(R)-1,3,3',4'-tetrahydro-2'H-spiro[indene-2,1'-naphthalen]-2'-ol | 1315589-73-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (R)-1,3,3',4'-tetrahydro-2'H-spiro[indene-2,1'-naphthalen]-2'-ol
• 英文别名: SRC 549；(2'R)-spiro[1,3-dihydroindene-2,1'-3,4-dihydro-2H-naphthalene]-2'-ol
• CAS: 1315589-73-1
• 化学式: C₁₈H₁₈O
• 分子量: 250.34
• InChiKey: CYGIQGSISIZZLR-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-1,3,3',4'-tetrahydro-2'H-spiro[indene-2,1'-naphthalen]-2'-ol 、 右旋樟脑-10-磺酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以64%的产率得到SRC 553
  参考文献：
  名称：

  An Unexpected Directing Effect in the Asymmetric Transfer Hydrogenation of α,α-Disubstituted Ketones

  摘要：

  alpha,alpha-Disubstituted ketones containing an aromatic ring or alkene are reduced in high enantiomeric excess using an asymmetric transfer hydrogenation catalyst. The sense of reduction indicates that the unsaturated region of the ketone adopts a position adjacent to the Ru-bound eta(6)-arene ring in the reduction transition state.

  DOI：

  10.1021/ol201643v
• 作为产物：
  描述：

  β-四氢萘酮 在 甲酸 、 N-[(1R,2R)-1,2-diphenyl-2-(3-phenylpropylamino)ethyl]-4-methylbenzene sulfonamide ammonium chloride ruthenium 、 四丁基溴化铵 、 三乙胺 、 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 28.0h， 生成 (R)-1,3,3',4'-tetrahydro-2'H-spiro[indene-2,1'-naphthalen]-2'-ol
  参考文献：
  名称：

  An Unexpected Directing Effect in the Asymmetric Transfer Hydrogenation of α,α-Disubstituted Ketones

  摘要：

  alpha,alpha-Disubstituted ketones containing an aromatic ring or alkene are reduced in high enantiomeric excess using an asymmetric transfer hydrogenation catalyst. The sense of reduction indicates that the unsaturated region of the ketone adopts a position adjacent to the Ru-bound eta(6)-arene ring in the reduction transition state.

  DOI：

  10.1021/ol201643v

文献信息

• Kinetic Resolution of Neopentylic Secondary Alcohols by Cu–H-Catalyzed Enantioselective Silylation with Hydrosilanes
  作者：Zaneta Papadopulu、Martin Oestreich

  DOI：10.1021/acs.orglett.0c03943

  日期：2021.1.15

  A nonenzymatic kinetic resolution of sterically congested alcohols having a quaternary carbon atom in the β-position is reported. The catalyst system CuCl/NaOtBu/(R,R)-Ph-BPE together with a 3,5-xylyl-substituted tertiary hydrosilane enable enantioselective silylation of the hydroxy group. Several alcohols are obtained with good to excellent selectivity factors, and there are no other known straightforward

  报道了在β位具有季碳原子的空间拥挤的醇的非酶动力学拆分。催化剂体系CuCl / NaO t Bu /（R，R）-Ph-BPE与3,5-二甲苯基取代的叔氢硅烷一起使羟基的对映选择性硅烷化成为可能。获得了具有良好至优异的选择性因子的几种醇，并且没有其他已知的直接方法可访问这些基序。
• An Unexpected Directing Effect in the Asymmetric Transfer Hydrogenation of α,α-Disubstituted Ketones
  作者：Rina Soni、John-Michael Collinson、Guy C. Clarkson、Martin Wills

  DOI：10.1021/ol201643v

  日期：2011.8.19

  alpha,alpha-Disubstituted ketones containing an aromatic ring or alkene are reduced in high enantiomeric excess using an asymmetric transfer hydrogenation catalyst. The sense of reduction indicates that the unsaturated region of the ketone adopts a position adjacent to the Ru-bound eta(6)-arene ring in the reduction transition state.