(R)-(1-naphthyl)glycyl-(R)-phenylglycine | 160289-70-3

• 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: (R)-(1-naphthyl)glycyl-(R)-phenylglycine
• 英文别名: (2R)-{[(2R)-2-Amino-2-(naphthalen-1-yl)acetyl]amino}(phenyl)acetic acid；(2R)-2-[[(2R)-2-amino-2-naphthalen-1-ylacetyl]amino]-2-phenylacetic acid
• CAS: 160289-70-3
• 化学式: C₂₀H₁₈N₂O₃
• 分子量: 334.375
• InChiKey: GIZWTILBXBCNDE-QZTJIDSGSA-N

物化性质

• 沸点：
  635.0±55.0 °C(Predicted)
• 密度：
  1.307±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-扁桃酸甲酯 、 (R)-(1-naphthyl)glycyl-(R)-phenylglycine 以 甲醇 为溶剂， 以47%的产率得到
  参考文献：
  名称：

  Enantiomeric Inclusion of α-Hydroxy Esters by (R)-(1-Naphthyl)glycyl-(R)-phenylglycine and the Crystal Structures of the Inclusion Cavities

  摘要：

  A simple dipeptide, (R)-(l-naphthyl)glycyl-(R)-phenylglycine [(R,R)-1], formed inclusion compounds with several alpha-hydroxy esters (2) with high enantioselectivity. By crystallization of a mixture of the dipeptide [(R,R)-1] and racemic 2a [MeCH(OH)COOMe] from methanol, asymmetric recognition occurred to give an inclusion compound that contains the S form of 2a in 89% ee: X-ray crystallographic study of the inclusion compound elucidated that the dipeptide molecules arrange in a "folded antiparallel" beta-sheetlike structure to accommodate the alpha-hydroxy ester in the pocket-type cavity surrounded by naphthyl and phenyl groups on the sheet. Similarly, 2b [MeCH(OH)COOEt] and 2f [dihydro-3-hydroxy-4,4-dimethyl-2(3H)-furanone] were included with high enantioselectivity of the S form. When bulkier 2l [t-BuCH(OH)COOMe] was used as a guest molecule, the arrangement of dipeptide molecules changed to an "extended antiparallel" mode, where the naphthyl and phenyl groups arranged in a "parallel stacked and displaced" mode and a channel-type cavity was constructed. The guest molecules were accommodated via hydrogen bonding in the channel-type cavity with high enantioselectivity of the S form (82% ee). In the case of 2k [i-PrCH(OH)COOMe], optically pure (S)-2k formed the dipeptide sheet with the "folded antiparallel" structure by cocrystallization with (R,R)-1, while the "extended antiparallel" structure appeared in the inclusion of racemic 2k.

  DOI：

  10.1021/jo9818778
• 作为产物：
  描述：

  (R)-氨基萘-1-乙酸 在 钯 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 生成 (R)-(1-naphthyl)glycyl-(R)-phenylglycine
  参考文献：
  名称：

  结晶(R)-芳基甘氨酰基-(R)-苯基甘氨酸对1,2-二甲氧基苯衍生物的特异性包合及其结构

  摘要：

  (R)-芳基甘氨酰-(R)-苯基甘氨酸（1，芳基=苯基；2，芳基=1-萘基）在1,2-二甲氧基苯或其衍生物存在下的结晶得到包含化合物。单晶 X 射线分析表明，在 1,2-二甲氧基苯包合物中，二肽分子排列成片状，而 1,2-二甲氧基苯通过锚定在片状体之间的空隙中而位于末端片材上的氨氢通过三中心氢键。发现片材之间的距离根据客体 1,2-二甲氧基苯衍生物的长度而变化，就好像它们是支撑片材的柱子一样。

  DOI：

  10.1246/bcsj.70.2823

文献信息

• Enantiomeric Inclusion of α-Hydroxy Esters by (<i>R</i>)-(1-Naphthyl)glycyl-(<i>R</i>)-phenylglycine and the Crystal Structures of the Inclusion Cavities
  作者：Motohiro Akazome、Toshiaki Takahashi、Katsuyuki Ogura

  DOI：10.1021/jo9818778

  日期：1999.4.1

  A simple dipeptide, (R)-(l-naphthyl)glycyl-(R)-phenylglycine [(R,R)-1], formed inclusion compounds with several alpha-hydroxy esters (2) with high enantioselectivity. By crystallization of a mixture of the dipeptide [(R,R)-1] and racemic 2a [MeCH(OH)COOMe] from methanol, asymmetric recognition occurred to give an inclusion compound that contains the S form of 2a in 89% ee: X-ray crystallographic study of the inclusion compound elucidated that the dipeptide molecules arrange in a "folded antiparallel" beta-sheetlike structure to accommodate the alpha-hydroxy ester in the pocket-type cavity surrounded by naphthyl and phenyl groups on the sheet. Similarly, 2b [MeCH(OH)COOEt] and 2f [dihydro-3-hydroxy-4,4-dimethyl-2(3H)-furanone] were included with high enantioselectivity of the S form. When bulkier 2l [t-BuCH(OH)COOMe] was used as a guest molecule, the arrangement of dipeptide molecules changed to an "extended antiparallel" mode, where the naphthyl and phenyl groups arranged in a "parallel stacked and displaced" mode and a channel-type cavity was constructed. The guest molecules were accommodated via hydrogen bonding in the channel-type cavity with high enantioselectivity of the S form (82% ee). In the case of 2k [i-PrCH(OH)COOMe], optically pure (S)-2k formed the dipeptide sheet with the "folded antiparallel" structure by cocrystallization with (R,R)-1, while the "extended antiparallel" structure appeared in the inclusion of racemic 2k.
• Specific Inclusion of 1,2-Dimethoxybenzene Derivatives by Crystalline (<i>R</i>)-Arylglycyl-(<i>R</i>)-phenylglycines and Its Structure
  作者：Motohiro Akazome、Yukiko Yanagita、Ryo-ichi Sonobe、Katsuyuki Ogura

  DOI：10.1246/bcsj.70.2823

  日期：1997.11

  The crystallization of (R)-arylglycyl-(R)-phenylglycine (1, aryl = phenyl; 2, aryl = 1-naphthyl) in the presence of 1,2-dimethoxybenzene or its derivatives affords an inclusion compound. A single-crystal X-ray analysis has shown that, in a 1,2-dimethyoxybenzene inclusion compound, dipeptide molecules arrange in a sheet and the 1,2-dimethoxybenzene lies at the end in a void between the sheets by being

  (R)-芳基甘氨酰-(R)-苯基甘氨酸（1，芳基=苯基；2，芳基=1-萘基）在1,2-二甲氧基苯或其衍生物存在下的结晶得到包含化合物。单晶 X 射线分析表明，在 1,2-二甲氧基苯包合物中，二肽分子排列成片状，而 1,2-二甲氧基苯通过锚定在片状体之间的空隙中而位于末端片材上的氨氢通过三中心氢键。发现片材之间的距离根据客体 1,2-二甲氧基苯衍生物的长度而变化，就好像它们是支撑片材的柱子一样。