[(2S)-1-[(2-benzhydryl-4-oxoquinazolin-3-yl)-(2-methylpropanoyl)amino]-1-oxopropan-2-yl] acetate | 156904-85-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2S)-1-[(2-benzhydryl-4-oxoquinazolin-3-yl)-(2-methylpropanoyl)amino]-1-oxopropan-2-yl] acetate
• CAS: 156904-85-7
• 化学式: C₃₀H₂₉N₃O₅
• 分子量: 511.577
• InChiKey: SGLPDYRMBFPPMP-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  96.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  α-苯乙胺 、 [(2S)-1-[(2-benzhydryl-4-oxoquinazolin-3-yl)-(2-methylpropanoyl)amino]-1-oxopropan-2-yl] acetate 以 甲苯 为溶剂， 生成 Acetic acid (S)-1-(1-phenyl-ethylcarbamoyl)-ethyl ester
  参考文献：
  名称：

  The N–N bond as a chiral axis: 3-(diacylamino)quinazolin-4(3H)ones as chiral acylating agents

  摘要：

  通过晶体结构测定，确认了 NâN 手性轴的存在，从而分离并识别出 3-（二酰氨基）喹唑啉酮 5 的两种非对映异构体：其中一种非对映异构体 8 与外消旋 1-苯基乙胺反应，只在 2-乙酰氧基丙酰亚胺羰基上发生反应，并通过动力学解析得到非对映异构体 10，比例为 3.6:1。

  DOI：

  10.1039/c39940001159
• 作为产物：
  描述：

  2-过氧乙酰丙酰氯 在 吡啶 作用下， 生成 [(2S)-1-[(2-benzhydryl-4-oxoquinazolin-3-yl)-(2-methylpropanoyl)amino]-1-oxopropan-2-yl] acetate
  参考文献：
  名称：

  The N–N bond as a chiral axis: 3-(diacylamino)quinazolin-4(3H)ones as chiral acylating agents

  摘要：

  通过晶体结构测定，确认了 NâN 手性轴的存在，从而分离并识别出 3-（二酰氨基）喹唑啉酮 5 的两种非对映异构体：其中一种非对映异构体 8 与外消旋 1-苯基乙胺反应，只在 2-乙酰氧基丙酰亚胺羰基上发生反应，并通过动力学解析得到非对映异构体 10，比例为 3.6:1。

  DOI：

  10.1039/c39940001159

文献信息

• The N–N bond as a chiral axis: 3-diacylaminoquinazolinones as chiral acylating agents
  作者：Robert S. Atkinson、Emma Barker、Paul J. Edwards、Gordon A. Thomson

  DOI：10.1039/p19960001047

  日期：——

  3-Diacylaminoquinazolinones 10 and 15 have high enough barriers to rotation around their N-N bonds to allow separation of each into diastereoisomers. Interconversion of diastereoisomers 10a and 10b occurs on heating in boiling toluene and thermodynamic parameters for this process have been measured, The barriers to rotation around the N-N bonds in analogous monoacylaminoquinazolinones are not sufficient to permit isolation of stereoisomers at room temperature unless the exocyclic nitrogen is additionally substituted e.g. by an alkyl group as in 28, X-Ray crystal structure determinations carried out on 10a, 10b, 15a and 28b confirm the presence of chiral axes, Reaction of both diastereoisomers 15a and 15b with 1-phenylethylamine takes place with exclusive reaction at the 1-acetoxypropionyl carbonyl group and with partial kinetic resolution: the preferred sense of enantioselectivity obtained is dominated by the N-N axis.
• 3-Di-[(S)-2-acetoxypropanoyl]aminoquinazolin-4(3H)-ones: stereostructure and application in kinetic resolution of amines
  作者：Abdullah G Al-Sehemi、Robert S Atkinson、John Fawcett、David R Russell

  DOI：10.1016/s0040-4039(00)00139-8

  日期：2000.3

  Whereas 3-diacylaminoquinazolin-4(3H)-ones (DAQs) have been previously shown to undergo rapid exo/endo-endo/exo conformational interconversion of their imide carbonyl groups, the title DAQs are believed to exist in one single exo/endo form and consequently their N-N bonds are chiral axis: one of these DAQs, substituted with a diphenylmethyl group on the Q-2 position, reacts preferentially with one enantiomer of racemic 2-methyl-piperidine at the 2-acetoxypropanoyl imide carbonyl group (ee 94%). (C) 2000 Elsevier Science Ltd. All rights reserved.
• The N–N bond as a chiral axis: 3-(diacylamino)quinazolin-4(3H)ones as chiral acylating agents
  作者：Robert S. Atkinson、Emma Barker、Christopher J. Price、David R. Russell

  DOI：10.1039/c39940001159

  日期：——

  Two diasteroisomers of 3-(diacylamino)quinazolinone 5 are separated and identified by crystal structure determinations which confirm the presence of an N–N chiral axis: one diastereoisomer of enantiopure 8 reacts with racemic 1-phenylethylamine exclusively at the 2-acetoxypropanoyl imide carbonyl group and with kinetic resolution to give a 3.6 : 1 ratio of diastereoisomers of 10.

  通过晶体结构测定，确认了 NâN 手性轴的存在，从而分离并识别出 3-（二酰氨基）喹唑啉酮 5 的两种非对映异构体：其中一种非对映异构体 8 与外消旋 1-苯基乙胺反应，只在 2-乙酰氧基丙酰亚胺羰基上发生反应，并通过动力学解析得到非对映异构体 10，比例为 3.6:1。