(Z)-methyl-3-bromo-2-(bis(tert-butoxycarbonyl)amino)acrylate | 1418736-02-3

• 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: (Z)-methyl-3-bromo-2-(bis(tert-butoxycarbonyl)amino)acrylate
• CAS: 1418736-02-3
• 化学式: C₁₄H₂₂BrNO₆
• 分子量: 380.236
• InChiKey: ICVPNKGSTOOELV-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  82.14
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-((R)-2,8-dimethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 、 (Z)-methyl-3-bromo-2-(bis(tert-butoxycarbonyl)amino)acrylate 在 potassium phosphate 、 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以85%的产率得到(Z)-methyl 2-((tert-butoxycarbonyl)amino)-3-((R)-2,8-dimethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-yl)acrylate
  参考文献：
  名称：

  Facile conversion of chromane-6-triflate to chromane-6-alanines under palladium conditions

  摘要：

  Conversion of chromane-6-triflate 5 to chromane-6-dehydroalanine 9 or 10 via its Bpin-derivative 6 followed by Suzuki coupling with protected dehydroalanine bromides 7 or 8 were reported (86%). Alternatively, a palladium-catalyzed stannation of 5 with Bu6Sn2 afforded the tributyltin derivative 11, and iodination (12) followed by coupling with 13 gave chromane-6-alanine 15 (75%). Either approach constitutes a conversion from chromane-6-triflate to the corresponding protected chromane-6-alanine or its dehydro analog. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.115
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 (Z)-3-bromo-2-[[(1,1-dimethylethyloxy)carbonyl]amino]-2-propenoic acid methyl ester 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以83%的产率得到(Z)-methyl-3-bromo-2-(bis(tert-butoxycarbonyl)amino)acrylate
  参考文献：
  名称：

  Facile conversion of chromane-6-triflate to chromane-6-alanines under palladium conditions

  摘要：

  Conversion of chromane-6-triflate 5 to chromane-6-dehydroalanine 9 or 10 via its Bpin-derivative 6 followed by Suzuki coupling with protected dehydroalanine bromides 7 or 8 were reported (86%). Alternatively, a palladium-catalyzed stannation of 5 with Bu6Sn2 afforded the tributyltin derivative 11, and iodination (12) followed by coupling with 13 gave chromane-6-alanine 15 (75%). Either approach constitutes a conversion from chromane-6-triflate to the corresponding protected chromane-6-alanine or its dehydro analog. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.115