(R)-4-(2,2'-dimethoxy-1,1'-binaphth-6-yl)butan-1-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-4-(2,2'-dimethoxy-1,1'-binaphth-6-yl)butan-1-ol
• 英文别名: 4-[6-Methoxy-5-(2-methoxynaphthalen-1-yl)naphthalen-2-yl]butan-1-ol；4-[6-methoxy-5-(2-methoxynaphthalen-1-yl)naphthalen-2-yl]butan-1-ol
• 化学式: C₂₆H₂₆O₃
• 分子量: 386.491
• InChiKey: CQFJBBBFGXYXEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-4-(2,2'-dimethoxy-1,1'-binaphth-6-yl)butan-1-ol 在 四溴化碳 、 硫脲 、 三苯基膦 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Development of new methods toward efficient immobilization of chiral catalysts

  摘要：

  BINOL moieties are efficiently immobilized onto the surface of a micelle-derived spherical polymer and a monolayer-protected Au cluster (Au-MPC). Ti-BINOLate complexes generated from the BINOL immobilized polymer and Au-MPC are found to promote catalytic asymmetric alkylation of benzaldehyde with Et2Zn to afford the adduct in up to 84% ee and 86% ee, respectively. Au-MPC-supported multicomponent asymmetric catalyst was prepared and used in the Michael reaction of 2-cyclohexen- 1-one with dibenzyl malonate affording the adduct in up to 67% yield and 98% ee. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.018
• 作为产物：
  描述：

  (R)-ethyl 4-(2,2'-dimethoxy-1,1'-binaphth-6-yl)butanoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到(R)-4-(2,2'-dimethoxy-1,1'-binaphth-6-yl)butan-1-ol
  参考文献：
  名称：

  Monolayer-Protected Au Cluster (MPC)-Supported Ti−BINOLate Complex

  摘要：

  Disulfides bearing (R)-1,1'-bi-2-naphthol ((R)-BINOL) moieties at each terminal position have been successfully introduced on the surface of Au cluster. Ti-BINOLate complex generated from the obtained monolayer-protected Au cluster (MPC) promoted catalytic asymmetric alkylation of benzaldehyde with Et2Zn to afford the adduct in up to 98% yield with 86% ee. After completion of the reaction, the BINOL-functionalized MPC was easily recovered.

  DOI：

  10.1021/ol035706n

文献信息

• Monolayer-Protected Au Cluster (MPC)-Supported Ti−BINOLate Complex
  作者：Kazuyoshi Marubayashi、Shinobu Takizawa、Tetsuo Kawakusu、Takayoshi Arai、Hiroaki Sasai

  DOI：10.1021/ol035706n

  日期：2003.11.1

  Disulfides bearing (R)-1,1'-bi-2-naphthol ((R)-BINOL) moieties at each terminal position have been successfully introduced on the surface of Au cluster. Ti-BINOLate complex generated from the obtained monolayer-protected Au cluster (MPC) promoted catalytic asymmetric alkylation of benzaldehyde with Et2Zn to afford the adduct in up to 98% yield with 86% ee. After completion of the reaction, the BINOL-functionalized MPC was easily recovered.
• Development of new methods toward efficient immobilization of chiral catalysts
  作者：Shinobu Takizawa、Mahesh L. Patil、Kazuyoshi Marubayashi、Hiroaki Sasai

  DOI：10.1016/j.tet.2007.03.018

  日期：2007.7

  BINOL moieties are efficiently immobilized onto the surface of a micelle-derived spherical polymer and a monolayer-protected Au cluster (Au-MPC). Ti-BINOLate complexes generated from the BINOL immobilized polymer and Au-MPC are found to promote catalytic asymmetric alkylation of benzaldehyde with Et2Zn to afford the adduct in up to 84% ee and 86% ee, respectively. Au-MPC-supported multicomponent asymmetric catalyst was prepared and used in the Michael reaction of 2-cyclohexen- 1-one with dibenzyl malonate affording the adduct in up to 67% yield and 98% ee. (c) 2007 Elsevier Ltd. All rights reserved.