(3R,4R)-methyl 1-oxo-3-(thiophen-2-y)isochroman-4-carboxylate | 1370022-03-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (3R,4R)-methyl 1-oxo-3-(thiophen-2-y)isochroman-4-carboxylate
• 英文别名: methyl 1-oxo-3-(thiophen-2-yl)isochroman-4-carboxylate；(3R,4R)-methyl 1-oxo-3-(thiophen-2-yl)isochroman-4-carboxylate；methyl (3R,4R)-1-oxo-3-thiophen-2-yl-3,4-dihydroisochromene-4-carboxylate
• CAS: 1370022-03-9
• 化学式: C₁₅H₁₂O₄S
• 分子量: 288.324
• InChiKey: VFCOTEAZYPSWGN-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  邻羧基苯乙酸 在 乙酸酐 、 N,N-二异丙基乙胺 、 三甲基硅烷化重氮甲烷 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 22.33h， 生成 (3R,4R)-methyl 1-oxo-3-(thiophen-2-y)isochroman-4-carboxylate 、 methyl 1-oxo-3-(thiophen-2-yl)isochroman-4-carboxylate
  参考文献：
  名称：

  醛与烯醇化酸酐之间的催化不对称环加成反应：顺式-选择性二氢异香豆素形成

  摘要：

  在三苯甲基取代的金鸡纳生物碱基催化剂的存在下，高邻苯二甲酸，芳基琥珀酸和戊二酸酐衍生物与芳族和脂族醛反应生成顺式内酯，其最高90:10 dr和99％ee。DFT研究表明，催化剂如何独特地带来与通常观察到的相反的非对映控制感。

  DOI：

  10.1021/acs.joc.8b02332

文献信息

• ENANTIOSELECTIVE ORGANIC ANHYDRIDE REACTIONS
  申请人：Connon Stephen J.

  公开号：US20130245268A1

  公开（公告）日：2013-09-19

  Disclosed herein is enantioselective synthetic method comprising reacting an enolisable C 4 -C 50 organic anhydride with a second compound selected from the group consisting of an aldehyde, a ketone, an aldimine, a ketimine or a Michael Acceptor in the presence of a bifunctional organocatalyst. The reaction may find particular utility in the enantioselective synthesis of medicinally relevant heterocycles, such as dihydroisocoumarins and dihydroisoquinolinones.

  本文披露了一种对映选择性合成方法，包括在双功能有机催化剂存在下，将可形成烯醇的C4-C50有机酐与来自醛、酮、醛亚胺、酮亚胺或迈克尔受体的第二化合物反应。该反应可能在对映选择性合成药用相关杂环化合物方面具有特殊的实用性，例如二氢异香豆素和二氢异喹啉酮。
• A Catalytic Asymmetric Reaction Involving Enolizable Anhydrides
  作者：Claudio Cornaggia、Francesco Manoni、Esther Torrente、Sean Tallon、Stephen J. Connon

  DOI：10.1021/ol300453s

  日期：2012.4.6

  In the presence of a highly efficient novel bifunctional organocatalyst at low loadings under mild conditions, enolizable homophthalic anhydrides can be added to a range of aromatic and aliphatic aldehydes to give dihydroisocoumarins, with excellent yields and diastereo- and enantiocontrol (up to 99% ee).
• cis/trans-Isochromanones. DMAP induced cycloaddition of homophthalic anhydride and aldehydes
  作者：Milen G Bogdanov、Mariana D Palamareva

  DOI：10.1016/j.tet.2004.01.040

  日期：2004.3

  Homophthalic anhydride (1) reacts with wide variety of aromatic aldehydes, in the presence of chloroform and DMAP (N,N-dimethyl-4-amino-pyridine) at room temperature, to give in high yields cis- and trans-1-oxo-isochroman-4-carboxylic acids. Under these conditions, the trans-isomer is predominant and formation of Perkin-type products was not observed in contrast to the reaction carried out in the presence of pyridine. The unexpected trans-6-oxo-11-thiophen-2-yl-11,12-dihydro-6H-dibenzo[c,h]chromene-12-carboxylic acid methyl ester (8) was isolated when the reaction between 1 and thiophene-2-carbaldehyde was carried out in pyridine. (C) 2004 Elsevier Ltd. All rights reserved.
• US9050586B2
  申请人：——

  公开号：US9050586B2

  公开（公告）日：2015-06-09
• Catalytic Asymmetric Cycloadditions between Aldehydes and Enolizable Anhydrides: <i>cis</i>-Selective Dihydroisocoumarin Formation
  作者：Maria Luisa Aiello、Umar Farid、Cristina Trujillo、Brendan Twamley、Stephen J. Connon

  DOI：10.1021/acs.joc.8b02332

  日期：2018.12.21

  In the presence of a trityl-substituted cinchona alkaloid-based catalyst, homophthalic, aryl succinic, and glutaconic anhydride derivatives reacted with aromatic and aliphatic aldehydes to produce cis-lactones in up to 90:10 dr and 99% ee. A DFT study has shown how the catalyst is uniquely able to bring about the opposite sense of diastereocontrol to that usually observed.

  在三苯甲基取代的金鸡纳生物碱基催化剂的存在下，高邻苯二甲酸，芳基琥珀酸和戊二酸酐衍生物与芳族和脂族醛反应生成顺式内酯，其最高90:10 dr和99％ee。DFT研究表明，催化剂如何独特地带来与通常观察到的相反的非对映控制感。