Methyl 3-[(2-methylpropan-2-yl)oxycarbonyldiazenyl]pent-2-enoate | 1181674-74-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Methyl 3-[(2-methylpropan-2-yl)oxycarbonyldiazenyl]pent-2-enoate
• CAS: 1181674-74-7
• 化学式: C₁₁H₁₈N₂O₄
• 分子量: 242.275
• InChiKey: CKTFLZZPQDZPQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  77.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 3-[(2-methylpropan-2-yl)oxycarbonyldiazenyl]pent-2-enoate 在 sodium hydride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.17h， 生成 methyl 3-(4-chlorophenyl)-5-ethyl-1-phenyl-1H-pyrazole-4-carboxylate
  参考文献：
  名称：

  Divergent Construction of Pyrazoles via Michael Addition of N-Arylhydrazones to 1,2-Diaza-1,3-dienes

  摘要：

  The base (NaH)-promoted Michael addition of N-arylhydrazones (AHs) with 1,2-diaza-1,3-dienes (DDs) produces unprecedented beta-azohydrazone adducts. Strategically, the use of AHs as acyl anion equivalents (d(1) synthon) and DDs as a-electrophiles (a(2) synthon) of carbonyl compounds open the way to two important classes of pyrazole compounds

  DOI：

  10.1021/acs.orglett.5b00776

文献信息

• Direct Access to Variously Substituted 2-Imino-4-thiazolines
  作者：Stefania Santeusanio、Orazio Attanasi、Gianfranco Favi、Paolino Filippone、Francesca Perrulli

  DOI：10.1055/s-0030-1258108

  日期：2010.7

  1,2-Diaza-1,3-dienes readily react as Michael acceptors with thiocyanic acid generated in situ from potassium thiocyanate. The acidic medium of the reaction promotes the intramolecular ring closure of the α-thiocyanato hydrazones allowing access to novel 2-imino-4-thiazolines functionalized at positions 3, 4, and 5 in a one-pot, high-yielding process.

  1,2-二氮-1,3-二烯很容易作为Michael受体与原位生成的硫氰酸反应，该反应的酸性介质促进了α-硫氰酸脲的内环化闭合，从而实现了一锅法、高收率地合成在3、4和5位功能化的新的2-亚氨基-4-噻唑啉。
• Divergent Approach to Thiazolylidene Derivatives: A Perspective on the Synthesis of a Heterocyclic Skeleton from β-Amidothioamides Reactivity
  作者：Stefania Santeusanio、Roberta Majer、Francesca Romana Perrulli、Lucia De Crescentini、Gianfranco Favi、Gianluca Giorgi、Fabio Mantellini

  DOI：10.1021/acs.joc.7b02135

  日期：2017.9.15

  Herein we report a domino protocol able to reach regioselectively thiazolylidene systems by combining the reactive peculiarities of both β-amidothioamides (ATAs) and 1,2-diaza-1,3-dienes (DDs). Depending on the reaction conditions and/or the nature of the residue at C4 of the heterodiene system, ATAs can act as hetero-mononucleophiles or hetero-dinucleophiles in the diversified thiazolylidene ring

  本文中，我们报告了一种通过结合β-酰胺基硫酰胺（ATA）和1,2-二氮杂-1,3-二烯（DDs）的反应特性来达到区域选择性噻唑基亚胺体系的多米诺协议。取决于反应条件和/或杂二烯系统的C 4处的残基的性质，ATA可以充当多样化的噻唑基亚环组件中的杂单亲核试剂或杂二亲核试剂。
• Synthesis of novel symmetrical 2-oxo-spiro[indole-3,4′-pyridines] by a reaction of oxindoles with 1,2-diaza-1,3-dienes
  作者：Orazio A. Attanasi、Linda A. Campisi、Lucia De Crescentini、Gianfranco Favi、Fabio Mantellini

  DOI：10.1039/c4ob01959h

  日期：——

  Synthesis of symmetrical 2-oxo-spiro[indole-3,4′-pyridines]: a novel example of spirocyclic oxindoles bearing a quaternary centre at the 3-position.

  对称2-氧代螺[indole-3,4′-吡啶]的合成：一种在3位上带有季铵中心的螺环氧吲哚的新例子。
• Access to novel imidazo[1,5-a]pyrazine scaffolds by the combined use of a three-component reaction and a base-assisted intramolecular cyclization
  作者：Orazio A. Attanasi、Gianfranco Favi、Gianluca Giorgi、Roberta Majer、Francesca Romana Perrulli、Stefania Santeusanio

  DOI：10.1039/c4ob00676c

  日期：——

  A novel and practical two-step approach to an intriguing class of imidazo[1,5-a]pyrazines with exocyclic CX (X = CH2, O) bonds is described. The process utilizes a sequential three-component reaction of propargyl amine or aminoester, 1,2-diaza-1,3-dienes and isothiocyanates to furnish functionalized 2-thiohydantoins which are transformed into thiohydantoin-fused tetrahydropyrazines by subsequent regioselective

  描述了一种新颖实用的两步方法，用于合成具有环外C X（X = CH 2，O）键的咪唑并[1,5- a ]吡嗪类。该方法利用炔丙胺或氨基酯，1，2-二氮杂-1，3-二烯和异硫氰酸酯的三组分顺序反应来提供官能化的2-硫代乙内酰脲，其通过随后的区域选择性碱基促进的环化作用转化成硫代乙内酰脲-融合的四氢吡嗪。
• Metal and Oxidant-Free Brønsted Acid-Mediated Cascade Reaction to Substituted Benzofurans
  作者：Giacomo Mari、Cecilia Ciccolini、Lucia De Crescentini、Gianfranco Favi、Stefania Santeusanio、Michele Mancinelli、Fabio Mantellini

  DOI：10.1021/acs.joc.9b01363

  日期：2019.9.6

  Substituted hydroxy-benzofurans are easily accessible by treatment of resorcinols and 1,2-diaza-1,3-dienes (DDs) under acidic conditions. The reaction happens through an uncommon Michael reaction between aromatic derivatives as aromatic C(sp2)–H nucleophiles and DDs as acceptors. Also, the behavior of different phenols and 2-naphthol was investigated.

  通过在酸性条件下处理间苯二酚和1,2-二氮杂-1,3-二烯（DDs），可以轻松获得取代的羟基苯并呋喃。该反应通过芳香族衍生物（作为芳香族C（sp 2）–H亲核体）和DDs作为受体之间的罕见迈克尔反应而发生。此外，还研究了不同酚和2-萘酚的行为。