ethyl 2-{[3-(4-bromophenyl)-3-oxopropanthioyl]amino}acetate | 881891-92-5

• 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-{[3-(4-bromophenyl)-3-oxopropanthioyl]amino}acetate
• 英文别名: Ethyl 2-[[3-(4-bromophenyl)-3-oxopropanethioyl]amino]acetate；ethyl 2-[[3-(4-bromophenyl)-3-oxopropanethioyl]amino]acetate
• CAS: 881891-92-5
• 化学式: C₁₃H₁₄BrNO₃S
• 分子量: 344.229
• InChiKey: MDBPZUAXTCPHBB-UHFFFAOYSA-N

物化性质

• 熔点：
  88-90 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  454.0±55.0 °C(Predicted)
• 密度：
  1.452±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  87.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-{[3-(4-bromophenyl)-3-oxopropanthioyl]amino}acetate 在 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 6.5h， 生成 ethyl 3-(4-bromophenyl)-5-(ethylsulfanyl)-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  An efficient synthesis of highly substituted pyrroles from β-oxodithiocarboxylates

  摘要：

  alpha-Oxoketene-N,S-acetals, prepared by the reaction of alkyl glycinate hydrochlorides with beta-oxodithiocarboxylates followed by alkylation, underwent cyclization in presence of chloromethyleneiminium salt derived from POCl3/DMF to afford alkyl-3-aryl-4-formyl-5-(alkylsulfanyl)-1H-pyrrole-2-carboxylates in excellent yields. Alkyl-3-aryl-5-(alkylsulfanyl)-1H-pyrrole-2-carboxylates were formed in moderate yields when the same N,S-acetals were treated with DBU. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.076
• 作为产物：
  描述：

  甘氨酸乙酯盐酸盐 、 S-methyl 3-oxo-3-(4-bromophenyl) propanedithioate 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以98%的产率得到ethyl 2-{[3-(4-bromophenyl)-3-oxopropanthioyl]amino}acetate
  参考文献：
  名称：

  An efficient synthesis of highly substituted pyrroles from β-oxodithiocarboxylates

  摘要：

  alpha-Oxoketene-N,S-acetals, prepared by the reaction of alkyl glycinate hydrochlorides with beta-oxodithiocarboxylates followed by alkylation, underwent cyclization in presence of chloromethyleneiminium salt derived from POCl3/DMF to afford alkyl-3-aryl-4-formyl-5-(alkylsulfanyl)-1H-pyrrole-2-carboxylates in excellent yields. Alkyl-3-aryl-5-(alkylsulfanyl)-1H-pyrrole-2-carboxylates were formed in moderate yields when the same N,S-acetals were treated with DBU. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.076

文献信息

• Microwave assisted one-pot synthesis of pyrrolo[2,1-<i>b</i>]thiazol-6-ones from α-aroyl ketene-<i>N</i>,<i>S</i>-acetals
  作者：Paulson Mathew、M. Prasidha、C. V. Asokan

  DOI：10.1002/jhet.334

  日期：——

  α‐Aroyl ketene‐N,S‐acetals 3 prepared by the reaction of β‐oxothioamides 1 with phenacyl bromides 2, underwent sequential cyclizations under microwave irradiation to afford pyrrolo[2,1‐b]thiazol‐6‐ones 6 in good yields. A double cyclization takes place regioselectively in one pot and variety of functionalized pyrrolo[2,1‐b]thiazol‐6‐ones were prepared by this protocol. The mode of cyclization under

  由β-氧代硫代酰胺1与苯甲酰溴2反应制得的α-芳基酮烯N，S缩醛3在微波辐射下依次环化生成吡咯并[2,1 - b ]噻唑-6-酮6，收率高。在一个锅中区域选择性地进行双环化，并根据该方案制备了多种功能化的吡咯并[2,1-b]噻唑-6-酮。微波条件下的环化方式与常规加热不同。J.杂环化​​学。（2010）。
• Application of Functionalized<i>N</i>,<i>S</i>-Ketene Acetals-Microwave-Assisted Three-Component Domino Reaction for Rapid Direct Access to Imidazo[1,2-<i>a</i>]pyridines
  作者：Ming Li、Tengfei Li、Kelong Zhao、Mingda Wang、Lirong Wen

  DOI：10.1002/cjoc.201300252

  日期：2013.8

  Imidazo[1,2‐a]pyridines have been successfully synthesized in moderate to good yields via a tandem three‐component reaction of ethyl 2‐(3‐oxo‐3‐arylpropanethioamido)acetates with aromatic aldehydes and malononitrile by means of microwave irradiation using DABCO as the catalyst. The advantages of this method including high chemo‐ and regioselectivity make this new strategy highly attractive.

  咪唑并[1,2- a ]吡啶已成功合成，其中2-（3-氧代-3-3-芳基丙烷硫代酰胺基）乙酸乙酯与芳族醛和丙二腈通过微波辐射的串联三组分反应以中等至良好的收率合成。 DABCO作为催化剂。这种方法的优势包括高的化学选择性和区域选择性，使这种新策略极具吸引力。
• An efficient synthesis of highly substituted pyrroles from β-oxodithiocarboxylates
  作者：Paulson Mathew、C.V. Asokan

  DOI：10.1016/j.tet.2005.11.076

  日期：2006.2

  alpha-Oxoketene-N,S-acetals, prepared by the reaction of alkyl glycinate hydrochlorides with beta-oxodithiocarboxylates followed by alkylation, underwent cyclization in presence of chloromethyleneiminium salt derived from POCl3/DMF to afford alkyl-3-aryl-4-formyl-5-(alkylsulfanyl)-1H-pyrrole-2-carboxylates in excellent yields. Alkyl-3-aryl-5-(alkylsulfanyl)-1H-pyrrole-2-carboxylates were formed in moderate yields when the same N,S-acetals were treated with DBU. (c) 2005 Elsevier Ltd. All rights reserved.