ethyl 2-{[(Z)3-(4-chlorophenyl)-3-hydroxy-2-propene-1-thione]amino}acetate | 843640-83-5

• 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-{[(Z)3-(4-chlorophenyl)-3-hydroxy-2-propene-1-thione]amino}acetate
• 英文别名: ethyl 2-{[3-(4-chlorophenyl)-3-oxopropanthioyl]amino}acetate；Ethyl 2-[[3-(4-chlorophenyl)-3-oxopropanethioyl]amino]acetate
• CAS: 843640-83-5
• 化学式: C₁₃H₁₄ClNO₃S
• 分子量: 299.778
• InChiKey: IAMUJBVVMUNXAW-UHFFFAOYSA-N

物化性质

• 熔点：
  87-88 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  437.2±55.0 °C(Predicted)
• 密度：
  1.288±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-{[(Z)3-(4-chlorophenyl)-3-hydroxy-2-propene-1-thione]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-chlorophenyl)-5-(methylsulfanyl)-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：

  对氯苯乙酮 在 sodium hydride 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 ethyl 2-{[(Z)3-(4-chlorophenyl)-3-hydroxy-2-propene-1-thione]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

• Crystal structure, FT-IR, FT-Raman, 1H NMR and computational study of ethyl 2-{[(Z)3-(4-chlorophenyl)-3-hydroxy-2-propene-1-thione] amino} acetate
  作者：S. Prasanth、Mary Varughese、Nirmala Joseph、Paulson Mathew、T.K. Manojkumar、C. Sudarsanakumar

  DOI：10.1016/j.molstruc.2014.10.037

  日期：2015.2

  Abstract The molecular structure of a thioamide derivative ethyl 2-[( Z )3-(4-chlorophenyl)-3-hydroxy-2-propene-1-thione] amino} acetate was determined by X-ray diffraction. The proton NMR ( 1 H NMR), Fourier Transform Infra-Red (FT-IR) and Fourier Transform Raman (FT-Raman) spectra of the compound were recorded and analyzed. The conjugated enol form of the compound was crystallized in the monoclinic

  摘要 通过X射线衍射确定了硫代酰胺衍生物乙基2-[(Z)3-(4-氯苯基)-3-羟基-2-丙烯-1-硫酮]氨基}乙酸乙酯的分子结构。记录并分析了该化合物的质子核磁共振（ 1 H NMR）、傅里叶变换红外（FT-IR）和傅里叶变换拉曼（FT-Raman）光谱。该化合物的共轭烯醇形式在单斜空间群 P2 1 /c 中结晶，晶胞尺寸 a = 12.514(2) A, b = 5.403(5) A, c = 21.233(3) A, β = 94.597 (4)°。结构通过直接方法求解并精制至 R 值为 0.0462。化合物中的硫代酰胺部分采用 Z 构象，CN 键显示出高旋转势垒。使用Gaussian 09程序通过B3LYP和RHF量子力学计算优化气相中的几何形状并计算振动频率。实验数据和理论数据吻合良好。
• 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。
• Cyclization of functionalized ketene-N,S-acetals to substituted pyrroles: applications in the synthesis of marine pyrrole alkaloids
  作者：Paulson Mathew、C.V. Asokan

  DOI：10.1016/j.tetlet.2004.11.076

  日期：2005.1

  alpha-Oxoketene-N,S-acetals, prepared by the reaction of alkyl glycinates with beta-oxodithiocarboxylates followed by alkylation, underwent cyclization in the presence of the Vilsmeier reagent to afford alkyl 3-aryl-4-formyl-5-(alkylsulfanyl)-1H-pyrrole-2-carboxylates in excellent yields. When the reaction was extended to beta-oxodithiocarboxylates derived from deoxyanision. 3,4-diarylpyrrole-2-carboxylates, the key intermediates in the synthesis of lukianol A and lamellarin Q were formed. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.