2,2'-bis(trimethylstannyl)-1,1'-binaphthyl | 194100-42-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2'-bis(trimethylstannyl)-1,1'-binaphthyl
• 英文别名: Trimethyl-[1-(2-trimethylstannylnaphthalen-1-yl)naphthalen-2-yl]stannane
• CAS: 194100-42-0
• 化学式: C₂₆H₃₀Sn₂
• 分子量: 579.944
• InChiKey: FFWJYJLALWIYJV-UHFFFAOYSA-N

物化性质

• 沸点：
  530.5±60.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.75
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,2'-bis(trimethylstannyl)-1,1'-binaphthyl 以 硝基甲烷 、 二氯甲烷 为溶剂， 生成 (+/-)-2,2'-bis(methyl{{(trifluoromethyl)sulfonyl}oxy}stannyl)-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
• 作为产物：
  描述：

  2,2-二溴-1,1-联萘 以87%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：

文献信息

• Synthesis and Structure of 2,2′ ‐Boryl‐, Germyl‐Silyl‐, and Stannyl‐Substituted 1,1′ ‐Binaphthyl Systems
  作者：Birgit Schilling、Dieter E. Kaufmann、Volkier Kaiser

  DOI：10.1002/cber.19971300718

  日期：1997.7

  path to the binaphthylmonoboronic acid ester 9 is opened up. A further increase in the quantity of electrophile also leads to the binaphthylbisboronic acid ester 12. The 2,2′-disubstituted silyl, germyl, and stannyl derivatives 13a-15a are accessible in good yields. Treatment with boron halides leads exclusively to methyl/halogen exchange, giving the bidentate Lewis acids 13b-15b, the former of which can

  通过2,2'-二溴-1,1'-联萘基（5）的锂化反应，合成了许多在2-或2,2'-位取代的路易斯酸联萘系统。逐步锂化并随后用硼酸三甲酯进行硼化，生成溴化硼酸6，可通过与频哪醇酯化7来稳定溴化硼酸。通过将反应混合物增加至2当量。正丁基锂和2当量 硼酸甲酯打开了通向二萘基单硼酸酯9的路径。亲电子试剂的量的进一步增加也导致了联萘基双硼酸酯12。2,2'-二取代的甲硅烷基，癸基和苯乙​​烯基衍生物13a-15a产量高。治疗卤化硼引线排他地涉及甲基/卤素交换，给予二齿路易斯酸13B-15B，其中前者可通过oxygen.Only在双（三丁基锡烷基）联萘的情况下，桥接16A不本位取代发生在存在三氯化硼，得到双（二氯硼基）取代的双萘基16b，然后可以将其水解为11。通过X射线衍射研究了大多数化合物的结构。对于2,2'-二取代的化合物13a-15a萘基彼此垂直取向。分子内和分子间的相互作用受该双萘基系统的控
• Synthesis of Bis(trimethylstannyl)aryl Compounds via an S_RN1 Mechanism with Intermediacy of Monosubstitution Products
  作者：Alicia B. Chopa、María T. Lockhart、Gustavo F. Silbestri

  DOI：10.1021/om020622o

  日期：2002.12.1

  ,1‘-binaphthyl (2), useful as intermediates in the preparation of bidentate Lewis acids, have been synthesized from simple phenols through a two-step sequence. Thus, 2-chlorophenol, 1,2-dihydroxybenzene, and binaphthol were converted into the corresponding aryl diethyl phosphate esters 4−6, which on reaction with sodium trimethylstannide (3) in liquid ammonia, under irradiation, afforded 1 and 2, respectively

  由简单的酚类合成了1,2-双（三甲基锡烷基）苯（1）和2,2'-双（三甲基锡烷基）-1,1'-联萘（2），它们可用作制备双齿路易斯酸的中间体。通过两步序列。因此，2-氯苯酚，1,2-二羟基苯，和联萘酚转化成相应的芳基二乙基磷酸酯4 - 6，其用trimethylstannide钠（反应3在液氨）照射下，得到1和2分别为，收率很高（66-82％）。获得的结果清楚地表明反应是通过S RN进行的一种机制，涉及一元替代产品的中介。
• (<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。
• Thermal Cyclodehydrogenations To Form 6-Membered Rings:  Cyclizations of [5]Helicenes
  作者：Xiang Xue、Lawrence T. Scott

  DOI：10.1021/ol7015516

  日期：2007.9.1

  Flash vacuum pyrolysis (FVP) of [5]helicene induces a thermal cyclodehydrogenation to form benzo[ghi]perylene. Evidence is presented that supports an electrocyclization-rearomatization mechanism and is inconsistent with mechanistic alternatives involving the intermediacy of aryl radicals or carbenes in the helicene fjord region.
• Synthesis and chemistry of novel 2,2'-binaphthyl-substituted organotin Lewis acids
  作者：Ramesh Krishnamurti、Henry G. Kuivila、Naseem S. Shaik、Jon Zubieta

  DOI：10.1021/om00048a018

  日期：1991.2

  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.