methyl 2-(p-toluenesulfonyl)propanate | 86453-11-4

• 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: methyl 2-(p-toluenesulfonyl)propanate
• 英文别名: methyl (4-tolylsulfonyl)propionate；(±)-methyl 2-tosylpropanoate；Methyl 2-(4-methylphenyl)sulfonylpropanoate
• CAS: 86453-11-4
• 化学式: C₁₁H₁₄O₄S
• 分子量: 242.296
• InChiKey: DFPPXCBRJRTYAW-UHFFFAOYSA-N

物化性质

• 熔点：
  49-52 °C
• 沸点：
  170-171 °C(Press: 0.001 Torr)
• 密度：
  1.2228 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-(p-toluenesulfonyl)propanate 在 双氧水 、 四氯化锡 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 methyl r-1-(p-toluenesulfonyl)-c-2-[(phenylseleno)(trimethylsilyl)methyl]-1-cyclopropanecarboxylate
  参考文献：
  名称：

  [2 + 1] Cycloaddition Reactions of a 1-Seleno-2-silylethene to 2-Sulfonylacrylates:  Stereoselective Synthesis of Sulfone-Substituted Cyclopropanes

  摘要：

  Reaction of 1-(phenylseleno)-2-(trimethylsilyl)ethene 1 and methyl or ethyl 2-p-toluene- or benzene-sulfonylacrylates 3 in the presence of SnCl4 at -78 degrees C gave sulfone-substituted cyclopropanes 4 as single stereoisomers. The structure of one of these crystalline cyclopropane products was elucidated by X-ray crystallographic analysis. The relative stereochemistry of the cyclopropane ring carbon (C-2) and selenosilylmethyl group was determined as R,R and S,S, which is consistent with previous mechanical considerations and the NOE determination. 2-Sulfinyl acrylate 2 did not undergo this cycloaddition. The difference in reactivity of the sulfoxide 2 and sulfones 3 toward 1 was explained by comparison of LUMO levels of 2-SnCl4 and 3-SnCl4 complexes and activation energies in the synclinal addition of 1 to the complexes.

  DOI：

  10.1021/jo9911591
• 作为产物：
  描述：

  sodium 4-methylbenzenesulfinate 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 2-(p-toluenesulfonyl)propanate
  参考文献：
  名称：

  Levkovskaya, G. G.; Guseva, S. A.; Kryukova, Yu. I., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 7, p. 1310 - 1314

  摘要：

  DOI：

文献信息

• Straightforward Access to Terminally Disubstituted Electron‐Deficient Alkylidene Cyclopent‐2‐en‐4‐ones through Olefination with α‐Carbonyl and α‐Cyano Secondary Alkyl Sulfones
  作者：Lena Trifonov、Ayelet Rothstein、Edward E. Korshin、Olga Viskind、Michal Afri、Gregory Leitus、Krzysztof Palczewski、Arie Gruzman

  DOI：10.1002/ejoc.202101258

  日期：2021.12.28

  A straightforward synthesis of virtually unexplored terminally disubstituted electron-deficient alkylidene cyclopent-2-en-4-ones was elaborated using activated secondary sulfones as alkylidene anion-radical synthons. The presented olefination process is proposed to rely on a base-promoted tandem or sequential Michael addition of C-nucleophiles to 4-acyl- or 4-silyloxycyclopent-2-en-1-ones followed

  使用活化的仲砜作为亚烷基阴离子自由基合成子，详细阐述了几乎未探索的末端双取代的缺电子亚烷基环戊二烯环戊二烯的直​​接合成。提出的烯化过程依赖于碱促进的串联或顺序迈克尔加成 C-亲核试剂到 4-酰基-或 4-甲硅烷氧基环戊-2-en-1-ones，然后是逆-迈克尔 O-和 S-核离心机消除。
• Preparation of SRN1-Type Coupling Adducts from Aliphatic gem-Dinitro Compounds in Ionic Liquids
  作者：Akio Kamimura、Seiichi Toyoshima

  DOI：10.3390/molecules17054782

  日期：——

  SRN1-type coupling adducts are readily prepared by the reaction between α-sulfonylesters or α-cyanosulfones and gem-dinitro compounds in ionic liquids. The reactions progress smoothly and recovered ionic liquids can be used for several iterations, as long as they are washed with water to remove alkali metallic salts. The reaction rate is slower than the corresponding SRN1 reaction in DMSO, but no acceleration

  SRN1 型偶联加合物很容易通过 α-磺酰酯或 α-氰基砜与双硝基化合物在离子液体中的反应制备。反应进展顺利，回收的离子液体只要用水洗涤除去碱金属盐，就可以反复使用。反应速率比 DMSO 中相应的 SRN1 反应慢，但在 m-DNB 存在下没有观察到辐照加速或抑制。
• Telomerization of butadiene and isoprene with sulfones containing active methine and methylene groups, catalyzed by palladium complexes
  作者：G. A. Tolstikov、O. A. Rozentsvet、R. V. Kunakova、N. N. Novitskaya

  DOI：10.1007/bf00953090

  日期：1983.3
• Telomerization of 2-cyclopropyl-1,3-butadiene with active methylene compounds
  作者：G. A. Tolstikov、O. A. Rozentsvet

  DOI：10.1007/bf00954367

  日期：1983.7
• LIU, GUANG-JIAN;ZHANG, ZHEN;SUN, YU-PING;WANG, YU-LIANG;CAI, SONG-CHUAN, YUTSZI XAUSYUEH, 10,(1990) N, S. 217-222
  作者：LIU, GUANG-JIAN、ZHANG, ZHEN、SUN, YU-PING、WANG, YU-LIANG、CAI, SONG-CHUAN

  DOI：——

  日期：——