5-Methoxymethoxy-naphthalene-1,4-diol | 176040-43-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-Methoxymethoxy-naphthalene-1,4-diol
• 英文别名: 5-(Methoxymethoxy)naphthalene-1,4-diol
• CAS: 176040-43-0
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: AXGWHABPJUTNCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Methoxymethoxy-naphthalene-1,4-diol 在 palladium on activated charcoal 三氟甲磺酸三甲基硅酯 、 氢气 、 sodium hydride 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.0h， 生成 6-[(2R,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]-5-hydroxynaphthalene-1,4-dione
  参考文献：
  名称：

  Total Synthesis of C-Glycosylangucycline, Urdamycinone B, Using an Unprotected Sugar

  摘要：

  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.

  DOI：

  10.1021/jo990648y
• 作为产物：
  描述：

  5-羟基对萘醌 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 1.0h， 生成 5-Methoxymethoxy-naphthalene-1,4-diol
  参考文献：
  名称：

  Total Synthesis of C-Glycosylangucycline, Urdamycinone B, Using an Unprotected Sugar

  摘要：

  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.

  DOI：

  10.1021/jo990648y

文献信息

• 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.