(S)-(-)-diphenylvalinol | 219638-89-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-(-)-diphenylvalinol
• 英文别名: (S)-N,N-diphenylvalinol；(s)-Diphenyl valinol；(2S)-3-methyl-2-(N-phenylanilino)butan-1-ol
• CAS: 219638-89-8
• 化学式: C₁₇H₂₁NO
• 分子量: 255.36
• InChiKey: KFEQLVLEDQJHGP-QGZVFWFLSA-N

物化性质

• 沸点：
  392.6±25.0 °C(Predicted)
• 密度：
  1.071±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(-)-diphenylvalinol 在 三乙胺 、 丁酮 作用下， 以 二氯甲烷 为溶剂， 反应 12.5h， 生成 ((S)-3-Methyl-2-thiocyanato-butyl)-diphenyl-amine
  参考文献：
  名称：

  Concepts for ligand design in asymmetric catalysis: a study of chiral amino thiol ligands

  摘要：

  A series of new chiral sulfur-nitrogen chelate ligands, derived from amino acids, has been synthesised rationally. Fruitless experiments into catalytic asymmetric conjugate additions and desymmetrisation of meso-epoxides led us to analyse our ligands in the catalytic asymmetric addition of diethylzinc to aromatic aldehydes. These latter experiments were successful with chiral benzylic alcohols being obtained in up to 82% enantiomeric excess. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00344-9
• 作为产物：
  描述：

  triphenylbismuth(V) diacetate 在 lithium aluminium tetrahydride 、 copper diacetate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 361.0h， 生成 (S)-(-)-diphenylvalinol
  参考文献：
  名称：

  The importance of nitrogen substituents in chiral amino thiol ligands for the asymmetric addition of diethylzinc to aromatic aldehydes

  摘要：

  一系列源自（S）-缬氨酸的N,S-螯合配体具有立体中心氮供体原子的特性，作为催化剂用于二乙基锌与芳香醛的加成反应，产物次级醇的对映体过量可达82%。

  DOI：

  10.1039/a707937k
• 作为试剂：
  描述：

  (E)-4-methoxyacetophenone oxime 2-nitrobenzyl ether 在 (S)-(-)-diphenylvalinol 、 diborane(6) 作用下， 以75%的产率得到(S)-(-)-1-(4-甲氧基苯)乙胺
  参考文献：
  名称：

  Laczkowski, Krzysztof Z., Acta poloniae pharmaceutica, 2013, vol. 70, # 2, p. 237 - 244

  摘要：

  DOI：

文献信息

• The importance of nitrogen substituents in chiral amino thiol ligands for the asymmetric addition of diethylzinc to aromatic aldehydes
  作者：James C. Anderson

  DOI：10.1039/a707937k

  日期：——

  A new series of N,S-chelate ligands derived from (S)-valine, which possess the capability of a stereogenic nitrogen donor atom, are catalysts for the addition of diethylzinc to aromatic aldehydes and gave the product secondary alcohols in up to 82% ee.

  一系列源自（S）-缬氨酸的N,S-螯合配体具有立体中心氮供体原子的特性，作为催化剂用于二乙基锌与芳香醛的加成反应，产物次级醇的对映体过量可达82%。
• Dramatic reversal of enantioselection in a palladium catalysed allylic substitution by choice of nitrogen substituents in a N–P chiral ligand
  作者：James C. Anderson、Rachel J. Cubbon、John D. Harling

  DOI：10.1016/s0957-4166(99)00298-0

  日期：1999.7

  Two chiral chelate nitrogen–phosphorus ligands derived from (S)-valine, with the potential for stereogenic nitrogen donors, gave dramatically different enantioselectivities, ranging from 92% ee (R) to 83% ee (S), in the palladium catalysed allylic substitution reaction.

  衍生自（S）-缬氨酸的两个手性螯合氮-磷配体具有立体生成氮供体的潜力，在钯催化的烯丙基取代反应中，对映选择性大大不同，从92％ee（R）到83％ee（S）反应。
• [EN] CATALYTIC ASYMMETRIC SYNTHESIS OF PRIMARY AMINES VIA BORANE REDUCTION OF OXIME ETHERS USING SPIROBORATE ESTERS<br/>[FR] SYNTHÈSE ASYMÉTRIQUE CATALYTIQUE D'AMINES PRIMAIRES PAR RÉDUCTION AU BORANE D'ÉTHERS D'OXIME AU MOYEN D'ESTERS DE SPIROBORATE
  申请人：INTELLECTUAL PROPERTY AND TECH

  公开号：WO2008027740A3

  公开（公告）日：2008-05-22
• Investigation of the importance of nitrogen substituents in a N–P chiral ligand for enantioselective allylic alkylation
  作者：James C. Anderson、Rachel J. Cubbon、John D. Harling

  DOI：10.1016/s0957-4166(01)00137-9

  日期：2001.4

  The synthesis of three chiral chelate nitrogen-phosphorus (S)-valine derived ligands with the potential fur stereogenic nitrogen donation is described. In palladium catalysed allylic substitution reactions the ligands induced varying enantioselectivities ranging From 92%, e.e. of the (R)-enantiomer to 83% e.e. of the (S)-enantiomer. Structural and spectroscopic investigations into the origin of this effect were conducted, but were inconclusive. However, the importance of the consideration of N-substituents in such systems is highlighted. (C) 2001 Elsevier Science Ltd. All rights reserved.
• EP1981831A2
  申请人：——

  公开号：EP1981831A2

  公开（公告）日：2008-10-22