2,2'-Bis-triisopropylsilanyloxy-[1,1']binaphthalenyl-6,6'-diol | 312911-15-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2'-Bis-triisopropylsilanyloxy-[1,1']binaphthalenyl-6,6'-diol
• CAS: 312911-15-2；210036-15-0
• 化学式: C₃₈H₅₄O₄Si₂
• 分子量: 631.015
• InChiKey: PVFFDIMKGQJQEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.18
• 重原子数：
  44.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,2'-Bis-triisopropylsilanyloxy-[1,1']binaphthalenyl-6,6'-diol 在 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 6,6'-Bis-(3,5-bis-benzyloxy-benzyloxy)-[1,1']binaphthalenyl-2,2'-diol
  参考文献：
  名称：

  光学活性树枝状联萘酚及其金属配合物的不对称催化合成

  摘要：

  通过6,6'-二羟基-2,2'-联萘酚和树枝状苄基溴的碱促进反应，合成了在6,6-位带有树状取代基的旋光联萘酚。尽管存在大量的树枝状取代基，但发现树枝状联萘酚形成金属络合物并催化不对称的CC键形成反应。

  DOI：

  10.1016/s0040-4039(98)00616-9
• 作为产物：
  描述：

  三异丙基氯硅烷 在 咪唑 、 盐酸 、 硼酸三甲酯 、 双氧水 、 叔丁基锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 150.0h， 生成 2,2'-Bis-triisopropylsilanyloxy-[1,1']binaphthalenyl-6,6'-diol
  参考文献：
  名称：

  光学活性树枝状联萘酚及其金属配合物的不对称催化合成

  摘要：

  通过6,6'-二羟基-2,2'-联萘酚和树枝状苄基溴的碱促进反应，合成了在6,6-位带有树状取代基的旋光联萘酚。尽管存在大量的树枝状取代基，但发现树枝状联萘酚形成金属络合物并催化不对称的CC键形成反应。

  DOI：

  10.1016/s0040-4039(98)00616-9

文献信息

• Immobilization of BINOL by Cross-Linking Copolymerization of Styryl Derivatives with Styrene, and Applications in Enantioselective Ti and Al Lewis Acid Mediated Additions of Et2Zn and Me3SiCN to Aldehydes and of Diphenyl Nitrone to Enol Ethers
  作者：Holger Sellner、Claude Faber、P. Beat Rheiner、Dieter Seebach

  DOI：10.1002/1521-3765(20001016)6:20<3692::aid-chem3692>3.0.co;2-0

  日期：2000.10.16

  The chiral ligand 1,1'-bi-2-naphthol (BINOL) has been succesfully immobilized on polystyrene. Several dendritic and non-dendritic BINOL derivatives (3, and 13-17), bearing at least two polymerizable styryl groups, were prepared and fully characterized. Suspension copolymerization of the MOM- or TIPS-protected cross-linking BINOL ligands (MOM = methyloxymethyl, TIPS = triisopropylsilyl) with styrene, cleavage of the protecting-groups, and loading with a Lewis-acid afforded catalytically active polystyrene-supported BINOLates. The polymer-bound BINOLs p-3, and p-13-p-16 were tested in the Ti-BINOLate-mediated addition of Et2Zn to PhCHO. The enantioselectivities (up to 93%) and conversions obtained with the polymer-bound catalysts were in most cases identical (within experimental error) to those obtained with the unsubstituted 1,1'-bi-2-naphthol and with the non-polymerized BINOL cross-linkers under homogeneous conditions. Special focus was put on the reusability of the supported catalyst: the polymer-beads were used in up to 20 consecutive catalytic runs, with the best polymers showing no or only minor loss of selectivity. BINOL-polymers p-17, obtained by copolymerization of a 3,3'-distyryl-substituted BINOL 17a with styrene, were used in the BINOL AlMe-mediated cycloaddition of diphenyl nitrone with alkyl vinyl ethers. In all cases the exolendo selectivity (greater than or equal to 92:8) and the enantioselectivities with which the exo-cycloadducts were formed (greater than or equal to 95%) correspond to those observed in the homogeneous reactions. A dendritically cross-linked BINOL-polymer was also employed in the Ti-BINOLate-mediated cyanosilylation of pivalaldehyde. The enantiopurity of the cyanohydrine obtained in the first run was as high as in the homogeneous reaction (72%); surprisingly the catalytic performance of the supported catalyst increased steadily during the first catalytic cycles to reach 83%. Thus, cross-linking BINOLs can be succesfully incorporated into a polystyrene matrix (without racemization!) to give poly mer-bound BINOL ligands that give excellent performance over many catalytic cycles with catalytic activities comparable with those of soluble analogues.
• Synthesis of optically active dendritic binaphthols and their metal complexes for asymmetric catalysis
  作者：Shigeru Yamago、Makoto Furukawa、Akira Azuma、Jun-ichi Yoshida

  DOI：10.1016/s0040-4039(98)00616-9

  日期：1998.5

  Optically active binaphthols bearing dendritic substituents at the 6,6-positions were synthesized by the base promoted reaction of 6,6′-dihydroxyl-2,2′-binaphthol and the dendritic benzyl bromides. Despite the bulky dendritic substituents, the dendritic binaphthols were found to form metal complexes and catalyze asymmetric CC bond forming reactions.

  通过6,6'-二羟基-2,2'-联萘酚和树枝状苄基溴的碱促进反应，合成了在6,6-位带有树状取代基的旋光联萘酚。尽管存在大量的树枝状取代基，但发现树枝状联萘酚形成金属络合物并催化不对称的CC键形成反应。