2,3-dihydrothiazolo[2,3-a]isoindol-5(9bH)-one | 3037-14-7

• 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: 2,3-dihydrothiazolo[2,3-a]isoindol-5(9bH)-one
• 英文别名: 2,3-dihydro-9bH-thiazolo[2,3-a]isoindol-5-one；2,3-Dihydro-9bH-thiazolo[2,3-a]isoindol-5-on；5-Oxo-tetrahydro-thiazolo<2,3-a>isoindol；3,9b-dihydro-2H-[1,3]thiazolo[2,3-a]isoindol-5-one
• CAS: 3037-14-7
• 化学式: C₁₀H₉NOS
• 分子量: 191.254
• InChiKey: OIESDSVNGZMEPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯酐 在 甲醇 、 sodium tetrahydroborate 、 C₁₀H₁₉Cl₈IrO₂Sn₃ 、 三乙胺 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 37.0h， 生成 2,3-dihydrothiazolo[2,3-a]isoindol-5(9bH)-one
  参考文献：
  名称：

  N-酰基亚胺离子化学中的多金属铱锡（Ir-Sn 3）催化剂：通过分子内和分子间酰胺基烷基化反应合成3-取代的异吲哚满酮

  摘要：

  AbstractThe multimetallic iridium‐tritin (Ir‐Sn3) complex [Cp*Ir(SnCl3)2{SnCl2(H2O)2}] (1) proved to be a highly effective catalyst towards COH bond activation of γ‐hydroxylactams, leading to a nucleophilic substitution reaction known as the α‐amidoalkylation reaction. Catalyst 1 can be easily synthesized from the reaction of (pentamethylcyclocyclopentadienyl)iridium dichloride dimer {[Cp*IrCl2]2} and tin(II) dichloride (SnCl2). In terms of catalyst loading, reaction conditions and yields of the product formed, 1 is found to be superior compared to classical Lewis acid catalysts. Different carbon (arenes, heteroarenes, allyltrimethylsilane, 1,3‐dicarbonyls) and heteroatom (alcohols, thiols, amides and sulfonamides) nucleophiles have been successfully employed in the intramolecular and intermolecular alkylations, as well as in heterocyclization reactions. In the majority of cases good to excellent yields of 3‐substituted isoindolinones and 5‐substituted pyrrolidin‐2‐ones have been obtained. Besides, the reactions are also atom economical and salt free. It is proposed that the multimetallic Ir‐Sn3 catalyst behaves as a mild and selective Lewis acid to activate the γ‐hydroxylactam towards the formation of the N‐acyliminium ion; the latter being trapped by potent nucleophiles leading to the desired products.magnified image

  DOI：

  10.1002/adsc.201400234

文献信息

• A Dynamic Multicomponent Approach for One‐Pot Synthesis of 3‐Thioisoindolinones
  作者：Morakot Sakulsombat、Marcus Angelin、Rémi Caraballo、Olof Ramström

  DOI：10.1002/ijch.201200101

  日期：2013.2

  A dynamic multicomponent reaction concept has been successfully applied to the syntheses of 3‐thioisoindolinones and tricyclic γ‐lactams. The reactions were efficiently designed and operated in the absence of any catalyst under mild reaction conditions, resulting in the convenient variation of substituents on the N‐ and S‐positions of the target products.

  动态多组分反应概念已成功应用于3-硫代异吲哚满酮和三环γ-内酰胺的合成。在温和的反应条件下，在没有任何催化剂的情况下有效地设计和操作了反应，从而方便地改变了目标产物N和S位置上的取代基。
• Method of conjugating aminothiol containing molecules to vehicles
  申请人：D'Amico C. Derin

  公开号：US20060199812A1

  公开（公告）日：2006-09-07

  The present invention relates to a novel chemical process that provides novel vehicle derivatives that are exceptional 1,2- or 1,3-aminothiol specific reagents for conjugation to unprotected targeted compounds (e.g., polypeptides, peptides, or organic compounds) having or modified to have a 1,2- or 1,3 aminothiol group. The invention further relates to the methods of using novel water-soluble polymer derivatives and conjugates thereof.

  本发明涉及一种新型化学过程，提供了新型车载衍生物，这些衍生物是杰出的1,2-或1,3-氨基硫醇特异性试剂，可用于与未保护的靶向化合物（例如多肽，肽或有1,2-或1,3-氨基硫醇基团的有机化合物）结合。本发明还涉及使用新型水溶性聚合物衍生物及其共轭物的方法。
• Preparation of Thiazolidines and Related Compounds: Lactams and Lactamidines
  作者：G. L. Oliver、J. R. Dann、J. W. Gates

  DOI：10.1021/ja01536a045

  日期：1958.2
• Azomethine Chemistry. IV. Chemistry of Fused Thiazolidines^1,2
  作者：Richard G. Hiskey、Samuel J. Dominianni

  DOI：10.1021/jo01016a040

  日期：1965.5
• VERWENDUNG VON THIAZOLOISOINDOLINON-DERIVATEN ALS ANTIVIRALE ARZNEIMITTEL
  申请人：BOEHRINGER MANNHEIM GMBH

  公开号：EP0556245B1

  公开（公告）日：1995-01-25