ethyl 2-diazo-3-carbonyl-4-phenylbutyrate | 188475-11-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-diazo-3-carbonyl-4-phenylbutyrate
• 英文别名: (E)-3-diazonio-4-ethoxy-4-oxo-1-phenylbut-2-en-2-olate
• CAS: 188475-11-8
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: YLMZZMRKBWCZPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  45.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-diazo-3-carbonyl-4-phenylbutyrate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 3-Aethoxycarbonyl-5-phenyl-4-hydroxypyrazol
  参考文献：
  名称：

  Discovery of novel hydroxy pyrazole based factor IXa inhibitor

  摘要：

  Synthesis and biological data of a novel selective and efficacious factor lXa inhibitor are described along with its crystal structure in factor VIIa. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.123
• 作为产物：
  描述：

  苯乙酰氯 在 吡啶 、 4-乙酰氨基苯磺酰叠氮 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 ethyl 2-diazo-3-carbonyl-4-phenylbutyrate
  参考文献：
  名称：

  [EN] HETEROCYCLIC COMPOUNDS AS FACTOR IXA INHIBITORS
  [FR] COMPOSÉS HÉTÉROCYCLIQUES EN TANT QU'INHIBITEURS DU FACTEUR IXA

  摘要：

  公开号：

  WO2009143039A3

文献信息

• Cu(I)-catalyzed reaction of diazo compounds with terminal alkynes: a direct synthesis of trisubstituted furans
  作者：Mohammad Lokman Hossain、Fei Ye、Yan Zhang、Jianbo Wang

  DOI：10.1016/j.tet.2014.07.086

  日期：2014.9

  method for the synthesis of tri-substituted furans has been developed based on Cu(I)-catalyzed reaction of terminal alkynes with β-keto α-diazoesters. This method for the synthesis of 2,3,5-trisubstituted furans is operationally simple and applicable to wide substrate scope. Moreover, this synthesis employs cheap Cu(MeCN)4PF6 as the catalyst and no additional ligand is needed. Similar reaction has also been

  基于Cu（I）催化的末端炔烃与β-酮α-重氮酸酯的反应，已经开发了一种三取代呋喃的合成方法。该合成2,3,5-三取代呋喃的方法操作简单，适用于广泛的底物范围。此外，该合成采用廉价的Cu（MeCN）4 PF 6作为催化剂，不需要其他配体。类似的反应也已用于（E）-2-重氮-3-（甲氧基亚氨基）丁酸乙酯，用于合成2,3,5-三取代的N-甲氧基吡咯，但效果有限。
• New Approaches to Polysubstituted Pyrroles and γ-Lactams Based on Nucleophilic Addition of Ti(IV) Enolates Derived from α-Diazo-β-keto Carbonyl Compounds to <i>N</i>-Tosylimines
  作者：Changqing Dong、Guisheng Deng、Jianbo Wang

  DOI：10.1021/jo0605039

  日期：2006.7.1

  The Ti(IV) enolates derived from α-diazo-β-keto esters or ketones efficiently add to TiCl4-activated N-tosylimines to give δ-N-tosylamino substituted α-diazo-β-keto carbonyl compounds. The diazo decomposition of the addition products occurs under Rh2(OAc)4-catalyzed or photoinduced conditions to afford pyrrole or γ-lactam derivatives, both in high yields.

  衍生自α-重氮-β-酮酯或酮的Ti（IV）烯醇化物有效地添加到TiCl 4活化的N-甲苯胺中，得到δ- N-甲苯磺酰基氨基取代的α-重氮-β-酮羰基化合物。加成产物的重氮分解在Rh 2（OAc）4催化或光诱导的条件下发生，以高产率提供吡咯或γ-内酰胺衍生物。
• Rhodium-catalyzed synthesis of 2,3 – Disubstituted N -methoxy pyrroles and furans via [3+2] cycloaddition between metal carbenoids and activated olefins
  作者：Bharath Kumar Kuruba、Samuel Vasanthkumar、Lourdusamy Emmanuvel

  DOI：10.1016/j.tet.2017.04.007

  日期：2017.6

  the synthesis of 2-substituted N-alkoxy pyrrole 3-carboxylate and furan 3-carboxylate via Rh-catalyzed [3+2] cycloaddition between α-diazo oxime ether or α-diazo carbonyl compounds with vinyl equivalents in a one-pot process. We have demonstrated ethyl vinyl ether as well as vinyl acetate as vinyl equivalents and both were found to give excellent yields. We have also demonstrated the synthesis of N-alkoxy

  我们首次报道了通过α-重氮肟醚或具有乙烯基当量的α-重氮羰基化合物之间的Rh催化的[3 + 2]环加成反应合成2-取代的N-烷氧基吡咯3-羧酸盐和呋喃3-羧酸盐在一锅法过程中。我们已经证明乙基乙烯基醚以及乙酸乙烯酯作为乙烯基当量，并且发现两者均具有优异的产率。我们还证明了通过在低温下进行反应可以合成N-烷氧基二氢吡咯衍生物。
• An efficient protocol for the synthesis of six-membered N, O-heterocycles via a 1,3-dipolar (3+3) cycloaddition between nitrile oxide and α-diazo esters
  作者：Bharath Kumar Kuruba、Samuel Vasanthkumar

  DOI：10.1016/j.tet.2017.05.055

  日期：2017.7

  In this manuscript, we are reporting an efficient protocol for the construction of highly functionalized N, O-heterocyclic derivatives such as 1,2,4-oxadiazine and 1,4,2-dioxazine-6-carboxylate derivatives via a 1,3-dipolar (3 + 3) cycloaddition between nitrile oxide and unprotected α-diazo esters in the presence of 2 mol% Cu(OTf)2 catalyst. The expected N, O-heterocycles were obtained in excellent

  在这份手稿中，我们报告了一种有效的方案，可通过1,3-构筑高度官能化的N，O-杂环衍生物，例如1,2,4-恶二嗪和1,4,2-二恶嗪-6-羧酸酯衍生物在2 mol％Cu（OTf）2催化剂存在下，丁腈与未保护的α-重氮酯之间进行偶极（3 + 3）环加成。以优异的产率获得了预期的N，O-杂环。已知这些N，O-杂环具有杀虫和杀螨特性。
• Tandem Cross‐Coupling/Spirocyclization/Mannich‐Type Reactions of 3‐(2‐Isocyanoethyl)indoles with Diazo Compounds toward Polycyclic Spiroindolines
  作者：Guo‐Shu Chen、Shu‐Jie Chen、Jian Luo、Xiang‐Yu Mao、Albert Sun‐Chi Chan、Raymond Wai‐Yin Sun、Yun‐Lin Liu

  DOI：10.1002/anie.201911614

  日期：2020.1.7

  and subsequent spirocyclization/Mannich-type reaction have been developed to assemble polycyclic spiroindoline skeletons. Formation of spiroindolenines has been proven as the crucial step for the following Mannich-type cyclization reaction. Accordingly, a novel approach on chiral phosphoric acid catalyzed Mannich-type cyclization toward the formation of diastereomerically and enantiomerically enriched

  已经开发了Pd催化的3-（2-异氰乙基）吲哚与重氮乙酸酯的交叉偶联串联反应，以及随后的螺环化/曼尼希型反应，以组装多环螺二氢吲哚骨架。螺环吲哚胺的形成已被证明是随后的曼尼希型环化反应的关键步骤。因此，已经建立了一种新的手性磷酸催化曼尼希型环化的方法，以形成非对映体和对映体富集的五环螺二氢吲哚啉。而且，该反应的产物是合成化学中的通用结构单元，如合成了aspasposperma和kopsia生物碱的关键构架所证明的那样。