ethyl 4-<<(p-nitrophenyl)sulfonyl>oxy>-2-butenoate | 131489-50-4

• 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: ethyl 4-<<(p-nitrophenyl)sulfonyl>oxy>-2-butenoate
• 英文别名: ethyl (E)-4-(4-nitrophenyl)sulfonyloxybut-2-enoate
• CAS: 131489-50-4
• 化学式: C₁₂H₁₃NO₇S
• 分子量: 315.304
• InChiKey: PFUTUHDNBASPMU-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 4-<<(p-nitrophenyl)sulfonyl>oxy>-2-butenoate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以55%的产率得到ethyl (E)-4-azidobut-2-enoate
  参考文献：
  名称：

  Nucleophilic Displacement Reactions of 4-(Nosyloxy)-2,3- unsaturated Esters and 2-(Nosyloxy)-3,4-unsaturated Esters

  摘要：

  It has been found that 4-(nosyloxy)-2,3-unsaturated esters 2 undergo direct displacement with a wide variety of nucleophiles and yield 4-substituted-2,3-unsaturated products cleanly and in generally good yields. These materials thus have very good synthetic potential for the formation of densely functionalized unsaturated esters. 2-(Nosyloxy)-3,4-unsaturated esters as exemplified by methyl 2-(nosyloxy)-3-butenoate (3d) also undergo direct displacement with a range of good nucleophiles; however, the resulting substitution products are prone to rearrangements and tautomerism, as is the starting material itself, so that the synthetic utility of these compounds is limited.

  DOI：

  10.1021/jo960477m
• 作为产物：
  描述：

  ethyl 2-<<(p-nitrophenyl)sulfonyl>oxy>-3-butenoate 以 甲苯 为溶剂， 反应 24.0h， 以100%的产率得到ethyl 4-<<(p-nitrophenyl)sulfonyl>oxy>-2-butenoate
  参考文献：
  名称：

  Regiochemical control in the preparation of 2-(nosyloxy) .beta.,.gamma.-unsaturated esters and 4-(nosyloxy) .alpha.,.beta.-unsaturated esters from 1-[(trimethylsilyl)oxy]-1-alkoxy 1,3-dienes

  摘要：

  A series of 1-[(trialkylsilyl)oxy]-1-alkoxy 1,3-dienes 1a-i were found to react with p-nitrobenzenesulfonyl peroxide in the presence of sodium methoxide or zinc chloride to give alkyl 2-[[(p-nitrophenyl)sulfonyl]oxy] beta-gamma-unsaturated esters 3 and alkyl 4-[[(p-nitrophenyl)sulfonyl]oxy] alpha,beta-unsaturated esters 4 which are readily separable. The regioselectivity is determined by kinetic versus thermodynamic control. When positions 2 or 4 of the diene are unsubstituted, the 2-isomer is the major product and is the kinetically fastest formed product. It can be thermally rearranged to the more stable 4-isomer. When alkyl substituents are present at either the 2- or 4-positions, only the 4-isomer is obtained. Substitution for nosylate by amine nucleophiles occurs by an S(N)2 process. Thus 2-amino beta,gamma-unsaturated esters and 4-amino alpha,beta-unsaturated esters can be prepared from the appropriate starting nosylate.

  DOI：

  10.1021/jo00003a022

文献信息

• HOFFMAN, ROBERT V.;KIM, HWA-OK, J. ORG. CHEM., 56,(1991) N, C. 1014-1019
  作者：HOFFMAN, ROBERT V.、KIM, HWA-OK

  DOI：——

  日期：——