arizonin C1 | 108890-86-4

• 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: arizonin C1
• 英文别名: (3aR,5R,11bR)-7,8-dimethoxy-5-methyl-3,3a,5,11b-tetrahydro-2H-benzo[g]furo[3,2-c]isochromene-2,6,11-trione；(3aR,5R,11bR)-3,3a,5,11b-tetrahydro-7,8-dimethoxy-5-methyl-1,4-dioxacyclopent[a]anthracen-2,6,11-trione；(11R,15R,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
• CAS: 108890-86-4
• 化学式: C₁₈H₁₆O₇
• 分子量: 344.321
• InChiKey: CSCPOKATULRWMV-ZEMFEACUSA-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

• 作为产物：
  描述：

  (4R,5R)-4-hydroxy-5-(1,4,5,6-tetramethoxynaphth-2-yl)dihydrofuran-2(3H)-one 在 ammonium cerium (IV) nitrate 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.25h， 生成 arizonin C1
  参考文献：
  名称：

  A concise total synthesis of arizonins B1 and C1

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2013.10.011

文献信息

• Controlling the Substitution Pattern of Hexasubstituted Naphthalenes by Aryne/Siloxyfuran Diels-Alder Additions: Regio- and Stereocontrolled Synthesis of Arizonin C1 Analogs
  作者：Markus Neumeyer、Julia Kopp、Reinhard Brückner

  DOI：10.1002/ejoc.201700195

  日期：2017.5.26

  3,4-Dimethoxybenz-1-yne and 2-siloxylated furans without or with a bromine atom at C-3 undergo Diels–Alder reactions with orientational selectivity. Hydrolysis furnished a bromine-free or a bromine-containing naphthalene, respectively. Bromination of the former provided a regioisomer of the latter. Either of the two compounds was processed to give a variety of unnatural naphthoquinonopyrano-γ-lactones

  在C-3处不带有或带有溴原子的3,4-二甲氧基苯-1-炔和2-甲氧基化的呋喃会发生定向选择性的Diels-Alder反应。水解分别提供了无溴或含溴的萘。前者的溴化提供了后者的区域异构体。两种化合物中的任何一种都经过处理后得到各种非天然的萘醌对吡喃酮-γ-内酯。这是由于一系列的（1）Heck偶联，（2）不对称的二羟基化，（3）oxa-Pictet-Spengler环化和（4）氧化而发生的。我们制备的15种单体萘醌-吡喃-γ-内酯结构类似于天然产物（-）-arizonin C1或C-5差向异构体。因此，它们同样代表六取代的萘。我们合成的第十六个萘醌对吡喃酮-γ-内酯是一种二聚体。
• First Synthesis of the Pyrano-Naphthoquinone Lactone (-)-Arizonin C1
  作者：Manuel Mahlau、Rodney A. Fernandes、Reinhard Brückner

  DOI：10.1002/ejoc.201100599

  日期：2011.6.21

  dihydroxylation of β,γ-unsaturated ester 9d as a highly enantioselective (>99 % ee) access to the γ-lactone intermediate 7d. Oxa-Pictet–Spengler cyclization, oxidation, and epimerization as expected led to the conversion of 7d into 2d. The pentasubstituted naphthalene precursor 14 of ester 9d was obtained by Dotz benzannulation.

  与γ-内酯环稠合的吡喃-萘醌是结构和生物学上有趣的天然产物。我们已经通过九个步骤完成了 (-)-arizonin C1 (2d) 的对映选择性合成。我们采用 Sharpless 二羟基化 β,γ-不饱和酯 9d 作为对 γ-内酯中间体 7d 的高度对映选择性 (>99% ee)。如预期的那样，Oxa-Pictet-Spengler 环化、氧化和差向异构化导致 7d 转化为 2d。酯9d的五取代萘前体14通过Dotz苯并环化获得。
• 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.