methyl 2-(N-benzylamino)-3-butenoate | 131489-56-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-(N-benzylamino)-3-butenoate
• 英文别名: methyl 2-(benzylamino)-3-butenoate；Methyl 2-(benzylamino)but-3-enoate
• CAS: 131489-56-0
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: BZNACPLMNZSALQ-UHFFFAOYSA-N

物化性质

• 沸点：
  299.8±28.0 °C(Predicted)
• 密度：
  1.046±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-<(tert-butyldimethylsilyl)oxy>-1-methoxy-1,3-butadiene 在 zinc(II) chloride 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 25.0h， 生成 methyl 2-(N-benzylamino)-3-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

• Nucleophilic Displacement Reactions of 4-(Nosyloxy)-2,3- unsaturated Esters and 2-(Nosyloxy)-3,4-unsaturated Esters
  作者：Robert V. Hoffman、Bryon S. Severns

  DOI：10.1021/jo960477m

  日期：1996.1.1

  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.
• 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：——