dimethyl 8,8'-bis(benzyloxy)-2,2'-dihydroxy-1,1'-binaphthyl-3,3'-dicarboxylate | 1388807-07-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: dimethyl 8,8'-bis(benzyloxy)-2,2'-dihydroxy-1,1'-binaphthyl-3,3'-dicarboxylate
• 英文别名: Methyl 3-hydroxy-4-(2-hydroxy-3-methoxycarbonyl-8-phenylmethoxynaphthalen-1-yl)-5-phenylmethoxynaphthalene-2-carboxylate
• CAS: 1388807-07-5
• 化学式: C₃₈H₃₀O₈
• 分子量: 614.651
• InChiKey: MLMWBKVDDVHGOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  dimethyl 8,8'-bis(benzyloxy)-2,2'-dihydroxy-1,1'-binaphthyl-3,3'-dicarboxylate 在 [N,N'-bis(salicylidene)ethane-1,2-diaminato]cobalt(II) 、 palladium 10% on activated carbon 、 氢气 、 氧气 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 dimethyl 2,2'-dihydroxy-5,5',8,8'-tetraoxo-5,5',8,8'-tetrahydro-1,1'-binaphthyl-3,3'-dicarboxylate
  参考文献：
  名称：

  Selective Oxidation of 8,8′-Hydroxylated Binaphthols to Bis-spironaphthalenones or Binaphtho-para- and Binaphtho-ortho-quinones

  摘要：

  The selective oxidation of a series of functionalized 8,8'-hydroxylated binaphthols to binaphtho-para- and binaphtho-ortho-quinones has been realized using either a Co-salen catalyst or ortho-iodoxybenzoic acid. A unique spirocyclic bis-spironaphthalenone was also obtained in good yield via a phenyliodonium diacetate promoted oxidative dearomatization.

  DOI：

  10.1021/ol302195e
• 作为产物：
  描述：

  methyl 5-(benzyloxy)-3-hydroxy-2-naphthoate 在 [CuCl(OH)TMEDA] 、 氧气 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 4.5h， 以91%的产率得到dimethyl 8,8'-bis(benzyloxy)-2,2'-dihydroxy-1,1'-binaphthyl-3,3'-dicarboxylate
  参考文献：
  名称：

  (S)-Bisoranjidiol 的对映选择性全合成，一种轴向手性双蒽醌

  摘要：

  首次对映选择性全合成双蒽醌( S )-bisoranjidiol 和非天然区域异构体。该合成的关键特征包括受阻 8-取代 2-萘酚的不对称氧化联芳偶联、选择性对醌形成和区域选择性串联 Diels-Alder/芳构化反应。

  DOI：

  10.1021/ol3001365

文献信息

• Selective Oxidation of 8,8′-Hydroxylated Binaphthols to Bis-spironaphthalenones or Binaphtho-<i>para</i>- and Binaphtho-<i>ortho</i>-quinones
  作者：Erin E. Podlesny、Patrick J. Carroll、Marisa C. Kozlowski

  DOI：10.1021/ol302195e

  日期：2012.9.21

  The selective oxidation of a series of functionalized 8,8'-hydroxylated binaphthols to binaphtho-para- and binaphtho-ortho-quinones has been realized using either a Co-salen catalyst or ortho-iodoxybenzoic acid. A unique spirocyclic bis-spironaphthalenone was also obtained in good yield via a phenyliodonium diacetate promoted oxidative dearomatization.
• Enantioselective Total Synthesis of (<i>S</i>)-Bisoranjidiol, an Axially Chiral Bisanthraquinone
  作者：Erin E. Podlesny、Marisa C. Kozlowski

  DOI：10.1021/ol3001365

  日期：2012.3.16

  The first enantioselective total synthesis of the bisanthraquinone (S)-bisoranjidiol and an unnatural regioisomer has been accomplished. Key features of the synthesis include the asymmetric oxidative biaryl coupling of a hindered 8-substituted 2-naphthol, selective para-quinone formation, and regioselective tandem Diels–Alder/aromatization reactions.

  首次对映选择性全合成双蒽醌( S )-bisoranjidiol 和非天然区域异构体。该合成的关键特征包括受阻 8-取代 2-萘酚的不对称氧化联芳偶联、选择性对醌形成和区域选择性串联 Diels-Alder/芳构化反应。