(3R,4R)-4-[(6-bromo-1,3-benzodioxol-5-yl)methyl]-3-[(3,4,5-trimethoxyphenyl)amino]dihydrofuran-2(3H)-one | 1448019-82-6

• 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: (3R,4R)-4-[(6-bromo-1,3-benzodioxol-5-yl)methyl]-3-[(3,4,5-trimethoxyphenyl)amino]dihydrofuran-2(3H)-one
• 英文别名: (3R,4R)-4-[(6-bromo-1,3-benzodioxol-5-yl)methyl]-3-(3,4,5-trimethoxyanilino)oxolan-2-one
• CAS: 1448019-82-6
• 化学式: C₂₁H₂₂BrNO₇
• 分子量: 480.312
• InChiKey: VKKXYBCOSJPHCM-HXPMCKFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3R,4R)-4-[(6-bromo-1,3-benzodioxol-5-yl)methyl]-3-[(3,4,5-trimethoxyphenyl)amino]dihydrofuran-2(3H)-one 在 2-双环己基膦-2',6'-二甲氧基联苯 、 tris-(dibenzylideneacetone)dipalladium(0) 、 caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以51%的产率得到(5aS,8aR)-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydro-1,3-dioxolo[4,5-g]furo[3,4-b]quinolin-6(5aH)-one
  参考文献：
  名称：

  Asymmetric Synthesis of 1-Aza-4-deoxypicropodophyllotoxin

  摘要：

  In our search for new easily accessible analogues based on the natural product podophyllotoxin, we synthesized 1-aza-4-deoxypicropodophyllotoxin in good overall yield and excellent enantioselectivity. The synthesis was centered around a direct asymmetric Mannich reaction using D-proline as the key step for introduction of the chiral centres. Our synthesis of 1-aza-4-deoxypodophyllotoxin was hindered through the increased instability towards epimerization of the C2 position. We did, however, synthesized a new scaffold based on the opened lactone analogue.

  DOI：

  10.1055/s-0033-1338414
• 作为产物：
  描述：

  3,4-methylenedioxy-trans-cinnamic acid 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 草酰氯 、 硫酸 、 palladium 10% on activated carbon 、 氢气 、 溴 、 二甲基亚砜 、 D-脯氨酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， -78.0~20.0 ℃ 、379.22 kPa 条件下， 反应 45.75h， 生成 (3R,4R)-4-[(6-bromo-1,3-benzodioxol-5-yl)methyl]-3-[(3,4,5-trimethoxyphenyl)amino]dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Asymmetric Synthesis of 1-Aza-4-deoxypicropodophyllotoxin

  摘要：

  In our search for new easily accessible analogues based on the natural product podophyllotoxin, we synthesized 1-aza-4-deoxypicropodophyllotoxin in good overall yield and excellent enantioselectivity. The synthesis was centered around a direct asymmetric Mannich reaction using D-proline as the key step for introduction of the chiral centres. Our synthesis of 1-aza-4-deoxypodophyllotoxin was hindered through the increased instability towards epimerization of the C2 position. We did, however, synthesized a new scaffold based on the opened lactone analogue.

  DOI：

  10.1055/s-0033-1338414

文献信息

• Asymmetric Synthesis of 1-Aza-4-deoxypicropodophyllotoxin
  作者：Wim De Borggraeve、Benoit Aigret、Jeroen Jacobs、Luc Van Meervelt

  DOI：10.1055/s-0033-1338414

  日期：——

  In our search for new easily accessible analogues based on the natural product podophyllotoxin, we synthesized 1-aza-4-deoxypicropodophyllotoxin in good overall yield and excellent enantioselectivity. The synthesis was centered around a direct asymmetric Mannich reaction using D-proline as the key step for introduction of the chiral centres. Our synthesis of 1-aza-4-deoxypodophyllotoxin was hindered through the increased instability towards epimerization of the C2 position. We did, however, synthesized a new scaffold based on the opened lactone analogue.