methyl 1-(3,4-dioxo-3,4-dihydronaphthalen-1-yl)-2-oxocyclopentane-1-carboxylate | 1245654-34-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 1-(3,4-dioxo-3,4-dihydronaphthalen-1-yl)-2-oxocyclopentane-1-carboxylate
• CAS: 1245654-34-5
• 化学式: C₁₇H₁₄O₅
• 分子量: 298.295
• InChiKey: RRBAPYXMLBSCIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.75
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  77.51
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 1-(3,4-dioxo-3,4-dihydronaphthalen-1-yl)-2-oxocyclopentane-1-carboxylate 在 sodium dithionite 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以99%的产率得到methyl 1-(3,4-dihydroxynaphthalen-1-yl)-2-oxocyclopentane-1-carboxylate
  参考文献：
  名称：

  An oxidative coupling for the synthesis of arylated quaternary stereocentres and its application in the total synthesis of powelline and buphanidrine

  摘要：

  Catechol derivatives directly bonded to all-carbon quaternary stereocentres are prevalent in nature. An oxidative coupling strategy for the synthesis of this motif is described. Pivoting on the base-catalysed Michael addition of carbon-centred pro-nucleophiles to in situ generated ortho-benzoquinones, the method is broad in scope, high yielding and provides remarkably simple access to this challenging motif. The application of this methodology in the total synthesis of the crinane-type amaryllidaceae alkaloids (+/-)-powelline and (+/-)-buphanidrine is demonstrated and our efforts towards an enantioselective synthesis described. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.132
• 作为产物：
  描述：

  2-甲氧羰基环戊酮 、 1,2-萘醌 在 2-叔丁基亚氨基-2-二乙基氨基-1,3-二甲基全氢-1,3,2-二氮杂磷 作用下， 以 二氯甲烷 为溶剂， 反应 1.17h， 以42%的产率得到methyl 1-(3,4-dioxo-3,4-dihydronaphthalen-1-yl)-2-oxocyclopentane-1-carboxylate
  参考文献：
  名称：

  An oxidative coupling for the synthesis of arylated quaternary stereocentres and its application in the total synthesis of powelline and buphanidrine

  摘要：

  Catechol derivatives directly bonded to all-carbon quaternary stereocentres are prevalent in nature. An oxidative coupling strategy for the synthesis of this motif is described. Pivoting on the base-catalysed Michael addition of carbon-centred pro-nucleophiles to in situ generated ortho-benzoquinones, the method is broad in scope, high yielding and provides remarkably simple access to this challenging motif. The application of this methodology in the total synthesis of the crinane-type amaryllidaceae alkaloids (+/-)-powelline and (+/-)-buphanidrine is demonstrated and our efforts towards an enantioselective synthesis described. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.132