2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pent-4-enoic acid chloride | 916049-18-8

• 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: 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pent-4-enoic acid chloride
• CAS: 916049-18-8
• 化学式: C₁₃H₁₀ClNO₃
• 分子量: 263.68
• InChiKey: JJHWSUOYZZBNSZ-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  54.45
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pent-4-enoic acid chloride 在 palladium on activated charcoal 氢气 、 碳酸氢钠 、 臭氧 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 生成 methyl (1S,7S)-7-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-8-oxohexahydro-1H-pyrazolo[1,2-a]pyridazine-1-carboxylate
  参考文献：
  名称：

  Constrained peptidomimetics: building bicyclic analogs of pyrazoline derivatives

  摘要：

  A synthetic route has been developed for incorporating pyrazoline derivatives as proline surrogates in constrained X-Pro peptidomimetics. The route allows for the synthesis of dipeptide building blocks having either a six or seven-membered-ring annulated onto the pyrazoline moiety, as well as for the asymmetric synthesis of analogs having substituents on N-terminal side of the building block. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.027
• 作为产物：
  描述：

  N-乙氧羰基邻苯二甲酰亚胺 在 五氯化磷 、 sodium carbonate 作用下， 以 乙醚 、 水 为溶剂， 反应 2.0h， 生成 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pent-4-enoic acid chloride
  参考文献：
  名称：

  Building Functionalized Peptidomimetics:  Use of Electroauxiliaries for Introducing N-Acyliminium Ions into Peptides

  摘要：

  A series of silyl-substituted amino acids have been synthesized, inserted into peptides, and then employed as precursors for oxidatively generating reactive N-acyliminium ions. Both electrochemical and chemical oxidation procedures have been employed. N-Acyliminium ion generation in a solid-phase substrate as well as application to a small library of functionalized dipeptides has been demonstrated. Limitations in terms of how electron-rich the silyl groups can be as well as the compatibility of multiple silyl groups within a longer peptide are defined.

  DOI：

  10.1021/ja064737l

文献信息

• Tridentate Directing Groups Stabilize 6-Membered Palladacycles in Catalytic Alkene Hydrofunctionalization
  作者：Miriam L. O’Duill、Rei Matsuura、Yanyan Wang、Joshua L. Turnbull、John A. Gurak、De-Wei Gao、Gang Lu、Peng Liu、Keary M. Engle

  DOI：10.1021/jacs.7b08383

  日期：2017.11.8

  Removable tridentate directing groups inspired by pincer ligands have been designed to stabilize otherwise kinetically and thermodynamically disfavored 6-membered alkyl palladacycle intermediates. This family of directing groups enables regioselective remote hydrocarbofunctionalization of several synthetically useful alkene-containing substrate classes, including 4-pentenoic acids, allylic alcohols, homoallyl amines, and bis-homoallylamiries, under Pd(II) catalysis. In conjunction with previous findings, we demonstrate regiodivergent hydro-functionalization of 34Dutenoic acid derivatives to afford either Markovnikov or anti-Markovnikov addition products depending on directing group choice. Preliminary mechanistic and computational data are presented to support the proposed catalytic cycle.
• [EN] TETRAPEPTIDE ANALOGS<br/>[FR] ANALOGUES DE TETRAPEPTIDE
  申请人：IDUN PHARMACEUTICALS INC

  公开号：WO2006017295A3

  公开（公告）日：2007-07-12
• Stereodefined Access to Lactams via Olefin Difunctionalization: Iridium Nitrenoids as a Motif of LUMO-Controlled Dipoles
  作者：Seung Youn Hong、Sukbok Chang

  DOI：10.1021/jacs.9b04317

  日期：2019.7.3

  Reported herein is a general platform of a stereodefined access to gamma-lactams via Cp*Ir-catalyzed olefin difunctionalization, where in situ generated Ir-nitrenoid is utilized as a key motif of 1,3-dipoles to enable amido transfer in a syn-selective manner. Computational studies suggested that the stereodefined process can be attributed to the proposed working mode of concerted [3 + 2] cyclization. Frontier molecular orbital (FMO) analysis implied that a low-lying lowest unoccupied molecular orbital (LUMO) of the Ir-imido fragment engages in the olefin interaction. Mechanistic understanding on the nitrene transfer process led us to develop mild catalytic protocols of stereoselective difunctionalization of alkenyl dioxazolones to furnish alpha-(haloalkyl)- or (oxyalkyl)lactam products which are of high synthetic and medicinal utility. Product stereochemistry (threo and erythro) was found to be designated by the olefin geometry (E/Z) of substrates.