2,2'-bis-(2-1H-indenyl)-1,1'-binaphthalene | 192203-10-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2'-bis-(2-1H-indenyl)-1,1'-binaphthalene
• 英文别名: 2-(1H-inden-2-yl)-1-[2-(1H-inden-2-yl)naphthalen-1-yl]naphthalene
• CAS: 192203-10-4
• 化学式: C₃₈H₂₆
• 分子量: 482.624
• InChiKey: BZLJSPUIJGLBBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  38
• 可旋转键数：
  3
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  titanium(III) chloride tetrahydrofuran 、 2,2'-bis-(2-1H-indenyl)-1,1'-binaphthalene 在 n-butyl lithium 、 H₂ 、 air 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以5%的产率得到ansa-[2,2'-bis(8-(bicyclo[4.3.0]-nona-1(6),7-dienyl))-1,1'-binaphthyl]dichlorotitanium
  参考文献：
  名称：

  Synthesis, structure, and properties of chiral titanium and zirconium complexes bearing biaryl strapped substituted cyclopentadienyl ligands

  摘要：

  The synthesis and characterization of 2,2'-bis(2-tetrahydroindenyl)biaryl metallocenes of titanium and zirconium which alleviate many of the stereochemical problems associated with previous ligand systems are described. Such systems give only a single chiral isomer of the complex, the biaryl link determines the chirality of the complex, and the tetrahydroindenyl ligands project their C2 chirality directly to the site of reaction. The reaction of the di-Grignard of o-bis(chloromethyl)benzene with the 2,2'-dimethyl esters of biphenyl, 6,6'-dimethylbiphenyl, and binaphthyl gave the corresponding bis(carbinols) in good yields. Acid catalyzed dehydrations of these diols gave the bis(2-indene) compounds in high yield. Both the racemic and the homochiral forms of the bis(2-indene) of the 6,6'-dimethylbiphenyl compound were prepared. Reaction of the dilithio anions of these indene compounds with TiCl3 and ZrCl4 gave the corresponding bis(indenyl) complexes which are sensitive to protic media and decomposed, in some cases rapidly, to the indene ligands. The protic sensitivity has been studied. The in situ prepared bis(2-indenyl) complexes are readily reduced with H-2 and Adam's catalyst to the tetrahydroindenyl complexes. The Ti(IV) and Zr(IV) tetrahydroindenyl complexes are stable in protic media. The yields of the complexes are generally good. X-ray diffraction structures for a bis(tetrahydroindenyl).0.5(hexane) and a bis(indenyl)metal complex (Ti(IV)) have been determined and confirm the expected structures.

  DOI：

  10.1021/om00035a026
• 作为产物：
  描述：

  2,2-二溴-1,1-联萘 、 2-茚酮 在 正丁基锂 、 对甲苯磺酸 作用下， 生成 2,2'-bis-(2-1H-indenyl)-1,1'-binaphthalene
  参考文献：
  名称：

  1,1'-联萘-2,2'-二基桥联的ansa-双（环戊二烯基）钛和-二氯化锆配合物的制备

  摘要：

  对映体富集的2,2'-二硫代-1,1'-联萘与各种环状环戊烯酮或2-茚满酮的偶联被证明是制备一系列环状双（环戊二烯）或双（茚）桥联反应的简便方法在对称的环戊二烯基位置上。六元或七元环状双（四氢茚）6或双（六氢氮杂烯）7配体可以容易地转化为钛或二氯化锆配合物。由于配体的对称性，只能形成茂金属二氯化物的单个C 2对称异构体。尽管环戊二烯基部分的表面是同位的，但手性桥强制茂金属配合物的手性构象。双（茚基）5或五元环状双（四氢戊烯）8配体不能被金属化。制备了未桥连的2-甲基和2-苯基取代的四氢戊二烯27和28，它们可以容易地转化为二氯化钛配合物。

  DOI：

  10.1016/s0022-328x(96)06635-1

文献信息

• Preparation of 1,1′-binaphthyl-2,2′-diyl bridged ansa-bis( annulated cyclopentadienyl) titanium and -zirconium dichloride complexes
  作者：Ronald L. Halterman、Timothy M. Ramsey

  DOI：10.1016/s0022-328x(96)06635-1

  日期：1997.3

  series of annulated bis(cyclopentadienes) or bis(indenes) bridged at a symmetrical cyclopentadienyl position. The six- or seven-membered annulated bis(tetrahydroindene) 6 or bis(hexahydroazulene) 7 ligands could readily be converted to titanium or zirconium dichloride complexes. Owing to the symmetry of the ligands, only a single C2-symmetrical isomer of the metallocene dichloride could form. Although

  对映体富集的2,2'-二硫代-1,1'-联萘与各种环状环戊烯酮或2-茚满酮的偶联被证明是制备一系列环状双（环戊二烯）或双（茚）桥联反应的简便方法在对称的环戊二烯基位置上。六元或七元环状双（四氢茚）6或双（六氢氮杂烯）7配体可以容易地转化为钛或二氯化锆配合物。由于配体的对称性，只能形成茂金属二氯化物的单个C 2对称异构体。尽管环戊二烯基部分的表面是同位的，但手性桥强制茂金属配合物的手性构象。双（茚基）5或五元环状双（四氢戊烯）8配体不能被金属化。制备了未桥连的2-甲基和2-苯基取代的四氢戊二烯27和28，它们可以容易地转化为二氯化钛配合物。
• Synthesis, structure, and properties of chiral titanium and zirconium complexes bearing biaryl strapped substituted cyclopentadienyl ligands
  作者：William W. Ellis、T. Keith Hollis、William Odenkirk、John Whelan、Robert Ostrander、Arnold L. Rheingold、B. Bosnich

  DOI：10.1021/om00035a026

  日期：1993.11

  The synthesis and characterization of 2,2'-bis(2-tetrahydroindenyl)biaryl metallocenes of titanium and zirconium which alleviate many of the stereochemical problems associated with previous ligand systems are described. Such systems give only a single chiral isomer of the complex, the biaryl link determines the chirality of the complex, and the tetrahydroindenyl ligands project their C2 chirality directly to the site of reaction. The reaction of the di-Grignard of o-bis(chloromethyl)benzene with the 2,2'-dimethyl esters of biphenyl, 6,6'-dimethylbiphenyl, and binaphthyl gave the corresponding bis(carbinols) in good yields. Acid catalyzed dehydrations of these diols gave the bis(2-indene) compounds in high yield. Both the racemic and the homochiral forms of the bis(2-indene) of the 6,6'-dimethylbiphenyl compound were prepared. Reaction of the dilithio anions of these indene compounds with TiCl3 and ZrCl4 gave the corresponding bis(indenyl) complexes which are sensitive to protic media and decomposed, in some cases rapidly, to the indene ligands. The protic sensitivity has been studied. The in situ prepared bis(2-indenyl) complexes are readily reduced with H-2 and Adam's catalyst to the tetrahydroindenyl complexes. The Ti(IV) and Zr(IV) tetrahydroindenyl complexes are stable in protic media. The yields of the complexes are generally good. X-ray diffraction structures for a bis(tetrahydroindenyl).0.5(hexane) and a bis(indenyl)metal complex (Ti(IV)) have been determined and confirm the expected structures.