2-phenylsulfanyl-acetoacetic acid ethyl ester | 27872-73-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-phenylsulfanyl-acetoacetic acid ethyl ester
• 英文别名: ethyl 3-oxo-2-phenylsulfanylbutanoate；α-Phenylthio-acetessigsaeure-aethylester；2-Phenylmercapto-acetessigsaeure-aethylester
• CAS: 27872-73-7
• 化学式: C₁₂H₁₄O₃S
• 分子量: 238.307
• InChiKey: BSVDROJBPIAHQN-UHFFFAOYSA-N

物化性质

• 沸点：
  169-170 °C(Press: 23 Torr)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-phenylsulfanyl-acetoacetic acid ethyl ester 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 ethyl (E)-3-phenylselanyl-2-phenylsulfanylbut-2-enoate
  参考文献：
  名称：

  Stereoselective synthesis of vinylic chalcogenides through vinylic substitution by lithium organylchalcogenolates

  摘要：

  Enol phosphates and enol tosilates of P-dicarbonyl compounds react with lithium organoselenolates to give beta-organo-seleno (Z) -alpha,beta-unsaturated carbonyl compounds. Tetrasubstituted vinylic vic-bis(organylchalcogenides) of (E)-geometry have been prepared by this method. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.074
• 作为产物：
  描述：

  Ethyl-α,α'-bis(phenylthio)acetoacetat 在 sodium ethanolate 、 乙硫醇钠 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以83%的产率得到2-phenylsulfanyl-acetoacetic acid ethyl ester
  参考文献：
  名称：

  关于控制碳上的亚磺酰基

  摘要：

  通过控制还原易得的双-磺基化产物，可以实现与吸电子基团相邻的碳上的受控单磺基化。

  DOI：

  10.1039/c39820001183

文献信息

• Electrophilic substitutions with the electrogenerated sulfenium cation R1-S+
  作者：Quang Tho Do、Driss Elothmani、Georges Le Guillanton

  DOI：10.1016/s0040-4039(98)00871-5

  日期：1998.6

  The sulfenium cation R1-S+ electrogenerated by oxidation of organic disulfides, reacts with phenols, aromatic ethers and ketones bearing an hydrogen atom in α position, to give alkyl (aryl) sulfanyl compounds.

  通过有机二硫化物的氧化而电生成的sulf阳离子R 1 -S +与酚，芳族醚和在α位带有氢原子的酮反应，得到烷基（芳基）硫烷基化合物。
• Synthesis of some novel bioactive 4-oxy/thio substituted-1H-pyrazol-5(4H)-ones via efficient cross-Claisen condensation
  作者：R. Venkat Ragavan、V. Vijayakumar、N. Suchetha Kumari

  DOI：10.1016/j.ejmech.2009.04.010

  日期：2009.10

  α-Oxy/thio substituted-β-keto esters were synthesized through an efficient cross-Claisen condensation of aryl oxy/thio acetic acid ethyl esters with acid chlorides, then it is converted in situ into 4-oxy/thio substituted-1H-pyrazol-5(4H)-ones by the addition of hydrazine or hydrazine derivatives and screened for their antibacterial, antifungal activities.

  α-氧/硫取代的β酮酯是通过一种有效的交叉克莱森缩合合成芳氧/硫代乙酸乙酯与酰氯，然后它被转换原位成-4-氧基/硫基取代的1 ħ -通过添加肼或肼衍生物生成吡唑-5（4 H）-并筛选其抗菌，抗真菌活性。
• Sulfenylation of Active Methylene Compounds with Sulfenamides
  作者：Takanobu Kumamoto、Susumu Kobayashi、Teruaki Mukaiyama

  DOI：10.1246/bcsj.45.866

  日期：1972.3

  secondary alkylamines with active methylene compounds afforded mono-sulfenylated compounds in good yields. The reactions of 2 mol of sulfenamides derived from imides with 1 mol of active methylene compounds in the presence of a base gave di-sulfenylated compounds. It was found that α-mono-sulfenylated ketones were prepared by the reactions of enamines with sulfenamides derived from imides. α-gem-Di-sulfenylated

  衍生自仲烷基胺的次磺酰胺与活性亚甲基化合物的等摩尔反应以良好的产率提供单次磺酰化的化合物。2 mol 衍生自酰亚胺的次磺酰胺与 1 mol 活性亚甲基化合物在碱存在下反应，得到二亚磺酰化化合物。发现α-单-亚磺酰化酮是通过烯胺与衍生自酰亚胺的次磺酰胺反应制备的。α-gem-Di-sulfenylated 酮是通过 α-mono-sulfenylated 酮与衍生自酰亚胺的亚磺酰胺在碱存在下反应制备的。还研究了N-苯基硫代苯甲脒盐酸盐的制备和反应。
• Alkylation of 4-(phenylthio)-1H-pyrazol-5-ols with methyl bromoacetate
  作者：R. N. Vydzhak、S. Ya. Panchishin、V. S. Brovarets

  DOI：10.1134/s107036321702013x

  日期：2017.2

  Alkylation of 4-(phenylthio)-1H-pyrazol-5-ols with methyl bromoacetate has afforded a series of phenyl pyrazolyl sulfides which have been oxidized into sulfones. The resulting esters have been hydrolyzed into the corresponding acids. The synthesized compounds potentially exhibit biological activity.

  4-（苯硫基）-1 H-吡唑-5-醇与溴乙酸甲酯的烷基化反应产生了一系列苯基吡唑基硫醚，已被氧化为砜。所得的酯已被水解成相应的酸。合成的化合物可能具有生物活性。
• Sodium Telluride-Mediated Sulfenylation of α-Halo Carbonyl Compounds with Diphenyl Disulfide
  作者：Seetharamaiyer Padmanabhan、Takuji Ogawa、Hitomi Suzuki

  DOI：10.1246/bcsj.62.1358

  日期：1989.4.15

  Under mild aprotic conditions α-halo carbonyl compounds react with diphenyl disulfide in the presence of sodium telluride to give the corresponding α-phenylthio derivatives in good to moderate yields. The reaction appears to proceed involving the sulfur–sulfur bond cleavage of diphenyl disulfide by sodium telluride.

  在温和的非质子惰性条件下，α-卤代羰基化合物在碲化钠存在下与二苯基二硫化物反应，以良好到中等的产率得到相应的 α-苯硫基衍生物。该反应似乎涉及碲化钠对二苯基二硫化物的硫-硫键裂解。