(E)-2-ethoxy-1-(p-tolylsulfonyl)ethylene | 54321-08-3

• 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: (E)-2-ethoxy-1-(p-tolylsulfonyl)ethylene
• 英文别名: (E)-1-[(2-ethoxyvinyl)sulfonyl]-4-methylbenzene；1-[(E)-2-ethoxyethenyl]sulfonyl-4-methylbenzene
• CAS: 54321-08-3
• 化学式: C₁₁H₁₄O₃S
• 分子量: 226.296
• InChiKey: GRFALNNPOLVOIA-CMDGGOBGSA-N

物化性质

• 熔点：
  57-58 °C
• 沸点：
  371.3±42.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 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：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-ethoxy-1-(p-tolylsulfonyl)ethylene 在 正丁基锂 、 重水 作用下， 以90%的产率得到1-[(E)-1-deuterio-2-ethoxyethenyl]sulfonyl-4-methylbenzene
  参考文献：
  名称：

  Configurational properties and chemical reactivity of mono and dianions derived from aryl 2-alkoxyvinyl sulfones

  摘要：

  DOI：

  10.1016/s0040-4039(00)95557-6
• 作为产物：
  描述：

  1-(2-ethoxy-2-phenylseleninylethyl)sulfonyl-4-methylbenzene 在 异丙胺 作用下， 以80%的产率得到(E)-2-ethoxy-1-(p-tolylsulfonyl)ethylene
  参考文献：
  名称：

  Ru(bpy)32+-mediated addition of Se-phenyl p-tolueneselenosulfonate to electron rich olefins

  摘要：

  The addition of Se-phenyl p-tolueneselenosulfonate 1 to electron rich olefins 4a-4e upon visible light photolysis with a catalytic amount of tris(2,2'-bipyridine)ruthenium(II) gives adducts 5 in high yield.

  DOI：

  10.1016/s0040-4039(00)76646-9

文献信息

• Synthesis of Vinyl Sulfoxides Using Sulfinyl Chlorides and Olefins
  作者：Xiancai Ding、Jianming Wen、Jianqiang Wang、Jun Yu、Jing-Hua Li

  DOI：10.3184/174751915x14304098020793

  日期：2015.5

  synthesis of vinyl sulfoxides, using sulfinyl chlorides and olefins as starting materials and DBU as an HCl scavenger, has been developed. Vinyl sulfoxides were obtained from the ZnCl2 catalysed addition of sulfinyl chlorides to olefins followed by the elimination with DBU. However, the direct reaction of sulfinyl chlorides with olefins in the presence of DBU, usually leads to generation of vinyl sulfones

  已经开发了一种合成乙烯基亚砜的通用方法，使用亚磺酰氯和烯烃作为起始原料，DBU 作为 HCl 清除剂。乙烯基亚砜是通过 ZnCl2 催化将亚磺酰氯加成到烯烃中，然后用 DBU 消除而获得的。然而，在 DBU 存在下，亚磺酰氯与烯烃的直接反应通常会导致生成乙烯基砜。由 DBU 介导的亚磺酰基歧化产生的磺酰基自由基与烯烃发生加成消除反应，得到乙烯基砜。
• Alkylation of 2-oxy-substituted 1-sulfonylallyl and 1-sulfonylvinyl anions. New routes to functionalized carbocycles and dihydrofurans
  作者：Albert Padwa、William H. Bullock、Andrew D. Dyszlewski、S. W. McCombie、B. B. Shankar、A. K. Ganguly

  DOI：10.1021/jo00011a021

  日期：1991.5

  Alkylation of the anion derived from 2-phenoxy-3-(phenylsulfonyl)-1-propene proceeds alpha to the phenylsulfonyl group and affords cyclic products from 1,omega-dihalides. Reaction of the monoalkylated products, in which a suitably positioned olefinic or acetylenic unit is present, with sodium benzenesulfinate-acetic acid gives functionalized acetylcyclopentenes and cyclohexenes via C-C bond formation from the allyl cation-sulfinate ion pair. In the vinyl sulfone series, deprotonation of (E)- or (Z)-2-alkoxyvinyl phenyl sulfones rapidly affords the more stable (E)-lithio derivative, an acetaldehyde anion equivalent which reacts normally with aldehydes, ketones, alkyl halides, and epoxides. The latter process may be effected in an intramolecular fashion. Thus, (E)-(2-phenylsulfonyl) vinyl ethers of 2,3-epoxy alcohols cyclize on treatment with amide bases to afford dihydrofurans whose stereochemistry is fully defined by that of the starting epoxy alcohol.
• PADWA, ALBERT;BULLOCK, WILLIAM H.;DYSZLEWSKI, ANDREW D.;MCCOMBIE, S. W.;S+, J. ORG. CHEM., 56,(1991) N1, C. 3556-3564
  作者：PADWA, ALBERT、BULLOCK, WILLIAM H.、DYSZLEWSKI, ANDREW D.、MCCOMBIE, S. W.、S+

  DOI：——

  日期：——
• Barton Derek H. R., Csiba Maria A., Jaszberenyi Joseph Cs., Tetrahedron Lett, 35 (1994) N 8, S 2869-2872
  作者：Barton Derek H. R., Csiba Maria A., Jaszberenyi Joseph Cs.

  DOI：——

  日期：——
• MCCOMBIE, S. W.;SHANKAR, B. B.;GANGULY, A. K.;PADWA, A.;BULLOCK, W. H.;DY+, TETRAHEDRON LETT., 28,(1987) N 36, 4127-4130
  作者：MCCOMBIE, S. W.、SHANKAR, B. B.、GANGULY, A. K.、PADWA, A.、BULLOCK, W. H.、DY+

  DOI：——

  日期：——