(S)-(+)-7,7'-Dihydroxy-2,2'-dimethoxy-1,1'-binaphthyl

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-(+)-7,7'-Dihydroxy-2,2'-dimethoxy-1,1'-binaphthyl
• 英文别名: 8-(7-Hydroxy-2-methoxynaphthalen-1-yl)-7-methoxynaphthalen-2-ol
• 化学式: C₂₂H₁₈O₄
• 分子量: 346.383
• InChiKey: TXKXTRXAEPCXHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  (S)-(+)-7,7'-Dihydroxy-2,2'-dimethoxy-1,1'-binaphthyl 在 2-碘酰基苯甲酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以93%的产率得到(S)-2,2’-dimethoxy-[1,1’-binaphthalene]-7,7’,8,8’-tetraone
  参考文献：
  名称：

  Axial Chiral Bisbenzophenazines: Solid-State Self-Assembly via Halide Hydrogen Bonds Triggered by Linear Alkanes

  摘要：

  An axial chiral tetrachlorinated bisbenzo-[A]-phenazine has been discovered that undergoes an alkane-induced shift in the solid state from a disordered amorphous form to an ordered polycrystalline form. This phase transition is caused by the formation of pores that accommodate linear alkanes of varying lengths with a very strong affinity as judged by differential scanning calorimetry. Single crystal X-ray structure analysis revealed that a series of weak phenolic OH center dot center dot center dot Cl hydrogen bonds dictates the pore structure. These weak interactions can be disrupted mechanically, causing the material to revert to the amorphous form. Notably, the interchange between the amorphous and crystalline forms is readily reversible and is easily observed by characteristic colorimetric changes. Measurements via photoimage processing reveal that the degree of color change is dictated by the type of alkane employed.

  DOI：

  10.1021/ja506137j
• 作为产物：
  描述：

  2,7-二羟基萘 在 lithium hydroxide 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 123.0h， 生成 (S)-(+)-7,7'-Dihydroxy-2,2'-dimethoxy-1,1'-binaphthyl
  参考文献：
  名称：

  胆汁酸模板上的1,1'-联萘酚单元的非对映选择性合成

  摘要：

  据报道在1，1′-联萘-2，2′-二醇衍生物的不对称合成中使用7-脱氧胆酸作为手性模板。用CH（3）CN中的Mn（acac）（3）进行了化合物7和11的分子内偶联，从而分别制得了具有65％和> 99％非对映选择性的联萘酚产物8和12。在两种情况下，通过计算机模型研究预测了（S）异构体的主要形成。在化合物12的情况下证实了这一点。

  DOI：

  10.1021/jo000703z

文献信息

• Circularly Polarized Luminescence Liquids Based on Siloxybinaphthyls: Best Binaphthyl Dihedral Angle in the Excited State
  作者：Kazuto Takaishi、Tomoki Matsumoto、Miyu Kawataka、Tadashi Ema

  DOI：10.1002/anie.202101226

  日期：2021.4.26

  compounds remained liquid over a broad range of temperatures, down to −50 °C. Time‐dependent DFT calculations indicated that in the excited state, the binaphthyls adopt a transoid conformation with a small angle between the electric and magnetic transition dipole moments (θμ,m=77°), which is a key factor in their CPL activity. The best binaphthyl dihedral angle in the excited state is approximately 110°

  合成了一系列带有三烷基甲硅烷氧基（OSiR 3）的轴向手性1,1'-联萘基。其中，在7,7'-位具有OSiR 3基团且在2,2'-位具有甲基的1 a – c在室温下为液体，纯净的液体显示出圆偏振发光（CPL）（R =卜; Φ FL，液体= 0.21，|克LUM，液体| = 1.6×10 -3）。的| 克液体， | 价值是纯液体的最高值。这些化合物在低至−50°C的较宽温度范围内仍保持液态。随时间变化的DFT计算表明，在激发态下，双萘基采用transoid构象与电和磁跃迁偶极矩之间的小角度（θ μ，米= 77°），这是在它们的CPL活性的关键因素。处于激发态的最佳联萘二面角约为110°。
• Optically active diphosphine, transition metal complex containing the
  申请人：Takasago International Corporation

  公开号：US05789609A1

  公开（公告）日：1998-08-04

  Disclosed are an optically active diphosphine represented by formula: ##STR1## wherein R represents a lower alkyl group having 1 to 4 carbon atoms; Ar represents a phenyl group which may be substituted with a lower alkyl group having 1 to 4 carbon atoms and/or a lower alkoxy group having 1 to 4 carbon atoms, a transition metal complex containing the diphosphine as a ligand, and a process for producing an optically active .delta.-oxo-.alpha.-cyano ester using the transition metal complex as a catalyst.

  本发明涉及一种光学活性的二膦化合物，其表示为以下公式：##STR1## 其中R代表1至4个碳原子的低碳基团；Ar代表苯基，其可以被取代为1至4个碳原子的低碳基团和/或1至4个碳原子的低烷氧基团。本发明还涉及一种以该二膦化合物为配体的过渡金属配合物，以及一种使用该过渡金属配合物作为催化剂制备光学活性的δ-氧代-α-氰基酯的方法。
• Helical Chirality of Azobenzenes Induced by an Intramolecular Chiral Axis and Potential as Chiroptical Switches
  作者：Kazuto Takaishi、Masuki Kawamoto、Kazunori Tsubaki、Taniyuki Furuyama、Atsuya Muranaka、Masanobu Uchiyama

  DOI：10.1002/chem.201003087

  日期：2011.2.7

  Let's do the twist! Helical chirality of cis‐azobenzene moieties, (P) or (M), was induced and unified by intramolecular axial chirality (see scheme). The twist direction depended on the axial chirality and the azobenzene link position of binaphthyls, but was independent of substituted groups. Moreover, these dyads were useful as chiroptical switches.

  让我们开始吧！顺式-偶氮苯部分（P）或（M）的螺旋手性是由分子内轴向手性诱导并统一的（参见方案）。扭转方向取决于双萘基的轴向手性和偶氮苯连接位置，但与取代基无关。此外，这些二元组还可以用作按摩开关。
• Optically active diphosphine, transition metal complex containing the same, and process for producing optically active compound using the complex
  申请人：Takasago International Corporation

  公开号：EP0839818A1

  公开（公告）日：1998-05-06

  Disclosed are an optically active diphosphine represented by formula: wherein R represents a lower alkyl group having 1 to 4 carbon atoms; Ar represents a phenyl group which may be substituted with a lower alkyl group having 1 to 4 carbon atoms and/or a lower alkoxy group having 1 to 4 carbon atoms, a transition metal complex containing the diphosphine as a ligand, and a process for producing an optically active δ-oxo-α-cyano ester using the transition metal complex as a catalyst.

  本发明公开了一种由式表示的光学活性二膦： 其中 R 代表具有 1 至 4 个碳原子的低级烷基；Ar 代表可被具有 1 至 4 个碳原子的低级烷基和/或具有 1 至 4 个碳原子的低级烷氧基取代的苯基、 含有二膦作为配位体的过渡金属络合物，以及使用该过渡金属络合物作为催化剂生产光学活性 δ-氧代-α-氰基酯的工艺。
• Fusion of Photochromic Reaction and Synthetic Reaction: Photoassisted Cyclization to Highly Strained Chiral Azobenzenophanes
  作者：Kazuto Takaishi、Masuki Kawamoto、Atsuya Muranaka、Masanobu Uchiyama

  DOI：10.1021/ol300992d

  日期：2012.7.6

  A method for synthesizing highly strained cyclic structures by combining photochromic and synthetic reactions is described. Tightly linked azobenzene binaphthyl dyads (R)-4 and (R)-6 could not be obtained by conventional cyclization, but continuous application of photoirradiation, which induced (E)->(Z) isomerization of the azobenzene moiety, allowed the cyclization reaction to proceed, affording the desired chiral azobenzenophanes.