5-epi-arizonin C1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异色满醌
• 英文名称: 5-epi-arizonin C1
• 英文别名: 5-epi-arizonin B1；(11S,15S,17R)-4,5-dimethoxy-17-methyl-12,16-dioxatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3(8),4,6-tetraene-2,9,13-trione
• 化学式: C₁₈H₁₆O₇
• 分子量: 344.321
• InChiKey: CSCPOKATULRWMV-KCYKFYDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-epi-arizonin C1 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以56%的产率得到5-epi-arizonin C1
  参考文献：
  名称：

  Synthe1sis of 5-epi-arizonin B1 and 5-epi-arizonin C1

  摘要：

  The first synthesis of 5-epi-arizonin B1 (19) and 5-epi-arizonin C1 (18) is described in which the key step involves rearrangement of a furo[3,2-b]naphtho[2,1-d]furan (16) to a furo[3,2-b]naphtho[2,3-b]naphtho[2,3-d]pyran (17). Regioselective synthesis of naphthoquinone (15) was crucial to this synthetic strategy.

  DOI：

  10.1016/s0040-4039(00)73868-8
• 作为产物：
  描述：

  2,3-二甲氧基苯酚 在 盐酸 、 三乙基硅烷 、 4-二甲氨基吡啶 、 正丁基锂 、 ammonium cerium(IV) nitrate 、 salcomine 、 三氟化硼乙醚 、 溴 、 氧气 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 125.66h， 生成 5-epi-arizonin C1
  参考文献：
  名称：

  Brimble, Margaret A.; Phythian, Sara J.; Prabaharan, Hishani, Journal of the Chemical Society. Perkin transactions I, 1995, # 22, p. 2855 - 2860

  摘要：

  DOI：

文献信息

• Establishing Consensus Stereostructures for the Naphthoquinonopyrano-γ-lactone Natural Products (-)-Arizonin B1 and (-)-Arizonin C1 by Total Syntheses. Diastereocontrol of Oxa-Pictet-Spengler Cyclizations by Protective-Group Optimization
  作者：Markus Neumeyer、Reinhard Brückner

  DOI：10.1002/ejoc.201700013

  日期：2017.5.3

  Previous total syntheses of the naphthoquinonopyrano‐γ‐lactone arizonin C1 led to opposite assignments of its absolute configuration. Here we disclose another total synthesis thereof and the first total synthesis of arizonin B1 different than via arizonin C1. The correctness of Fernandes' configurational assignments of arizonin C1 and B1 was thereby ascertained.

  以前萘萘醌-γ-内酯arizonin C1的全部合成导致了其绝对构型的相反分配。在这里，我们公开了其另一种全合成方法以及与通过arizonin C1不同的arizonin B1的第一种全合成方法。从而确定了费尔南德斯（Arizonin）C1和B1的构型分配的正确性。
• A concise total synthesis of arizonins B1 and C1
  作者：Rodney A. Fernandes、Sandip V. Mulay、Vijay P. Chavan

  DOI：10.1016/j.tetasy.2013.10.011

  日期：2013.12

  A concise and efficient total synthesis of arizonins B1 and C1 is reported. A key building block alkyne is synthesized from a-glucono-S-lactone and used in the Dotz benzannulation reaction to construct the naphthalene unit. An oxa-Pictet-Spengler reaction gave the pyran ring while an H2SO4 mediated isomerization set the correct stereochemistry of the target molecules. Alternatively, a direct anti-pyran stereochemistry was prepared in a TFA solvent. The synthesis is competitive to previous reports and marks the first enantioselective synthesis of arizonin B1. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthe1sis of 5-epi-arizonin B1 and 5-epi-arizonin C1
  作者：Margaret A. Brimble、Sara J. Phythian

  DOI：10.1016/s0040-4039(00)73868-8

  日期：1993.9

  The first synthesis of 5-epi-arizonin B1 (19) and 5-epi-arizonin C1 (18) is described in which the key step involves rearrangement of a furo[3,2-b]naphtho[2,1-d]furan (16) to a furo[3,2-b]naphtho[2,3-b]naphtho[2,3-d]pyran (17). Regioselective synthesis of naphthoquinone (15) was crucial to this synthetic strategy.
• Brimble, Margaret A.; Phythian, Sara J.; Prabaharan, Hishani, Journal of the Chemical Society. Perkin transactions I, 1995, # 22, p. 2855 - 2860
  作者：Brimble, Margaret A.、Phythian, Sara J.、Prabaharan, Hishani

  DOI：——

  日期：——