2,2'-bis(dichloromethylstannyl)-1,1'-binaphthyl | 131759-08-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2'-bis(dichloromethylstannyl)-1,1'-binaphthyl
• 英文别名: dichloro-[1-[2-[dichloro(methyl)stannyl]naphthalen-1-yl]naphthalen-2-yl]-methylstannane
• CAS: 131759-08-5；460067-95-2
• 化学式: C₂₂H₁₈Cl₄Sn₂
• 分子量: 661.617
• InChiKey: ARPATAXOFIMFFC-UHFFFAOYSA-J

计算性质

• 辛醇/水分配系数(LogP)：
  7.17
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  2,2'-bis(dichloromethylstannyl)-1,1'-binaphthyl 以89%的产率得到
  参考文献：
  名称：

  KRISHNAMURTI, RAMESH;KUIVILA, HENRY G.;SHAIK, NASEEM S.;ZUBIETA, JON, ORGANOMETALLICS, 10,(1991) N, C. 423-431

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2-二溴-1,1-联萘 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2,2'-bis(dichloromethylstannyl)-1,1'-binaphthyl
  参考文献：
  名称：

  Synthesis and chemistry of novel 2,2'-binaphthyl-substituted organotin Lewis acids

  摘要：

  The synthesis and chemistry of novel Lewis acids containing neutral tin-centered Lewis acidic groups at the 2- and 2'-positions of 1,1'-binaphthyl are described. (+/-)-2,2'-Dibromo-1,1'-binaphthyl (3) was converted to the dilithio derivative, which was treated with trimethyltin chloride to yield 2,2'-bis(trimethylstannyl)-1,1'-binaphthyl (4) in excellent yield. Compound 4 then underwent highly selective methyl-Sn cleavage in the redistribution reactions with methyltin trichloride and tin tetrachloride to afford 2,2'-bis(monochlorodimethylstannyl)- and 2,2'-bis(dichloromethylstannyl)-1,1'-binaphthyl, 2a and 2b, respectively. The chlorotins were then converted into the organotin triflates, 2c and 2d, by metathetic reactions with silver triflate. Interaction of the bis(dichlorotin) 2b and DMSO afforded a mono-DMSO (12) whose X-ray crystal structure revealed that coordination of DMSO occurred to one tin center and a chloride ligand from this tin had bridging interaction with the other tin moiety. An estimation of the equilibrium constant for the formation of 12 was obtained by Sn-119 NMR spectroscopy.

  DOI：

  10.1021/om00048a018

文献信息

• (<i>R</i>)-2,2′-Bis(stannyl)-1,1′-binaphthyls as a New Chiral Bis-Metallic Binaphthyl Catalyst
  作者：Takashi Hoshi、Hiroshi Shionoiri、Masayoshi Katano、Toshio Suzuki、Masayoshi Ando、Hisahiro Hagiwara

  DOI：10.1246/cl.2002.600

  日期：2002.6

  Dilithiation followed by bis-stannylation with Me3SnCl of (R)-2,2′-dibromo-1,1′-binaphthyl (2) and the subsequent redistribution reaction of resulting (R)-2,2′-bis(trimethylstannyl)-1,1′-binaphthyl (6) with SnCl4 gave the novel chiral Lewis acid catalyst (R)-2,2′-bis(dichloromethylstannyl)-1,1′-binaphthyl (4). The catalytic properties of 4 and its triflate 5 were investigated as the first chiral bis-metallic binaphthyl catalyst.

  用 Me3SnCl 对(R)-2,2′-二溴-1,1′-联萘(2)进行二硫化反应，然后用 SnCl4 对生成的(R)-2,2′-双(三甲基锡)-1,1′-联萘(6)进行再分配反应、2′-双(三甲基锡)-1,1′-联萘(6)与氯化锡进行再分配反应，得到新型手性路易斯酸催化剂(R)-2,2′-双(二氯甲基锡)-1,1′-联萘(4)。作为首个手性双金属双萘催化剂，研究了 4 及其三酸酯 5 的催化特性。