(R)-6-(6-bromohexyl)-2,2'-dimethoxy-1,1'-binaphthalenyl

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-6-(6-bromohexyl)-2,2'-dimethoxy-1,1'-binaphthalenyl
• 英文别名: 6-(6-Bromohexyl)-2-methoxy-1-(2-methoxynaphthalen-1-yl)naphthalene；6-(6-bromohexyl)-2-methoxy-1-(2-methoxynaphthalen-1-yl)naphthalene
• 化学式: C₂₈H₂₉BrO₂
• 分子量: 477.441
• InChiKey: YQTKPZXQBAUXMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-6-(6-bromohexyl)-2,2'-dimethoxy-1,1'-binaphthalenyl 在 硫脲 、 sodium hydroxide 、 碘 作用下， 以 二甲基亚砜 、 水 为溶剂， 反应 3.0h， 以69%的产率得到1,2-bis(6-(2,2'-dimethoxy-[1,1'-binaphthalen]-6-yl)hexyl)disulfane
  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：

  6-氯-6-氧代己酸乙酯 在 三乙基硅烷 、 lithium aluminium tetrahydride 、 三氯化铝 、 四溴化碳 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (R)-6-(6-bromohexyl)-2,2'-dimethoxy-1,1'-binaphthalenyl
  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.