5-(methoxymethoxy)-1,4-naphthoquinone | 176040-42-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(methoxymethoxy)-1,4-naphthoquinone
• 英文别名: 5-(Methoxymethoxy)naphthalene-1,4-dione
• CAS: 176040-42-9
• 化学式: C₁₂H₁₀O₄
• 分子量: 218.209
• InChiKey: WAANNKVHBBWVMF-UHFFFAOYSA-N

物化性质

• 沸点：
  401.9±45.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(methoxymethoxy)-1,4-naphthoquinone 在 哌啶 、 吡啶 、 potassium carbonate 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 、 丙酮 、 乙腈 、 苯 为溶剂， 反应 71.33h， 生成 Methyl 10,12-dimethoxy-1-(methoxymethoxy)-6-oxonaphtho[1,2-c]isochromene-8-carboxylate
  参考文献：
  名称：

  An Inverse Electron Demand Diels–Alder-Based Total Synthesis of Defucogilvocarcin V and Some C-8 Analogues

  摘要：

  A concise total synthesis of defucogilvocarcin V is reported. The key features of the approach are the formation of the C-ring using a vinylogous Knoevenagel/transesterification reaction and construction of the D-ring by way of an inverse electron demand Diels-Alder-driven domino reaction. The resulting C-8 ester functionality provides a handle for the synthesis of defucogilvocarcin V as well as some C-8 analogues from a common late-stage intermediate.

  DOI：

  10.1021/jo3012682
• 作为产物：
  描述：

  1,5-二羟基萘 在 氧气 、 N,N-二异丙基乙胺 、 copper(l) chloride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 16.25h， 生成 5-(methoxymethoxy)-1,4-naphthoquinone
  参考文献：
  名称：

  An Inverse Electron Demand Diels–Alder-Based Total Synthesis of Defucogilvocarcin V and Some C-8 Analogues

  摘要：

  A concise total synthesis of defucogilvocarcin V is reported. The key features of the approach are the formation of the C-ring using a vinylogous Knoevenagel/transesterification reaction and construction of the D-ring by way of an inverse electron demand Diels-Alder-driven domino reaction. The resulting C-8 ester functionality provides a handle for the synthesis of defucogilvocarcin V as well as some C-8 analogues from a common late-stage intermediate.

  DOI：

  10.1021/jo3012682

文献信息

• Solar photochemistry: optimisation of the photo Friedel–Crafts acylation of naphthoquinones
  作者：Lorna J. Mitchell、William Lewis、Christopher J. Moody

  DOI：10.1039/c3gc41477a

  日期：——

  A practical and robust photo Friedel–Crafts acylation of naphthoquinones is described. Although the reaction proceeds slowly in sunlight, the optimised conditions offer a substantial improvement to those already reported, by the utilisation of a more reliable and practical ‘sun-mimicking’ light source, a less hazardous solvent system (trifluorotoluene) and faster reaction times. Using these conditions, the reaction scope has been expanded to include functionalised aldehyde and naphthoquinone substrates, affording the desired photo-products in acceptable to excellent yields (17–81%). Factors influencing the regiochemistry of the photo Friedel–Crafts reaction on unsymmetrical naphthoquinones have also been investigated.

  本文介绍了一种实用而可靠的萘醌光弗里德酰化反应。虽然该反应在阳光下进行得很慢，但优化后的条件与已报道的条件相比有了很大改进，因为它利用了更可靠、更实用的 "模拟太阳 "光源、危害更小的溶剂系统（三氟甲苯）以及更快的反应时间。利用这些条件，反应范围扩大到包括官能化醛和萘醌底物，以可接受到极好的收率（17%-81%）获得所需的光反应产物。此外，还研究了影响不对称萘醌的光弗里德卡夫斯反应的区域化学性质的因素。
• Total Synthesis and Structural Determination of XR774, a Tyrosine Kinase Inhibitor
  作者：Kuniaki Tatsuta、Daisuke Sekine、Shinichi Hayama、Yasuhiro Kataoka、Shinya Hayashi、Seijiro Hosokawa

  DOI：10.1021/acs.joc.7b02997

  日期：2018.7.6

  Total synthesis and structural determination of XR774 has been accomplished. The benzo[j]fluoranthene skeleton has been constructed by regioselective coupling between tetraline 3 and tetralone 4 successively followed by the sequential transformation including the Birch reduction to prepare allylic alcohol, simultaneous bromination of vinylic and aromatic moieties, and the nickel-mediated intramolecular

  XR774的总合成和结构测定已完成。苯并[ j ]荧蒽骨架是通过依次在四氢呋喃3和四氢萘酮4之间进行区域选择性偶联，然后依次转化（包括将桦木还原成烯丙基醇，乙烯基和芳香族部分同时溴化以及镍介导的分子内偶联反应）而构建的。。外消旋物17的光学分辨率导致（-）-XR774的第一全合成。
• Asymmetric Total Synthesis of PD-116740
  作者：Chaoying Zheng、Tao Xie、Haibing He、Shuanhu Gao

  DOI：10.1021/acs.orglett.0c03990

  日期：2021.1.15

  A new approach was developed to achieve the asymmetric total synthesis of (+)-PD-116740, an angucyclinone from the actinomycete isolate (WP 4669). A sequence of asymmetric dihydroxylation followed by oxidative cyclization was applied to stereoselectively construct the core trans-9,10-dihydrophenanthrene-9,10-diol B–C–D ring. A new Cu salt Cu(OH)OTf·NMI2 was found to be the best oxidant to induce the

  开发了一种新的方法来实现（+）-PD-116740的不对称全合成，PD-116740是一种来自放线菌分离物的环己酮（WP 4669）。一系列不对称的二羟基化反应和随后的氧化环化反应被用于立体选择性地构建核心的反式-9,10-二氢菲-9,10-二醇B–C–D环。发现新的铜盐Cu（OH）OTf·NMI 2是诱导氧化偶联和酚氧化的最佳氧化剂。
• Total synthesis of urdamycinone B via C-glycosidation of an unprotected sugar and Diels–Alder reaction of C-glycosyl juglone
  作者：Goh Matsuo、Yuko Miki、Masaya Nakata、Shuichi Matsumura、Kazunobu Toshima

  DOI：10.1039/cc9960000225

  日期：——

  The total synthesis of C-glycosyl angucycline, urdamycinone B 1, was achieved via C-glycosidation of naphthol 6 and the unprotected o-olivose 7, and Diels-Alder reaction of the unprotected C-glycosyl juglone 9 and the diene 17 as the key steps.
• Total Synthesis of <i>C</i>-Glycosylangucycline, Urdamycinone B, Using an Unprotected Sugar
  作者：Goh Matsuo、Yuko Miki、Masaya Nakata、Shuichi Matsumura、Kazunobu Toshima

  DOI：10.1021/jo990648y

  日期：1999.9.1

  The total synthesis of urdamycinone B (1), a prototypical member of the C-glycosylangucycline antibiotics, was achieved by a novel and effective strategy without any protecting group in the sugar moiety. The unprotected C-glycosyljuglone 6 was effectively synthesized by the aryl C-glycosidation of 1,5-naphthalenediol (16) with the totally unprotected D-olivose (8) and the subsequent regioselective photooxygenation of the resultant C-glycosylnaphthalenediol 17. On the other hand, the diene 7 was prepared from 3-methyl-2-cyclohexen-1-one (9) in a short step via the cross-coupling of the vinyl triflate 20 and vinylbutyltin (21) and the Wittig reaction of the aldehyde 24 and the phosphine 25. Finally, the regioselective Diels-Alder reaction of the unprotected C-glycosyljuglone 6 and the diene 7, followed by the regioselecitive introduction of the ketone function at the C1 position, led to the total synthesis of 1.