Boc-1-(4-vinylphenyl)ethylamine | 147803-84-7

• 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: Boc-1-(4-vinylphenyl)ethylamine
• 英文别名: N-[1-(4-ethenylphenyl)ethyl]carbamic acid tert-butyl ester；tert-butyl N-[1-(4-ethenylphenyl)ethyl]carbamate
• CAS: 147803-84-7
• 化学式: C₁₅H₂₁NO₂
• 分子量: 247.337
• InChiKey: GVJYUIQFCRCQPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Boc-1-(4-vinylphenyl)ethylamine 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.5h， 以93%的产率得到R,S-1-(4-vinylphenyl)ethylamine hydrochloride
  参考文献：
  名称：

  Polymeric Pd catalysts for the reduction of acetamidocinnamic acid azlactone and its solvolysis products

  摘要：

  Pd complexes have been obtained from linear and cross-linked copolymers of R,S-,R-, and S-1-(4-vinylphenyl)ethyl-amine (1) with styrene and divinylbenzene. Reduction of these compounds gave catalysts which were active in the reductive solvolysis of alpha-acetaminocinnamic acid azlactone (2) and hydrogenation of the solvolysis products alpha-acetamidocinnamic acid (ACA), its esters, and its 1-phenylethylamide. The catalysts showed no enantioselective properties in the reductive hydrolysis, but were more active than the catalyst obtained in the absence of the polymer (the ''monomeric'' analog). The use of polymeric catalysts has shown that, in reductive aminolysis, the chiral nucleophile plays the dominant part in determining the stereoselectivity of the reaction, rather than the chiral ligand of the catalytic complex. The polymer matrix stabilizes the low-valent state of the palladium in the complex. In the hydrogenation of ACA and its esters, the catalyst on the cross-linked polymer is much more active than its ''monomeric'' analog, but showed no enantioselectivity. Hydrogenation of acetamidocinnamic acid R- and S-1-phenylethylamides on a chiral Pd-polymer catalyst occurred with double asymmetric induction.

  DOI：

  10.1007/bf00863823
• 作为产物：
  描述：

  Boc-1-(4-β-bromoethylphenyl)ethylamine 在 sodium ethanolate 作用下， 反应 0.5h， 以90%的产率得到Boc-1-(4-vinylphenyl)ethylamine
  参考文献：
  名称：

  Polymeric Pd catalysts for the reduction of acetamidocinnamic acid azlactone and its solvolysis products

  摘要：

  Pd complexes have been obtained from linear and cross-linked copolymers of R,S-,R-, and S-1-(4-vinylphenyl)ethyl-amine (1) with styrene and divinylbenzene. Reduction of these compounds gave catalysts which were active in the reductive solvolysis of alpha-acetaminocinnamic acid azlactone (2) and hydrogenation of the solvolysis products alpha-acetamidocinnamic acid (ACA), its esters, and its 1-phenylethylamide. The catalysts showed no enantioselective properties in the reductive hydrolysis, but were more active than the catalyst obtained in the absence of the polymer (the ''monomeric'' analog). The use of polymeric catalysts has shown that, in reductive aminolysis, the chiral nucleophile plays the dominant part in determining the stereoselectivity of the reaction, rather than the chiral ligand of the catalytic complex. The polymer matrix stabilizes the low-valent state of the palladium in the complex. In the hydrogenation of ACA and its esters, the catalyst on the cross-linked polymer is much more active than its ''monomeric'' analog, but showed no enantioselectivity. Hydrogenation of acetamidocinnamic acid R- and S-1-phenylethylamides on a chiral Pd-polymer catalyst occurred with double asymmetric induction.

  DOI：

  10.1007/bf00863823