dimethyl 2,2'-dimethoxy-1,1'-bunaphthalene-3,3'-dicarboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: dimethyl 2,2'-dimethoxy-1,1'-bunaphthalene-3,3'-dicarboxylate
• 英文别名: (S)-dimethyl-2,2'-dimethoxy-1,1'-binaphthalene-3,3'-dicarboxylate；3-Methoxy-4-(2-methoxy-3-methoxycarbonyl-1-naphthalenyl)-2-naphthalenecarboxylic acid methyl ester；methyl 3-methoxy-4-(2-methoxy-3-methoxycarbonylnaphthalen-1-yl)naphthalene-2-carboxylate
• 化学式: C₂₆H₂₂O₆
• 分子量: 430.457
• InChiKey: NWULKMYMWPIZAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 2,2'-dimethoxy-1,1'-bunaphthalene-3,3'-dicarboxylate 在 氢氧化钾 、 硼烷四氢呋喃络合物 、 四氯化锡 、 silver(l) oxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 29.0h， 生成 4-[3,6-bis(2-hydroxyethoxymethyl)-2-methoxynaphthalen-1-yl]-3-methoxynaphthalene-2-carboxylic acid
  参考文献：
  名称：

  Axially Chiral Synthons for Dendrimer Synthesis

  摘要：

  基于2,2'-二羟基-1,1'-联萘-3,3'-二羧酸的手性树状分子构建，制备了轴向手性合成单元，包括手性连接单元（3、6、8）、手性分支单元（10、12、14）和手性表面单元（5、17）。还研究了甲基3'-乙酰氧甲基-2,2'-二甲氧基-1,1'-联萘-3-羧酸甲酯（7）的区域选择性氯甲基化。

  DOI：

  10.1135/cccc19970925
• 作为产物：
  描述：

  2-羟基-3-萘甲酸 在 三氯化铁 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 dimethyl 2,2'-dimethoxy-1,1'-bunaphthalene-3,3'-dicarboxylate
  参考文献：
  名称：

  Axially Chiral Synthons for Dendrimer Synthesis

  摘要：

  基于2,2'-二羟基-1,1'-联萘-3,3'-二羧酸的手性树状分子构建，制备了轴向手性合成单元，包括手性连接单元（3、6、8）、手性分支单元（10、12、14）和手性表面单元（5、17）。还研究了甲基3'-乙酰氧甲基-2,2'-二甲氧基-1,1'-联萘-3-羧酸甲酯（7）的区域选择性氯甲基化。

  DOI：

  10.1135/cccc19970925

文献信息

• Conformationally rigid aromatic amino acids as potential building blocks for abiotic foldamers
  作者：Veera V. E. Ramesh、Arup Roy、Kuruppanthara N. Vijayadas、Amol M. Kendhale、Panchami Prabhakaran、Rajesh Gonnade、Vedavati G. Puranik、Gangadhar J. Sanjayan

  DOI：10.1039/c0ob00593b

  日期：——

  This communication describes the development of conformationally constrained unnatural aromatic amino acids, constructed on rigid backbone wherein the carboxyl and amino groups project in two dimensions (planes) on the aromatic framework. Such a feature offers the possibility of design and development of conformationally ordered synthetic oligomers with intriguing structural architectures distinct from those classically observed. Furthermore, such amino acids will have the potential to extend the conformational space available for foldamer design with diverse backbone conformation and structural architectures.

  该通讯描述了构象受限的非天然芳香族氨基酸的开发，该氨基酸构建在刚性主链上，其中羧基和氨基在芳香族框架上以二维（平面）投影。这一特征提供了设计和开发构象有序的合成低聚物的可能性，这些低聚物具有与经典观察到的结构不同的有趣结构。此外，此类氨基酸将有可能扩展可用于具有不同主链构象和结构体系的折叠体设计的构象空间。
• Moneta, W.; Baret, P.; Pierre, J.-L., Bulletin de la Societe Chimique de France, 1988, # 6, p. 995 - 1004
  作者：Moneta, W.、Baret, P.、Pierre, J.-L.

  DOI：——

  日期：——
• Enantioselective Synthesis of Binaphthol Derivatives by Oxidative Coupling of Naphthol Derivatives Catalyzed by Chiral Diamine·Copper Complexes
  作者：Makoto Nakajima、Irie Miyoshi、Kumiko Kanayama、Shun-ichi Hashimoto、Masahiro Noji、Kenji Koga

  DOI：10.1021/jo981808t

  日期：1999.4.1

  A highly efficient process of aerobic oxidative coupling of 2-naphthol derivatives catalyzed by 1 mol % of Cu(OH)Cl.TMEDA has been developed, Enantioselective oxidative coupling of naphthols was achieved by the use of 10 mol % of chiral catalysts prepared from proline-derived diamines and cuprous chloride, affording the corresponding binaphthols in good enantioselectivities of up to 78% ee. The ester moiety at the 3-position of the substrate was found to be essential for the good asymmetric induction observed in the present coupling reaction.
• Control of the Helical Chirality in Octahedral Complexes by a Chiral Macrobicyclic Cavity Possessing Six Convergent Hydroxyl Groups
  作者：Paul Baret、Virginie Beaujolais、Didier Gaude、Christian Coulombeau、Jean-Louis Pierre

  DOI：10.1002/chem.19970030619

  日期：1997.6

  AbstractThe (aR, aR, aR) and (aS, aS, aS) enantiomers of a chiral macrobicyclic ligand with a bicapped tris(binaphthol) structure were synthesized. Complexation of gallium(III), chromium(III) and iron(III) centres in the chiral cavities of these two ligands yielded exclusively one octahedral configuration in each case: the (aR, aR, aR) enantiomer gave a A complex and the (aS, aS, aS) enantiomer a complex. These assignments were established by CD spectroscopy for chromium and iron centres and by molecular modelling.
• Self-Assembly of Chiral Metallacycles and Metallacages from a Directionally Adaptable BINOL-Derived Donor
  作者：Yang Ye、Timothy R. Cook、Shu-Ping Wang、Jing Wu、Shijun Li、Peter J. Stang

  DOI：10.1021/jacs.5b07529

  日期：2015.9.23

  We present the formation of a series of chiral metallacydes and metallacages by the use of a BINOL-derived dicarbox-ylate as a donor that is capable of affording a variety of coordination angles between its two Lewis basic sites. Two squares, two rhomboids, two tetragonal prisms, and one hexagonal prism were successfully formed when the chiral dicarboxylate donor self-assembled with one of four ditopic Pt(II) complexes, including two bimetallic 180 degrees Pt-based acceptors, a 120 degrees bimetallic Pt-based acceptor, and a 90 degrees mononuclear Ptbased acceptor. Their structures were well characterized by P-31H-1} NMR, ESI-MS, CD, and optical rotation analyses.