(Sa)-2-(N,N-diethylthiocarbamoyloxy)-2'-hydroxy-1,1'-binaphthyl

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Sa)-2-(N,N-diethylthiocarbamoyloxy)-2'-hydroxy-1,1'-binaphthyl
• 英文别名: O-[1-(2-hydroxynaphthalen-1-yl)naphthalen-2-yl] N,N-diethylcarbamothioate
• 化学式: C₂₅H₂₃NO₂S
• 分子量: 401.529
• InChiKey: HHMJNMJBNDBOOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  64.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  S-1,1'-联-2-萘酚 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 (Sa)-2-(N,N-diethylthiocarbamoyloxy)-2'-hydroxy-1,1'-binaphthyl
  参考文献：
  名称：

  Preparation of silane-grafted pellets: silica bound reagents in a very convenient form

  摘要：

  High surface area silica pellets are excellent supports for the preparation of silica supported reagents and solid-phase basal linkers through reaction with (RO)(3)Si(CH2)(3)FG (FG=NH2, NHMe, Cl, NHC(=O)NH2, OC(=O)CMe(=CH2), NCO, NEt2). High loadings (0.66-2.15 mmol g(-1)) of grafted silane materials are realised at synthetically useful loadings per pellet (ca. 0.06 mmol). Preliminary trials show that trial linker chemistry and ligand synthesis can be carried out on these materials and that these reactions can be monitored by solid state C-13 NMR studies on individual pellets. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.140

文献信息

• Copper-Catalysed Asymmetric Conjugate Addition of Organometallic Reagents to Linear Enones
  作者：Simon M.W Bennett、Stephen M Brown、Anthony Cunningham、Michael R Dennis、James P Muxworthy、Michael A Oakley、Simon Woodward

  DOI：10.1016/s0040-4020(00)00140-x

  日期：2000.4

  Methods for enantioselective 1,4-addition of main-group organometallics to linear enones are overviewed. Thiourethane and thioether 1,1′-binaphthyl-based ligands are effective for copper-catalysed 1,4-addition of ZnEt2 and AlR3 (R=Me, Et) to trans-alkyl-3-en-2-ones; enantioselectivities of up to 72% e.e. are attained. In comparison 1,4-addition of ZnEt2 to 2-cyclohexenone proceeds in up to 77% e.e

  概述了将主族有机金属与线性烯酮进行对映选择性1,4-加成的方法。硫代氨基甲酸酯和硫醚1,1'-联萘基配体对ZnEt 2和AlR 3（R = Me，Et）的铜催化1,4-加成反应生成反-烷基-3-en-2- one有效。对映选择性高达ee的72％。相比之下，在具有相同配体家族的情况下，ZnEt 2向2-环己烯酮的1,4-加成反应最多可产生77％ee。
• Copper-catalysed asymmetric conjugate addition of organometallic reagents to linear enones using thiourethane ligands
  作者：Simon M.W. Bennett、Stephen M. Brown、James P. Muxworthy、Simon Woodward

  DOI：10.1016/s0040-4039(98)02686-0

  日期：1999.2

  In the presence of chiral thiourethane ligands [Cu(MeCN)4]BF4 forms active catalysts for the conjugate addition of MeMgBr, ZnEt2 and AlR3 (R = Me, Et) to non-3-en-2-one, hept-3-en-2-one, and 5-methylhex-3-en-2-one. Enantioselectivities of up to 51% are realised for these difficult substrates; for cyclohex-2-enone an e.e. of 42% is attained.

  在手性硫代氨基​​甲酸酯配体的存在下[Cu（MeCN）4 ] BF 4形成活性催化剂，用于将MeMgBr，ZnEt 2和AlR 3（R = Me，Et）共轭加成到非3-en-2-one，庚-3-en-2-one和5-methylhex-3-en-2-one。这些难处理的底物的对映选择性高达51％。对于环己-2-烯酮，ee达到42％。
• Investigations into the utility of high-surface area silica pellets as potential solid-phase synthesis supports
  作者：Roxana S. Timofte、Jeremy J. Titman、Limin Shao、John C. Stephens、Simon Woodward

  DOI：10.1016/j.tet.2004.10.064

  日期：2005.1

  Grace-Davidson silica pellets (SMR-057-015) are found to be optimal for surface grafting of (RO)(3)Si(CH2)(3)FG reagents. While loadings of up to 2.1 mmol g(-1) can be attained (ca. 0.05 mmol per pellet) access of further reagents to the graft sites is problematic above loadings of 0.8 mmol g(-1). C-13 CPMAS NMR studies may be carried out on individual pellets (using natural abundance substrates) and the resulting spectra are diagnostic in identifying successful subsequent coupling reactions. (C) 2004 Elsevier Ltd. All rights reserved.