(Z)-2-methoxy-1-(phenylsulfonyl)ethylene | 33823-30-2

• 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: (Z)-2-methoxy-1-(phenylsulfonyl)ethylene
• 英文别名: (Z)-2-methoxy-1-(phenylsulfonyl)ethene；cis-β-Methoxyvinylphenylsulfon；[(Z)-2-methoxyethenyl]sulfonylbenzene
• CAS: 33823-30-2
• 化学式: C₉H₁₀O₃S
• 分子量: 198.243
• InChiKey: DOROETGXWDWAGF-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (Z)-2-methoxy-1-(phenylsulfonyl)ethylene 在 正丁基锂 、 氘代甲醇-d 作用下， 生成 (E)-1-deuterio-2-methoxy-1-(phenylsulfonyl)ethylene
  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：

  甲醇 、 顺-1,2-双(苯基磺酰基)乙烯 在 sodium methylate 作用下， 以95%的产率得到(Z)-2-methoxy-1-(phenylsulfonyl)ethylene
  参考文献：
  名称：

  Alkylation of 2-oxy-substituted 1-sulfonylallyl and 1-sulfonylvinyl anions. New routes to functionalized carbocycles and dihydrofurans

  摘要：

  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.

  DOI：

  10.1021/jo00011a021

文献信息

• Chemical reactivity and configurational properties of cyclopropyl carbanions derived from a silyl sulfonyl substituted cyclopropene
  作者：Albert Padwa、M. Woods Wannamaker、Andrew D. Dyszlewski

  DOI：10.1021/jo00230a020

  日期：1987.10
• 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：——
• PADWA, ALBERT;WANNAMAKER, M. WOODS;DYSZLEWSKI, ANDREW D., J. ORG. CHEM., 52,(1987) N 21, 4760-4767
  作者：PADWA, ALBERT、WANNAMAKER, M. WOODS、DYSZLEWSKI, ANDREW D.

  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：——