2-methallyloxy-[1,4]naphthoquinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-methallyloxy-[1,4]naphthoquinone
• 英文别名: 2-Methallyloxy-[1,4]naphthochinon；2-Methylallyloxy-1,4-naphthoquinone；2-(2-Methylprop-2-enoxy)naphthalene-1,4-dione
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: BCQQBPDPWQONGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methallyloxy-[1,4]naphthoquinone 在 五氯化铌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以88%的产率得到2,2-dimethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione
  参考文献：
  名称：

  NbCl 5介导的仿生级联反应：邓尼酮和正β-拉帕酮的高效且可扩展的一锅合成

  摘要：

  描述了生物活性天然产物地尼酮和去甲β-拉帕酮的区域选择性仿生合成。这种级联反应提供了由路易斯酸NbCl 5介导的一锅过程的新策略，该过程涉及串联的克莱森重排-环化反应。该过程高效，温和且易于扩展，避免了使用高危险浓度的H 2 SO 4的情况。

  DOI：

  10.1016/j.tetlet.2014.11.107
• 作为产物：
  描述：

  2-羟基-1,4-萘醌 、 3-溴-2-甲基丙烯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 2-methallyloxy-[1,4]naphthoquinone
  参考文献：
  名称：

  Synthesis and evaluation of (±)-dunnione and its ortho-quinone analogues as substrates for NAD(P)H:quinone oxidoreductase 1 (NQO1)

  摘要：

  Natural product (+/-)-dunnione (2) and its ortho-quinone analogues (3-8) were synthesized and found to be substrates for NQO1. The structure-activity relationship study revealed that the biological activity was favored by the presence of methyl group at the C ring and methoxy group at the A ring. The docking studies supported the rationalization of the metabolic studies. Deeper location in the active site of NQO1, interactions with hydrophobic pocket and C-H center dot center dot center dot pi interactions with the adjacent Phe178 residue contributed to the better catalytic efficiency and specificity to NQO1. Cytotoxicity studies and determination of superoxide (O-2(center dot)) production in the presence and absence of the NOQ1 inhibitor dicoumarol confirmed that the ortho-quinones exerted their antitumor activity through NQO1-mediated ROS production by redox cycling. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.01.057

文献信息

• NbCl5 mediated biomimetic cascade reaction: efficient and scalable one-pot synthesis of dunnione and nor-β-lapachone
  作者：Jinlei Bian、Xue Qian、Jun Fan、Xiang Li、Haopeng Sun、Qidong You、Xiaojin Zhang

  DOI：10.1016/j.tetlet.2014.11.107

  日期：2015.1

  A regioselective biomimetic synthesis of bioactive natural products dunnione and nor-β-lapachone is described. This cascade provides a new strategy of a one-pot process mediated by Lewis acid NbCl5 involving a tandem Claisen rearrangement–cyclization reaction. This procedure was efficient, mild, and easily scalable that avoided using highly hazardous concd H2SO4.

  描述了生物活性天然产物地尼酮和去甲β-拉帕酮的区域选择性仿生合成。这种级联反应提供了由路易斯酸NbCl 5介导的一锅过程的新策略，该过程涉及串联的克莱森重排-环化反应。该过程高效，温和且易于扩展，避免了使用高危险浓度的H 2 SO 4的情况。
• Cooke; Somers, Australian Journal of Scientific Research, Series A: Physical Sciences, 1950, vol. 3, p. 466,474
  作者：Cooke、Somers

  DOI：——

  日期：——
• Synthesis and evaluation of (±)-dunnione and its ortho-quinone analogues as substrates for NAD(P)H:quinone oxidoreductase 1 (NQO1)
  作者：Jinlei Bian、Lili Xu、Bang Deng、Xue Qian、Jun Fan、Xiuwen Yang、Fang Liu、Xiaoli Xu、Xiaoke Guo、Xiang Li、Haopeng Sun、Qidong You、Xiaojin Zhang

  DOI：10.1016/j.bmcl.2015.01.057

  日期：2015.3

  Natural product (+/-)-dunnione (2) and its ortho-quinone analogues (3-8) were synthesized and found to be substrates for NQO1. The structure-activity relationship study revealed that the biological activity was favored by the presence of methyl group at the C ring and methoxy group at the A ring. The docking studies supported the rationalization of the metabolic studies. Deeper location in the active site of NQO1, interactions with hydrophobic pocket and C-H center dot center dot center dot pi interactions with the adjacent Phe178 residue contributed to the better catalytic efficiency and specificity to NQO1. Cytotoxicity studies and determination of superoxide (O-2(center dot)) production in the presence and absence of the NOQ1 inhibitor dicoumarol confirmed that the ortho-quinones exerted their antitumor activity through NQO1-mediated ROS production by redox cycling. (C) 2015 Elsevier Ltd. All rights reserved.
• NOVEL ORTHO-NAPHTHOQUINONE DERIVATIVES, NOVEL SYNTHESIS THEREFOR, AND THEIR USE IN THE INHIBITION OF NEOPLASTIC CELL GROWTH
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：EP0888326A2

  公开（公告）日：1999-01-07
• US5824700A
  申请人：——

  公开号：US5824700A

  公开（公告）日：1998-10-20