(S)-2-(N,N-dibenzylamino)-2-phenylacetic acid (R)-pantolactone ester | 151302-17-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-(N,N-dibenzylamino)-2-phenylacetic acid (R)-pantolactone ester
• 英文别名: (R)-O-[(2-bisphenylmethylamino)-2-phenyl]acetylpantolactone；[(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (2S)-2-(dibenzylamino)-2-phenylacetate
• CAS: 151302-17-9
• 化学式: C₂₈H₂₉NO₄
• 分子量: 443.543
• InChiKey: ZUXVWMDUDNKDJA-DQEYMECFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-(N,N-dibenzylamino)-2-phenylacetic acid (R)-pantolactone ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.5h， 以89%的产率得到(S)-2-(N,N-dibenzylamino)-2-phenylethanol
  参考文献：
  名称：

  Enantioselective Synthesis of β-Dibenzylamino Alcohols via a Dynamic Kinetic Resolution of α-Halo Acids

  摘要：

  DOI：

  10.1021/jo9712714
• 作为产物：
  描述：

  D-(-)-泛酰内酯 在 4-二甲氨基吡啶 、 四丁基碘化铵 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (S)-2-(N,N-dibenzylamino)-2-phenylacetic acid (R)-pantolactone ester
  参考文献：
  名称：

  Enantioselective Synthesis of β-Dibenzylamino Alcohols via a Dynamic Kinetic Resolution of α-Halo Acids

  摘要：

  DOI：

  10.1021/jo9712714

文献信息

• Reaction of (R)-pantolactone esters of alpha-bromoacids with amines a remarkable synthesis of optically active alpha-amino esters
  作者：Kevin Koh、Robert N. Ben、Tony Durst

  DOI：10.1016/0040-4039(93)88062-n

  日期：1993.7

  (R)-Pantolactone esters of racemic α-bromo acids react with amines to give α-amino esters having the (S)-configuration at the α-carbon in yields which are considerably greater than the 50% expected on the basis of a simple SN2 displacement reaction.

  外消旋α-溴酸的（R）-内酯酯与胺反应生成α-碳上具有（S）-构型的α-氨基酯，其收率大大高于简单估算的50％预期S N 2置换反应。
• Synthesis of Optically Active α-Amino Esters via Dynamic Kinetic Resolution:  A Mechanistic Study
  作者：Robert N. Ben、Tony Durst

  DOI：10.1021/jo9811625

  日期：1999.10.1

  Synthesis of N-protected optically active alpha-amino esters from racemic alpha-halo esters via dynamic kinetic resolution (DKR) mill be described. This methodology is general in nature and provides the desired optically active N-protected amino esters in 70-95% yield with diastereomeric excesses in the range of 85 to >98%. Applications and mechanistic aspects mill be discussed.
• Asymmetric Preparation of New N,N-Dialkyl-2-amino-1,1,2-triphenylethanol Catalysts and a Kinetic Resolution in the Addition of Diethylzinc to Flavene-3-carbaldehydes
  作者：Yong Park、Seock Kang、Jinho Baek、Yi Ko、Chan Im

  DOI：10.1055/s-0032-1318301

  日期：——

  Enantiopure N,N-dialkyl-(S)-2-amino-1,1,2-triphenylethanols were prepared using a new synthetic methodology and tested for their ability to catalyze the enantioselective addition of diethylzinc to aldehydes. The structural modification of N- substituents of the catalysts led us to identify N- methyl- N-(S)-1-phenylethyl-substituted 4d as an effective catalyst for the addition. Also disclosed is a kinetic resolution of racemic flavene-3-carbaldehydes with the chiral catalyst.
• Enantioselective Synthesis of β-Dibenzylamino Alcohols via a Dynamic Kinetic Resolution of α-Halo Acids
  作者：Jeff A. O'Meara、Nizar Gardee、Manfred Jung、Robert N. Ben、Tony Durst

  DOI：10.1021/jo9712714

  日期：1998.5.1