ethyl (E)-2-hydrazono-3-benzylsulfinylpropionate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (E)-2-hydrazono-3-benzylsulfinylpropionate
• 英文别名: Ethyl 3-benzylsulfanyl-2-diazopropanoate；ethyl 3-benzylsulfanyl-2-diazopropanoate
• 化学式: C₁₂H₁₄N₂O₂S
• 分子量: 250.321
• InChiKey: PPABNCWTOLTTFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  53.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (E)-2-hydrazono-3-benzylsulfinylpropionate 在 氯化亚砜 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 ethyl 3-(benzylthio)-1H-indole-2-carboxylate
  参考文献：
  名称：

  通过衍生自α-氨基酸酯的重氮酯制备费歇尔吲哚合成的前体芳基azo的新方法

  摘要：

  描述了一种新颖的方法，该方法使用芳基锂试剂和容易从α-氨基酸酯获得的α-重氮酯来合成费歇尔吲哚合成的前体芳基hydr。

  DOI：

  10.1016/j.tetlet.2005.11.126

文献信息

• New Entry for Synthesis of N-Acylhydrazones, Pyridazinones, and 1,3,4-Oxadiazin-6-ones from .ALPHA.-Amino Acid Esters
  作者：Eiko Yasui、Masao Wada、Norio Takamura

  DOI：10.1248/cpb.55.1652

  日期：——

  Versatile electrophiles N-acylhydrazones are synthesized via diazotization, reduction, and acylation of α-amino acid esters. Reduction of diazo esters with L-selectride® or tributylphosphine affords the corresponding hydrazones in good yields. Both reducing agents give anti-hydrazones as the major product although the reactivity of each reductant is slightly different. The resulting hydrazones are acylated to give N-acylhydrazones, which are subjected to further reactions to give 1,3,4-oxadiazin-6-ones that serve as useful synthetic intermediates for the Diels–Alder reaction.

  通过对 α-氨基酸酯进行重氮化、还原和酰化，可合成多功能亲电体 N-酰肼。用 L-selectride® 或三丁基膦还原重氮酯，可以得到相应的肼，而且收率很高。尽管每种还原剂的反应性略有不同，但两种还原剂都会产生主要产物反肼。生成的肼经酰化后可得到 N-酰肼，再经进一步反应可得到 1,3,4-恶二嗪-6-酮，它们是 Diels-Alder 反应的有用合成中间体。
• Novel method for synthesis of aryl hydrazones from α-diazo esters: scope and limitations of nucleophiles
  作者：Eiko Yasui、Masao Wada、Norio Takamura

  DOI：10.1016/j.tet.2008.11.028

  日期：2009.1

  Aryl hydrazones, the precursor of Fischer indole synthesis, were easily obtained by nucleophilic addition of aryllithium reagents to diazo esters. The aryl hydrazones were converted into indoles in good yields by heating with thionyl chloride in alcohol. Grignard reagent was also a good nucleophile, whereas organozinc reagent did not react with diazo esters. Aryllithium reagents were prepared by reacting

  通过芳基锂试剂向重氮酯的亲核加成，很容易获得费歇尔吲哚合成的前体芳基hydr。通过与亚硫酰氯在醇中加热，将芳基酮以良好的产率转化为吲哚。格氏试剂也是良好的亲核试剂，而有机锌试剂则不会与重氮酯反应。芳基锂试剂是通过使在2-，3-，4-或多位具有各种取代基的芳基溴化物与n- BuLi反应制得的。将衍生自溴吡啶的亲核试剂加到重氮酯中也得到。
• A novel method for the synthesis of 3,4-disubstitutedpyrrole-2,5-dicarboxylates from hydrazones derived from α-diazo esters
  作者：Eiko Yasui、Masao Wada、Shinji Nagumo、Norio Takamura

  DOI：10.1016/j.tet.2013.03.037

  日期：2013.5

  Hydrazones obtained from alpha-diazo esters were converted to pyrroles when heated with thionyl chloride in alcohol. Among hydrazones, those substituted with a benzene ring on the beta-carbon to the ester are likely to give pyrroles in good yields. (C) 2013 Elsevier Ltd. All rights reserved.
• Novel approach to arylhydrazones, the precursor for Fischer indole synthesis, via diazo esters derived from α-amino acid esters
  作者：Eiko Yasui、Masao Wada、Norio Takamura

  DOI：10.1016/j.tetlet.2005.11.126

  日期：2006.1

  A novel method for synthesizing arylhydrazones, the precursor for Fischer indole synthesis, using aryllithium reagents and α-diazo esters that are easily obtained from α-amino acid esters, is described.

  描述了一种新颖的方法，该方法使用芳基锂试剂和容易从α-氨基酸酯获得的α-重氮酯来合成费歇尔吲哚合成的前体芳基hydr。