(+)-tert-butyl (R)-3-(N-chloro-N-(mesitylmethyl)amino)-3-phenylpropanoate | 909786-10-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+)-tert-butyl (R)-3-(N-chloro-N-(mesitylmethyl)amino)-3-phenylpropanoate
• 英文别名: tert-butyl (3R)-3-[chloro-[(2,4,6-trimethylphenyl)methyl]amino]-3-phenylpropanoate
• CAS: 909786-10-3
• 化学式: C₂₃H₃₀ClNO₂
• 分子量: 387.95
• InChiKey: HAOKGGCKVXNJDP-OAQYLSRUSA-N

物化性质

• 沸点：
  493.4±55.0 °C(Predicted)
• 密度：
  1.096±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-tert-butyl (R)-3-(N-chloro-N-(mesitylmethyl)amino)-3-phenylpropanoate 在 盐酸羟胺 、 四甲基胍 作用下， 以 四氢呋喃 、 水 、 苯 为溶剂， 反应 17.25h， 生成 (3R)-3-氨基-3-苯基丙酸叔丁酯
  参考文献：
  名称：

  Chiral ligand-controlled asymmetric conjugate amination of enoates with lithium mesitylmethyl(trimethylsilyl)amide

  摘要：

  Lithium mesitylmethyl(trimethylsilyl)amide behaved as a nice amination agent in a chiral ligand-controlled conjugate addition reaction of tert-butyl cinnamate to give the conjugate amination product with 99% ee in 90% yield. Other acyclic and cyclic enoates were also aminated in reasonably high enantioselectivity, while the deprotonation of abstractable proton of enoates caused yield loss of the conjugate amination products, due to the bulkiness and enriched basicity of the lithium amide. Although such steric bulkiness made hard the hydrogenolytic cleavage of a mesitylmethyl-N bond of the adducts, a new protocol comprising N-chlorination-regioselective dehydro-chlorination-transoximation was developed for N-dearylmethylation, giving 3-aminoalkanoates in reasonably good yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.040
• 作为产物：
  描述：

  2,4,6-三甲基苄胺 在 N-氯代丁二酰亚胺 、 正丁基锂 、 (1R,2R)-1,2-dimethoxy-1,2-diphenylethane 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 16.5h， 生成 (+)-tert-butyl (R)-3-(N-chloro-N-(mesitylmethyl)amino)-3-phenylpropanoate
  参考文献：
  名称：

  Chiral ligand-controlled asymmetric conjugate amination of enoates with lithium mesitylmethyl(trimethylsilyl)amide

  摘要：

  Lithium mesitylmethyl(trimethylsilyl)amide behaved as a nice amination agent in a chiral ligand-controlled conjugate addition reaction of tert-butyl cinnamate to give the conjugate amination product with 99% ee in 90% yield. Other acyclic and cyclic enoates were also aminated in reasonably high enantioselectivity, while the deprotonation of abstractable proton of enoates caused yield loss of the conjugate amination products, due to the bulkiness and enriched basicity of the lithium amide. Although such steric bulkiness made hard the hydrogenolytic cleavage of a mesitylmethyl-N bond of the adducts, a new protocol comprising N-chlorination-regioselective dehydro-chlorination-transoximation was developed for N-dearylmethylation, giving 3-aminoalkanoates in reasonably good yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.040

文献信息

• Chiral ligand-controlled asymmetric conjugate amination of enoates with lithium mesitylmethyl(trimethylsilyl)amide
  作者：Takeo Sakai、Hirohisa Doi、Kiyoshi Tomioka

  DOI：10.1016/j.tet.2006.06.040

  日期：2006.8

  Lithium mesitylmethyl(trimethylsilyl)amide behaved as a nice amination agent in a chiral ligand-controlled conjugate addition reaction of tert-butyl cinnamate to give the conjugate amination product with 99% ee in 90% yield. Other acyclic and cyclic enoates were also aminated in reasonably high enantioselectivity, while the deprotonation of abstractable proton of enoates caused yield loss of the conjugate amination products, due to the bulkiness and enriched basicity of the lithium amide. Although such steric bulkiness made hard the hydrogenolytic cleavage of a mesitylmethyl-N bond of the adducts, a new protocol comprising N-chlorination-regioselective dehydro-chlorination-transoximation was developed for N-dearylmethylation, giving 3-aminoalkanoates in reasonably good yields. (c) 2006 Elsevier Ltd. All rights reserved.