(S)-2,2'-bis(methoxymethoxy)-5,6,7,8-tetrahydro-1,1'-binaphthyl

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (S)-2,2'-bis(methoxymethoxy)-5,6,7,8-tetrahydro-1,1'-binaphthyl
• 英文别名: 2-(Methoxymethoxy)-1-[2-(methoxymethoxy)-5,6,7,8-tetrahydronaphthalen-1-yl]naphthalene；2-(methoxymethoxy)-1-[2-(methoxymethoxy)-5,6,7,8-tetrahydronaphthalen-1-yl]naphthalene
• 化学式: C₂₄H₂₆O₄
• 分子量: 378.468
• InChiKey: HBIBRHSGUIUGRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2,2'-bis(methoxymethoxy)-5,6,7,8-tetrahydro-1,1'-binaphthyl 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以99%的产率得到(Ra)-5,6,7,8-tetrahydro-[1,1']binaphthalenyl-2,2'-diol
  参考文献：
  名称：

  The synthesis of a novel non-C2 symmetric H4-BINOL ligand and its application to titanium-catalyzed enantioselective addition of diethylzinc to aldehydes

  摘要：

  The synthesis of the novel non-C-2 symmetric ligand (R)-5,6,7,8-tetrahydro-1,1'-binaphthol has been achieved via partial reduction of 2,2'-bis(methoxymethoxy)-1,1'-binaphthyl with Raney Ni-Al alloy in dilute aqueous NaOH solution followed by hydrolysis with HCl. Its titanium complex was found to be an effective catalyst in the asymmetric addition of diethylzinc to a variety of aldehydes, leading to the formation of secondary alcohols in high yields with good to excellent enantioselectivities. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00413-4
• 作为产物：
  描述：

  (R)-(+)-2,2’-双(甲氧基甲氧基)-1,1’-联萘 在 sodium hydroxide 、 aluminum nickel 作用下， 以 异丙醇 为溶剂， 反应 24.0h， 以85%的产率得到(S)-2,2'-bis(methoxymethoxy)-5,6,7,8-tetrahydro-1,1'-binaphthyl
  参考文献：
  名称：

  The synthesis of a novel non-C2 symmetric H4-BINOL ligand and its application to titanium-catalyzed enantioselective addition of diethylzinc to aldehydes

  摘要：

  The synthesis of the novel non-C-2 symmetric ligand (R)-5,6,7,8-tetrahydro-1,1'-binaphthol has been achieved via partial reduction of 2,2'-bis(methoxymethoxy)-1,1'-binaphthyl with Raney Ni-Al alloy in dilute aqueous NaOH solution followed by hydrolysis with HCl. Its titanium complex was found to be an effective catalyst in the asymmetric addition of diethylzinc to a variety of aldehydes, leading to the formation of secondary alcohols in high yields with good to excellent enantioselectivities. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00413-4

文献信息

• 3,3′-Anisyl-Substituted BINOL, H₄BINOL, and H₈BINOL Ligands: Asymmetric Synthesis of Diverse Propargylic Alcohols and Their Ring-Closing Metathesis to Chiral Cycloalkenes
  作者：Yang Yue、Mark Turlington、Xiao-Qi Yu、Lin Pu

  DOI：10.1021/jo9018446

  日期：2009.11.20

  aldehydes. It catalyzed the reactions of alkyl propiolates with 88−99% ee; the reactions of phenylacetylene with 81−87% ee; the reactions of 4-phenyl-1-butyne, an alkyl alkyne, with 77−89% ee; and the reactions of trimethylsilylacetylene with 92−97% ee. The optically active propargylic alcohols generated from this catalytic asymmetric alkyne addition were observed to undergo efficient ring-closing-metathesis

  制备了一系列光学活性的BINOL，H 4 BINOL和H 8 BINOL衍生物。这些化合物与ZnEt 2和Ti（O i Pr）4结合用于在室温下催化炔烃与醛的不对称反应以生成手性炔丙醇。通过比较研究，发现3,3'-双茴香基取代的H 8 BINOL（S）-7已发现其是通常的对映选择性催化剂，其用于结构多样的末端炔烃与各种醛的反应。它催化了ee值为88-99％的丙酸烷基酯的反应。苯乙炔与ee为81-87％的反应; 4-苯基-1-丁炔，一种烷基炔，与77-89％ee的反应；和三甲基甲硅烷基乙炔与92-97％ee的反应。观察到由这种催化不对称炔烃加成产生的旋光性炔丙醇在Grubbs II催化剂的存在下进行了有效的闭环复分解（RCM）反应，生成了手性环烯烃。进一步发现，一些手性炔丙基醇进行了高度化学选择性的串联RCM氢化反应，同时保留了对映体纯度。