(R)-6-(hydroxymethyl)-2,2'-bis(methoxymethyloxy)-1,1'-binaphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-6-(hydroxymethyl)-2,2'-bis(methoxymethyloxy)-1,1'-binaphthalene
• 英文别名: (R)-(2,2'-bis(methoxymethoxy)-[1,1'-binaphthalen]-6-yl)methanol；(R)-6-hydroxymethyl-2,2'-bis(methoxymethoxy)-1,1'-binaphthalene；(2,2'-bis(methoxymethoxy)-[1,1'-binaphthalen]-6-yl)methanol；[6-(Methoxymethoxy)-5-[2-(methoxymethoxy)naphthalen-1-yl]naphthalen-2-yl]methanol；[6-(methoxymethoxy)-5-[2-(methoxymethoxy)naphthalen-1-yl]naphthalen-2-yl]methanol
• 化学式: C₂₅H₂₄O₅
• 分子量: 404.463
• InChiKey: XAIWMRVFUKWSMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-6-(hydroxymethyl)-2,2'-bis(methoxymethyloxy)-1,1'-binaphthalene 在 四溴化碳 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Synthesis of small palladium nanoparticles stabilized by bisphosphine BINAP bearing an alkyl chain and their palladium nanoparticle-catalyzed carbon–carbon coupling reactions under room-temperature

  摘要：

  研究发现，C8-BINAP 是一种有效的保护配体，可用于制备和稳定具有极小核尺寸和窄粒度分布的钯纳米粒子，C8-BINAP钯纳米粒子在室温下可作为碳碳偶联反应的高效催化剂。

  DOI：

  10.1039/b605390b
• 作为产物：
  描述：

  (R)-(+)-6,6`-二溴-2,2`-双(甲氧基亚甲氧基)-1,1`-联萘 在 sodium tetrahydroborate 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 8.5h， 生成 (R)-6-(hydroxymethyl)-2,2'-bis(methoxymethyloxy)-1,1'-binaphthalene
  参考文献：
  名称：

  Dendritic BINOL ligands for asymmetric catalysis: effect of the linking positions and generations of the dendritic wedges on catalyst properties

  摘要：

  Three types of new chiral BINOL ligands (2, 3 and 4) bearing dendritic wedges have been synthesized through coupling reaction between 3-hydroxymethyl-2,2'-bis(methoxymethyl)-1,1'-binaphthol (7), 6,6'-dihydroxymethyl-2,2'-bis(methoxymethyl)-1,1'-binaphthol (12), 6-hydroxymethyl-2,2'-bis(methoxymethyl)-1,1'-binaphthol (15) and Frechet-type polyether dendritic benzyl bromide, followed by deprotection of methoxymethyl groups by (PrOH)-Pr-i/HCl, respectively. These new ligands obtained were assessed in enantioselective Lewis acid-catalyzed addition of diethylzinc to benzaldehyde. Compared to the enantioselectivity observed with dendrimer 1 bearing the dendritic wedges at 3,3'-positions of the binaphthyl backbone, higher enantioselectivity for all these ligands was observed. Difference in the effect of linking positions and generations on enantioselectivity and/or activity for all three kinds of dendritic ligand-derived catalysts was observed. Among these dendritic ligands, (R)-3/Ti(IV) catalyst with the dendritic wedges at 6,6-positions of BINOL gave the highest enantioselectivity (up to 87% ee). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.030

文献信息

• Enantioselective Continuous-Flow Production of 3-Indolylmethanamines Mediated by an Immobilized Phosphoric Acid Catalyst
  作者：Laura Osorio-Planes、Carles Rodríguez-Escrich、Miquel A. Pericàs

  DOI：10.1002/chem.201303860

  日期：2014.2.17

  polystyrene‐supported 1,1’‐bi‐2‐naphthol derived phosphoric acid has been synthesized and applied in the enantioselective Friedel–Crafts reaction of indoles and sulfonylimines. The immobilized catalyst was highly active and selective, and gave rise to a broad range of 3‐indolylmethanamines (19 examples) in high yields and excellent enantioselectivities (up to 98 % enantiomeric excess) after short reaction

  合成了一种由聚苯乙烯支撑的1,1'-联-2-萘酚衍生的磷酸，并将其用于吲哚和磺酰亚胺的对映选择性Friedel-Crafts反应。固定化催化剂具有很高的活性和选择性，在非常方便的反应条件下（RT in二氯甲烷）。此外，可以进行重复回收（14个循环），而不会大幅降低催化性能，并且该系统可适应连续流操作（6小时）。最后，
• [EN] POLYMER SUPPORTED PHOSPHORIC ACIDS AND USE THEREOF AS CATALYSTS IN THE PREPARATION OF 3-INDOLYLMETHANAMINES<br/>[FR] ACIDES PHOSPHORIQUES SUPPORTÉS SUR POLYMÈRES ET LEUR UTILISATION EN TANT QUE CATALYSEURS DANS LA PRÉPARATION DE 3-INDOLYLMÉTHANAMINES
  申请人：FUNDACIÓ INST CATAL D INVESTIGACIÓ QUÍMICA ICIQ

  公开号：WO2015086793A1

  公开（公告）日：2015-06-18

  The present invention relates to the field of catalysis, more particularly to the field of organocatalysis and to polymer supported chiral phosphoric acid catalysts. It also relates to the use of these compounds in the preparation of chiral 3-indolylmethanamines Formula (I).

  本发明涉及催化领域，更具体地涉及有机催化领域和聚合物支持手性磷酸催化剂。它还涉及使用这些化合物制备手性3-吲哚甲胺式（I）的方法。
• Polymer supported phosphoric acids and use thereof as catalysts in the preparation of 3-indolylmethanamines
  申请人：Fundació Institut Català d'Investigació Química

  公开号：EP2883879A1

  公开（公告）日：2015-06-17

  The present invention relates to the field of catalysis, more particularly to the field of organocatalysis and to polymer supported chiral phosphoric acid catalysts. It also relates to the use of these compounds in the preparation of chiral 3-indolylmethanamines.

  本发明涉及催化领域，更具体地涉及有机催化和聚合物支持手性磷酸催化剂领域。它还涉及在制备手性3-吲哚甲胺类化合物中使用这些化合物。
• Synthesis of several polyethers derived from BINOL and their application in the asymmetric borane reduction of prochiral ketones
  作者：An-Lin Zhang、Zeng-da Yu、Li-Wen Yang、Nian-Fa Yang

  DOI：10.1016/j.tetasy.2014.12.012

  日期：2015.2

  Several novel epoxy monomers, (S,S)- or (S,R)-3-(glycidyloxy)methy1-2,2'-bis(methoxymethyloxy)-1, 1'-binaphthalene and (S,S)- or (S,R)-6-(glycidyloxy)methy1-2,2'-bis(methoxymethyloxy)-1,1'-binaphthalene, which were derived from chiral BINOL and epichlorohydrin, were synthesized and underwent anionic polymerization and deprotection of the MOM groups to obtain soluble polyethers. These polyethers were used to induce the enantioselective borane reduction of prochiral ketones. The substrates gave up to 98% yield with over 99% ee values. The recovered polyethers could be reused many times to induce the enantioselective reduction of prochiral ketones without losing their enantioselective induction ability. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis and catalytic applications of soluble polymer-supported BINOL
  作者：Doss Jayaprakash、Hiroaki Sasai

  DOI：10.1016/s0957-4166(01)00443-8

  日期：2001.10

  The synthesis of a soluble polymer containing BINOL residues is described. Titanium-BINO Late and AlLibis(binaphthoxide) catalysts are easily generated from this polymer and applied to the asymmetric reaction of Et2Zn with benzaldehyde and the asymmetric Michael addition. respectively. The products are obtained in good yields with high enantioselectivities. (C) 2001 Elsevier Science Ltd. All rights reserved.