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ethyl 2-isocyanopent-4-enoate | 166655-28-3

中文名称
——
中文别名
——
英文名称
ethyl 2-isocyanopent-4-enoate
英文别名
——
ethyl 2-isocyanopent-4-enoate化学式
CAS
166655-28-3
化学式
C8H11NO2
mdl
MFCD11223679
分子量
153.181
InChiKey
GRYAVDXORXMSEO-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    1.5
  • 重原子数:
    11
  • 可旋转键数:
    5
  • 环数:
    0.0
  • sp3杂化的碳原子比例:
    0.5
  • 拓扑面积:
    30.7
  • 氢给体数:
    0
  • 氢受体数:
    3

反应信息

  • 作为反应物:
    描述:
    ethyl 2-isocyanopent-4-enoateGrubbs catalyst first generation lithium hydroxide 、 sodium hydroxide 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺三氟乙酸 作用下, 以 四氢呋喃乙醇二氯甲烷 为溶剂, 反应 113.0h, 生成
    参考文献:
    名称:
    Application of tandem Ugi multi-component reaction/ring closing metathesis to the synthesis of a conformationally restricted cyclic pentapeptide
    摘要:
    一种构象受限的环状五肽,含有不饱和的 9 元内酰胺作为半刚性支架,通过串联乌基反应/闭环偏析,以非常趋同的方式制备出来。
    DOI:
    10.1039/b414374d
  • 作为产物:
    描述:
    参考文献:
    名称:
    Thiol Mediated Free Radical Cyclization of Alkenyl and Alkynyl Isocyanides
    摘要:
    Thiol-mediated free radical cyclizations of but-3-enyl and but-3-ynyl isocyanides of types 6-8 give new access to 3,5-disubstituted 2-(alkyl- and 2-(arylthio)pyrrolines 11, 12, and 18. When 2-mercaptoethanol is used with the same isocyanides the reaction results in pyroglutamates 16, 17, or 19. These cyclizations involve the formation of a new carbon-carbon bond through intramolecular addition of a carbon-centered thioimidoyl radical to a carbon-carbon multiple bond. Although cyclic products are usually obtained in high yields, in a few cases a competing radical degradation process leading to isothiocyanates was observed. Isocyanide 8a carrying an allyl(phenyl) sulfide moiety isomerizes to 2-(phenylthio)pyrroline 24 in a series of sequential steps.
    DOI:
    10.1021/jo00104a035
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文献信息

  • Intramolecular Imidoylative Heck Reaction: Synthesis of Cyclic Ketoimines from Functionalized Isocyanide
    作者:Jian Wang、Shi Tang、Qiang Zhu
    DOI:10.1021/acs.orglett.6b01174
    日期:2016.7.1
    Efficient access to five- to seven-membered cyclic ketoimines, through palladium-catalyzed intramolecular imidoylative Heck reaction of alkene-containing isocyanides, has been developed. Consecutive isocyanide and alkene insertion into aryl or alkyl Pd(II) intermediates takes place in this process. No byproduct derived from monoinsertion or reversed sequence is detected.
    已经开发出通过催化含烯烃异氰酸酯的分子内酰亚胺化Heck反应,可以有效地获得五元至七元环状酮亚胺。在此过程中,异氰酸酯和烯烃连续插入芳基或烷基Pd(II)中间体中。没有检测到源自单插入或反向序列的副产物。
  • Application of tandem Ugi reaction/ring-closing metathesis in multicomponent synthesis of unsaturated nine-membered lactams
    作者:Luca Banfi、Andrea Basso、Giuseppe Guanti、Renata Riva
    DOI:10.1016/j.tetlet.2003.08.027
    日期:2003.10
    A new straightforward entry into unsaturated nine-membered lactams of potential use as external reverse turn inducers was developed. It is based on an Ugi multicomponent reaction using two unsaturated substrates, followed by highly stereoselective ring-closing metathesis (RCM). The synthesis of a nine-membered secondary lactam by RCM is reported for the first time.
    已经开发出一种新的直接进入不饱和九元内酰胺的方法,该内酰胺可能用作外部反向转导诱导剂。它基于使用两个不饱和底物的Ugi多组分反应,然后进行高度立体选择性的闭环复分解(RCM)。首次报道了通过RCM合成九元仲内酰胺。
  • Constrained Phenylalanine Derivatives by Enyne Metathesis and Diels−Alder Reaction
    作者:Sambasivarao Kotha、Nampally Sreenivasachary、Enugurthi Brahmachary
    DOI:10.1002/1099-0690(200102)2001:4<787::aid-ejoc787>3.0.co;2-n
    日期:2001.2
    approach for the synthesis of indane-based α-amino acid derivatives is reported. In this regard, the synthesis of five-membered exocyclic and five-membered inner-outer ring diene building blocks (7 and 15) containing α-amino acid moieties is described. Diene 15 is prepared by an enyne metathesis reaction as a key step. In this paper, a full account of our work regarding the Diels-Alder reaction of these dienes
    报道了一种合成基于茚满α-氨基酸生物的概念性新方法。在这方面,描述了含有 α-氨基酸部分的五元环外和五元内外环二烯结构单元(7 和 15)的合成。二烯 15 是通过烯炔复分解反应作为关键步骤制备的。在本文中,我们全面介绍了我们关于这些二烯与各种亲二烯体的 Diels-Alder 反应的工作,以及随后环加合物氧化得到各种茚满α-氨基酸生物的工作。
  • Microwave-assisted synthesis of γ-thiolactams from ethyl isocyanoacetate
    作者:Massimiliano Lamberto
    DOI:10.1515/hc-2018-0005
    日期:2018.6.27
    Abstract γ-Thiolactams were synthesized in good yields from ethyl isocyanoacetate through a sequential alkylation/isothiocyanation/radical cyclization under microwave irradiation.
    摘要 以异氰乙酸乙酯为原料,在微波辐照下通过连续烷基化/异化/自由基环化反应合成了γ-酰胺类化合物,收率良好。
  • Synthesis of constrained α-amino acid derivatives via enyne metathesis reaction
    作者:Sambasivarao Kotha、Nampally Sreenivasachary、Enugurthi Brahmachary
    DOI:10.1016/s0040-4039(98)00251-2
    日期:1998.4
    Synthesis of a diene building block via enyne metathesis reaction and its usage in the preparation of constrained alpha-amino acid derivatives is described. (C) 1998 Elsevier Science Ltd. All rights reserved.
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