dimethyl 2-[2-(tert-butoxycarbonylamino)-4-methylphenyl]malonate | 1257322-05-6

• 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: dimethyl 2-[2-(tert-butoxycarbonylamino)-4-methylphenyl]malonate
• 英文别名: Dimethyl 2-[4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]propanedioate；dimethyl 2-[4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]propanedioate
• CAS: 1257322-05-6
• 化学式: C₁₇H₂₃NO₆
• 分子量: 337.373
• InChiKey: OGNIGUPLYPBKNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  cis-1,4-二乙酰氧基-2-丁烯 、 dimethyl 2-[2-(tert-butoxycarbonylamino)-4-methylphenyl]malonate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 BINAP 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以71%的产率得到1-tert-butyl 4,4-dimethyl 7-methyl-2-vinyl-2,3-dihydroquinoline-1,4,4-tricarboxylate
  参考文献：
  名称：

  Highly regioselective synthesis of substituted tetrahydroquinolines by palladium-catalyzed cyclization of substituted 2-amidophenylmalonates with 1,4-diacetoxybut-2-ene

  摘要：

  The reaction of 2-amidophenylmalonates with 1,4-diacetoxybut-2-ene in the presence of a palladium catalyst is described. Substituted tetrahydroquinolines having a vinyl group at the 3- or 2-position were synthesized, in which the regioselectivities of the double allylic substitution reactions have been altered depending on the substituent on the amino group. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.09.033
• 作为产物：
  描述：

  dimethyl 2-(4-methyl-2-nitrophenyl)malonate 在 10% Pd/C 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 20.0 ℃ 、354.66 kPa 条件下， 反应 2.0h， 生成 dimethyl 2-[2-(tert-butoxycarbonylamino)-4-methylphenyl]malonate
  参考文献：
  名称：

  Regio- and enantioselective synthesis of functionalized tetrahydroquinolines by palladium-catalyzed cyclization of 2-amidophenylmalonates with allylic bisacetates

  摘要：

  A palladium-catalyzed cyclization of 2-amidophenylmalonates with allylic bisacetates is described. Tetrahydroquinolines having a vinyl group at the 3- or 2-position were produced, in which the regioselectivity of the resulting products was altered depending on the substituent on the amino group. The product was transformed to the azabicyclo[3.3.1]nonene via the ring-closing metathesis. Enantioselective reactions also successfully proceeded in the presence of (S)-BINAP to give the optically active tetrahydroquinoline with high enantioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.075

文献信息

• Highly regioselective synthesis of substituted tetrahydroquinolines by palladium-catalyzed cyclization of substituted 2-amidophenylmalonates with 1,4-diacetoxybut-2-ene
  作者：Masahiro Yoshida、Yohei Maeyama、Kozo Shishido

  DOI：10.1016/j.tetlet.2010.09.033

  日期：2010.11

  The reaction of 2-amidophenylmalonates with 1,4-diacetoxybut-2-ene in the presence of a palladium catalyst is described. Substituted tetrahydroquinolines having a vinyl group at the 3- or 2-position were synthesized, in which the regioselectivities of the double allylic substitution reactions have been altered depending on the substituent on the amino group. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.
• Regio- and enantioselective synthesis of functionalized tetrahydroquinolines by palladium-catalyzed cyclization of 2-amidophenylmalonates with allylic bisacetates
  作者：Masahiro Yoshida、Yohei Maeyama、Kozo Shishido

  DOI：10.1016/j.tet.2012.09.075

  日期：2012.12

  A palladium-catalyzed cyclization of 2-amidophenylmalonates with allylic bisacetates is described. Tetrahydroquinolines having a vinyl group at the 3- or 2-position were produced, in which the regioselectivity of the resulting products was altered depending on the substituent on the amino group. The product was transformed to the azabicyclo[3.3.1]nonene via the ring-closing metathesis. Enantioselective reactions also successfully proceeded in the presence of (S)-BINAP to give the optically active tetrahydroquinoline with high enantioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.