2-iodo-2'-methyl-1,1'-binaphthyl | 402718-90-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-iodo-2'-methyl-1,1'-binaphthyl
• 英文别名: 1-(2-Iodonaphthalen-1-yl)-2-methylnaphthalene
• CAS: 402718-90-5
• 化学式: C₂₁H₁₅I
• 分子量: 394.255
• InChiKey: LRRCBNQUDRPWFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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-iodo-2'-methyl-1,1'-binaphthyl 在 sodium perborate 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of Chiral Diaryliodonium Salts, 1,1‘-Binaphthyl-2-yl(phenyl)iodonium Tetrafluoroborates:  Asymmetric α-Phenylation of β-Keto Ester Enolates

  摘要：

  DOI：

  10.1021/ja992236c
• 作为产物：
  描述：

  (S)-2-bromo-2'-methyl-1,1'-binaphthyl 在 碘 作用下， 生成 2-iodo-2'-methyl-1,1'-binaphthyl
  参考文献：
  名称：

  Synthesis of Chiral Diaryliodonium Salts, 1,1‘-Binaphthyl-2-yl(phenyl)iodonium Tetrafluoroborates:  Asymmetric α-Phenylation of β-Keto Ester Enolates

  摘要：

  DOI：

  10.1021/ja992236c

文献信息

• Catalytic Asymmetric Vinylation of Ketone Enolates
  作者：André Chieffi、Ken Kamikawa、Jens Åhman、Joseph M. Fox、Stephen L. Buchwald

  DOI：10.1021/ol0159470

  日期：2001.6.1

  [see reaction]. A protocol for the catalytic asymmetric vinylation of ketone enolates has been developed. Key to the success of this process was the development of new electron-rich chiral monodentate ligands.

  [请参阅反应]。已开发出一种用于酮烯醇酯催化不对称乙烯基化的方案。该方法成功的关键是开发新的富含电子的手性单齿配体。
• Study on the synthesis of nonracemic C2-symmetric 1,1′-binaphthyl-2,2′-diyl bridged ferrocene. Stereochemical result of the cross-coupling reactions controlled by Pd(II) or Pd(IV) complex intermediacy
  作者：P Kasák、R Mikláš、M Putala

  DOI：10.1016/s0022-328x(01)00926-3

  日期：2001.12

  Palladium catalyzed Negishi, Suzuki and Stille cross-coupling reactions of enantiopure 2,2′-diiodo-1,1′-binaphthyl with the corresponding 1,1′-dimetalloferrocenes gave the C2-symmetric binaphthyl bridged ferrocene 1-1,1′-(1,1′-binaphthyl-2,2′-diyl)ferrocene (1). The latter was obtained by Stille coupling with the bis(trimethylstannyl) derivative but not with the bis(tributylstannyl) one. Products of

  钯催化对映纯2,2'-二碘-1,1'-联萘与相应的1,1'-双金属二茂铁的Negishi，Suzuki和Stille交叉偶联反应，得到C 2对称的双萘桥联二茂铁1-1,1' -（1,1'-联萘-2,2'-二基）二茂铁（1）。后者是通过Stille与双（三甲基锡烷基）衍生物偶联而未与双（三丁基锡烷基）衍生物偶联而获得的。在这两种情况下，都获得了从锡到双萘基的烷基转移产物。这些在1，1′-联萘的2和2′位上的交叉偶联反应的立体化学结果取决于1，1′-双金属二茂铁的反应性。Negishi偶联以立体保守的方式进行（提供对映纯产品1）。在与反应性较低的硼和锡有机金属化合物反应期间，发生了联萘基部分的完全消旋。提议的不同反应途径包括前者中的C 1对称钯（II）中间体和后者情况中的构型不稳定的C 2对称钯（IV）环状中间体。与交叉偶联反应相反，二茂铁与对映纯1,1'-联萘-2,2'-双重氮盐的自由基芳基
• Intramolecularly Sulfur-Stabilized Silicon Cations with Chiral Binaphthyl Backbones: Synthesis of Three Different Motifs and Their Application in Enantioselective Diels–Alder Reactions
  作者：Volker H. G. Rohde、Maria F. Müller、Martin Oestreich

  DOI：10.1021/acs.organomet.5b00351

  日期：2015.7.13

  The formation and Si-29 NMR spectroscopic characterization of silicon cations that are intramolecularly stabilized by a dialkeyl thioether are described. The chemical stability of the silicon sulfur Lewis pair and, hence, the viability Of the approach, were probed with a 2-[(alkylthio)methyl]phenyl-substituted hydrosilane as a proxy before three different motifs with chiral binaphthyl backbones were prepared in multistep sequences. The degree of shielding of the silicon atom in these cations was found to depend on the substitution pattern at the silicon atom and the ring size generated by the silicon sulfur interaction: These sulfur-stabilized silicon cations are sufficiently reactive to promote Diels-Alder reactions of cyclohexa-1,3-diene with various dienophiles; the same set of reactions with cyclopentadiene is also reported. One of the three chiral Lewis acids induces low, but promising, enantioselectivity, and 24% ee is the highest Value so far obtained with a cationic tetracoordinate silicon catalyst.