3-(phenylthio)pentane-2,4-dione | 22805-23-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(phenylthio)pentane-2,4-dione
• 英文别名: 2,4-Pentanedione, 3-(phenylthio)-；3-phenylsulfanylpentane-2,4-dione
• CAS: 22805-23-8
• 化学式: C₁₁H₁₂O₂S
• 分子量: 208.281
• InChiKey: CKFBAZZEGYDMJV-UHFFFAOYSA-N

物化性质

• 沸点：
  47 °C(Press: 0.001 Torr)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(phenylthio)pentane-2,4-dione 在 四氯化钛 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 92.0h， 生成 ethyl 4,6-dimethyl-3-ethyl-5-(phenylthio)salicylate
  参考文献：
  名称：

  Regioselective synthesis of diaryl sulfides by [3+3] cyclizations of 1,3-bis(trimethylsilyloxy)-1,3-dienes

  摘要：

  Functionalized and sterically encumbered diaryl sulfides were prepared based on [3+3] cyclizations of 1,3-bis(trimethylsityloxy)-1,3-dienes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.01.150
• 作为产物：
  描述：

  3,3-bis(phenylthio)-2,4-pentanedione 在 四丁基硫酸氢铵 作用下， 以 乙腈 为溶剂， 以66%的产率得到3-(phenylthio)pentane-2,4-dione
  参考文献：
  名称：

  Electroreductive cleavage of carbon-sulphur bonds in dithioacetals

  摘要：

  DOI：

  10.1016/s0040-4020(01)81653-7

文献信息

• KI-catalyzed C–S bond formation <i>via</i> an oxidation relay strategy: efficient access to various α-thio-β-dicarbonyl compounds
  作者：Yi Jiang、Jiao-Xia Zou、Long-Tao Huang、Xue Peng、Jie-Dan Deng、Long-Qing Zhu、Yu-Hang Yang、Yi-Yue Feng、Xiao-Yun Zhang、Zhen Wang

  DOI：10.1039/c8ob00080h

  日期：——

  An efficient and practical methodology to obtain α-thio-β-dicarbonyl compounds was presented under alkaline conditions via potassium iodide (KI) catalysis.

  在碱性条件下，通过碘化钾（KI）催化，提出了一种获得α-硫代-β-二羰基化合物的高效实用方法。
• Synthesis of functionalized diaryl sulfides based on regioselective one-pot cyclizations of 1,3-bis(trimethylsilyloxy)-1,3-butadienes
  作者：Muhammad A. Rashid、Nasir Rasool、Muhammad Adeel、Helmut Reinke、Christine Fischer、Peter Langer

  DOI：10.1016/j.tet.2008.02.010

  日期：2008.4

  Functionalized diaryl sulfides were prepared based on one-pot cyclizations of 1,3-bis(trimethylsilyloxy)-1,3-butadienes.

  基于1，3-双（三甲基甲硅烷氧基）-1，3-丁二烯的一锅法环化制备官能化的二芳基硫醚。
• 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。
• K₂S₂O₈/I₂promoted syntheses of α-thio-β-dicarbonyl compounds via oxidative C–S coupling reactions under transition metal-free and solvent-free conditions
  作者：Yi-Wei Liu、Satpal Singh Badsara、Yi-Chen Liu、Chin-Fa Lee

  DOI：10.1039/c5ra07204b

  日期：——

  K₂S₂O₈/I₂promoted C–S coupling reaction of β-diketone with disulfide has been described. The resulting α-thio-β-diketones compounds were obtained in good to excellent yields.

  K₂S₂O₈/I₂促进了β-二酮与二硫化物的C-S偶联反应。得到的α-硫代β-二酮化合物产率良好至优异。
• Regioselective Mono- and Bis-Sulfenylation of Active Methylene Compounds
  作者：Namita Devi、Rajjakfur Rahaman、Kuladip Sarma、Pranjit Barman

  DOI：10.1002/ejoc.201501148

  日期：2016.1

  Selective mono- and bis-sulfenylation of active methylene groups with a variety of disulfides at an ambient temperature is reported. Sulfenylation is promoted by iodine as a catalyst and sulfenyl iodides as intermediates, under metal-free conditions. The method is greener in terms of solvent selection and the use of less hazardous DMSO as an oxidant. The procedure is highly efficient with readily available

  据报道，在环境温度下，活性亚甲基与多种二硫化物的选择性单-和双-亚磺酰化反应。在无金属条件下，以碘为催化剂，以亚硫基碘为中间体，可促进亚磺酰化。该方法在溶剂选择和使用危害较小的 DMSO 作为氧化剂方面更环保。该程序非常有效，使用容易获得的起始材料，并提供良好的收率。

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