methyl 6’-bromo-2,2’-dihydroxy-1,1’-binaphthyl-3-carboxylate | 145372-05-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 6’-bromo-2,2’-dihydroxy-1,1’-binaphthyl-3-carboxylate
• 英文别名: Methyl 6'-bromo-2,2'-dihydroxy-1,1'-binaphthalene-3-carboxylate；methyl 6'-bromo-2,2'-dihydroxy-1,1'-binaphthyl-3-carboxylate；methyl 4-(6-bromo-2-hydroxynaphthalen-1-yl)-3-hydroxynaphthalene-2-carboxylate
• CAS: 145372-05-0
• 化学式: C₂₂H₁₅BrO₄
• 分子量: 423.263
• InChiKey: HZSCTGQYDRXEDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 methyl 6’-bromo-2,2’-dihydroxy-1,1’-binaphthyl-3-carboxylate 在 C.I.酸性橙108 、 copper dichloride 作用下， 以60%的产率得到1-oxo-2-methoxycarbonyl-11-bromo-13c-ethoxyl-1,13c-dihydroxyldibenzo[a,kl]xanthene
  参考文献：
  名称：

  Synthesis, characterization, cytotoxicity, a poptosis and cell cycle arrest of dibenzoxanthenes derivatives

  摘要：

  Two new dibenzoxanthenes compounds 1 and 2 have been synthesized and characterized by analytical and spectral methods. The crystal structure of compound 2 informs that the five rings of compound are almost planar. The DNA binding properties of two compounds were studied by absorption titration, viscosity measurement and luminescence. These results indicate that two compounds interact with calf thymus DNA through intercalative mode. Agarose gel electrophoresis experiment shows that PBR 322 DNA can be induced to cleave by two compounds under photoactivated condition. Compound 1 exhibits higher cytotoxicity than compound 2 toward MG-63, BEL-7402 and A549 cells. The apoptosis and cellular uptake of MG-63 cells were studied by fluorescence microscopy. Two compounds can also enhance the level of reactive oxygen species (ROS) and decrease the mitochondrial membrane potential. Compound 1 induces cell cycle arrest in G2/M phase and compound 2 induces cell cycle arrest in G0/G1 phase in MG-63. (C) 2014 Published by Elsevier B.V.

  DOI：

  10.1016/j.saa.2014.05.054
• 作为产物：
  描述：

  3-羟基-2-萘甲酸甲酯 、 6-溴-2-萘酚 在 Oxone 、 silver nitrate 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以65%的产率得到methyl 6’-bromo-2,2’-dihydroxy-1,1’-binaphthyl-3-carboxylate
  参考文献：
  名称：

  使用N-杂环碳-铜配合物的C1对称BINOL的合成

  摘要：

  Fucntionalizing BINOL：双- NHC 铜配合物可用于氧化的2-萘酚的耦合。使用缺电子的2-萘时，产品产量最高。富电子和贫电子2-萘之间可以进行混合偶合，以得到良好的混合产物收率。

  DOI：

  10.1002/chem.200901295

文献信息

• Synthesis of<i>C</i>₁-Symmetric BINOLs Employing N-Heterocyclic Carbene-Copper Complexes
  作者：Alain Grandbois、Marie-Ève Mayer、Marion Bédard、Shawn K. Collins、Typhène Michel

  DOI：10.1002/chem.200901295

  日期：2009.9.28

  Fucntionalizing BINOL: Bis‐NHCCu complexes can be used for the oxidative coupling of 2‐naphthols. Product yields are highest when using electron‐deficient 2‐naphthols. Mixed couplings between electron‐rich and electron‐poor 2‐naphthols can be conducted to give good yields of the mixed products.

  Fucntionalizing BINOL：双- NHC 铜配合物可用于氧化的2-萘酚的耦合。使用缺电子的2-萘时，产品产量最高。富电子和贫电子2-萘之间可以进行混合偶合，以得到良好的混合产物收率。
• The oxidative cross-coupling of substituted 2-naphthols, part I: The scope and limitations
  作者：Martin Hovorka、Radim Ščigel、Jana Gunterová、Miloš Tichý、Jiří Závada

  DOI：10.1016/s0040-4020(01)88318-6

  日期：1992.1

  Highly selective oxidative cross-coupling of differently substituted 2-naphthols mediated by Cu(II)-tert-butyl amine complexes is described. The “cross”-products are obtained in good to excellent yields and the selectivity up to ⪢90% is observed depending on the substitution of naphthol nuclei. The alternative procedures - the cross-coupling of free naphthols with CuCl(OMe) as well as the coupling

  描述了由Cu（II）-叔丁胺络合物介导的不同取代的2-萘的高选择性氧化交叉偶联。获得“交叉”产物的收率好至极好，并且根据萘酚核的取代，观察到高达⪢90％的选择性。还研究了替代程序-游离萘与CuCl（OMe）的交叉偶联以及萘甲酸钠与无水氯化铜（II）的偶联-。所有这些方法使对不对称取代的联萘酚的简单且高收率的获取成为可能。报道了通过在三乙酰纤维素上的液相色谱法成功地光学拆分了2,2'-二羟基-1,1'-联萘-3-羧酸甲酯，并随后与已知绝对构型的联萘酚衍生物进行了构型相关性。
• Kalinovskii, Russian Journal of General Chemistry, 1996, vol. 66, # 4, p. 657 - 659
  作者：Kalinovskii

  DOI：——

  日期：——
• Heterocoupling of 2-naphthols enabled by a copper–N-heterocyclic carbene complex
  作者：Michael Holtz-Mulholland、Mylène de Léséleuc、Shawn K. Collins

  DOI：10.1039/c3cc38675a

  日期：——

  The reactivity of a Cu catalyst for oxidative coupling is modulated by a small molecule additive, diethyl malonate, that slows over-oxidation of 2-naphthols. Efficient heterocoupling between electron-rich and electron-poor 2-naphthols/2-naphthylamines affords C1-symmetric BINOLs with yields ranging from 35–98%.

  氧化偶联铜催化剂的反应活性受小分子添加剂丙二酸二乙酯的调节，丙二酸二乙酯可减缓 2-萘酚的过度氧化。富电子和贫电子 2-萘酚/2-萘胺之间的高效异质偶联生成了 C1 对称的 BINOL，产率为 35%-98%。
• Synthesis, characterization, cytotoxicity, a poptosis and cell cycle arrest of dibenzoxanthenes derivatives
  作者：Xiu-Zhen Wang、Jun-Hua Yao、Guang-Bin Jiang、Ji Wang、Hong-Liang Huang、Yun-Jun Liu

  DOI：10.1016/j.saa.2014.05.054

  日期：2014.12

  Two new dibenzoxanthenes compounds 1 and 2 have been synthesized and characterized by analytical and spectral methods. The crystal structure of compound 2 informs that the five rings of compound are almost planar. The DNA binding properties of two compounds were studied by absorption titration, viscosity measurement and luminescence. These results indicate that two compounds interact with calf thymus DNA through intercalative mode. Agarose gel electrophoresis experiment shows that PBR 322 DNA can be induced to cleave by two compounds under photoactivated condition. Compound 1 exhibits higher cytotoxicity than compound 2 toward MG-63, BEL-7402 and A549 cells. The apoptosis and cellular uptake of MG-63 cells were studied by fluorescence microscopy. Two compounds can also enhance the level of reactive oxygen species (ROS) and decrease the mitochondrial membrane potential. Compound 1 induces cell cycle arrest in G2/M phase and compound 2 induces cell cycle arrest in G0/G1 phase in MG-63. (C) 2014 Published by Elsevier B.V.