Methanesulfonic acid (S)-2-diphenylamino-3-methyl-butyl ester | 251087-95-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: Methanesulfonic acid (S)-2-diphenylamino-3-methyl-butyl ester
• CAS: 251087-95-3
• 化学式: C₁₈H₂₃NO₃S
• 分子量: 333.452
• InChiKey: MYZUWRGWUUTGPK-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (S)-2-diphenylamino-3-methyl-butyl ester 在 lithium aluminium tetrahydride 、 氧气 、 丁酮 作用下， 反应 12.5h， 生成 (S,S)-bis-(N,N-diphenyl-1-amino-3-methylbutane-2-)disulfide
  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 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 361.0h， 生成 Methanesulfonic acid (S)-2-diphenylamino-3-methyl-butyl ester
  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

文献信息

• 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。
• 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.
• Concepts for ligand design in asymmetric catalysis: a study of chiral amino thiol ligands
  作者：James C. Anderson、Rachel Cubbon、Michael Harding、Daniel S. James

  DOI：10.1016/s0957-4166(98)00344-9

  日期：1998.10

  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.