螺-异吲哚满酮-酰亚胺的串联区域选择性还原/ O-酰化反应直接获得了作为主要底物的螺-乙酰氧基内酰胺。后者是由间苯二甲酸分三步大规模生产的。这些酰亚胺可用于一步提供具有羟甲基酰胺官能团的异吲哚啉酮，该化合物被季铵碳中心束缚，并具有潜在的生物学问题。螺-乙酰氧基内酰胺经Brønsted（TFA纯净）和路易斯酸（三甲基甲硅烷基三氟甲磺酸（TMSOTf）10摩尔％）进行π-环化N-酰基亚胺，非对映选择性地提供与芳族体系稠合或不稠合的π-芳族原始吡咯并吡咯并吡咯并氮杂庚烯-异吲哚。用π-烯烃，分离出与异吲哚啉融合或含有氨基酸的吡咯并吡啶和吡咯并-氮杂。还讨论了产生所有这些系统的反应机理。
• Halolactonization of g-Acetylenic Acids: Synthesis of Novel Spiroisoindole Halobutyrolactones
  作者：Mohamed Othman、Mohamed M. Rammah、Moncef Msaddek、Mohamed B. Rammah

  DOI：10.3987/com-08-11370

  日期：——
• A Convenient Synthesis of Novel Spiroisoindole γ-Halobutyrolactones via Halocyclization of γ-Ethylenic Acids
  作者：Mohamed Othman、Mohamed M. Rammah、Kabula Ciamala、Michael Knorr、Carsten Strohmann、Mohamed B. Rammah

  DOI：10.3987/com-09-11787

  日期：——

  gamma-Ethylenic carboxylic acids are cyclized to spirolsoindolone gamma-halomethylbutyrolactones, in the presence of NBS or NIS and K2CO3. The corresponding haloaspirobutyrolactones were isolated in high yields (57-95%).
• Silver-catalyzed spirolactonization: first synthesis of spiroisoindole-γ-methylene-γ-butyrolactones
  作者：Mohamed M. Rammah、Mohamed Othman、Kabula Ciamala、Carsten Strohmann、Mohamed B. Rammah

  DOI：10.1016/j.tet.2008.01.137

  日期：2008.4

  gamma-Acetylenic carboxylic acids are cyclized to spirolactones under mild conditions, in the presence of Ag2CO3 catalyst. The corresponding spiro-5-alkylidene-gamma-butyrolactones were isolated in high yields, and this process constitutes an easy and efficient route to analogous structures of natural products of biological interest. (c) 2008 Elsevier Ltd. All rights reserved.
• New fused lactones from indolizinediones via N-acyliminium ions
  作者：Mohamed Othman、Pascal Pigeon、Bernard Decroix

  DOI：10.1016/s0040-4020(98)00468-2

  日期：1998.7

  N-Arylmethylphthalimidine-3-carboxylates 3 are good precursors for the synthesis of ketones 5a,b or enols 6c-e which upon acidic treatment led to lactones 7 via an N-acyliminium ion. (C) 1998 Elsevier Science Ltd. All rights reserved.