(3R,7aS)-2-butyl-3-naphthalen-1-yl-5,6,7,7a-tetrahydro-3H-pyrrolo[1,2-c]imidazol-1-one | 1526931-26-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (3R,7aS)-2-butyl-3-naphthalen-1-yl-5,6,7,7a-tetrahydro-3H-pyrrolo[1,2-c]imidazol-1-one
• CAS: 1526931-26-9
• 化学式: C₂₀H₂₄N₂O
• 分子量: 308.423
• InChiKey: KCWFBGZTBODIOV-RBUKOAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,7aS)-2-butyl-3-naphthalen-1-yl-5,6,7,7a-tetrahydro-3H-pyrrolo[1,2-c]imidazol-1-one 在 盐酸羟胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 、 甲苯 为溶剂， 反应 1.17h， 生成
  参考文献：
  名称：

  An analysis of the complementary stereoselective alkylations of imidazolidinone derivatives toward α-quaternary proline-based amino amides

  摘要：

  Alkylations of praline-based imidazolidinones are described based on the principle of self-regeneration of stereocenters (SRS), affording high levels of either the cis or trans configured products. Stereoselectivity is dictated solely on the nature of the 'temporary' group, where isobutyraldehyde-derived imidazolidinones provide the cis configured products and 1-naphthaldehyde-derived imidazolidinones afford the complementary trans configured products. These stereodivergent products can be readily cleaved to afford both alpha-alkylated proline enantiomers from readily available L-proline. A series of imidazolidinones were alkylated to investigate the origin of the anti-selectivity. Potential contributions toward the observed anti-selectivity are discussed on the basis of these experiments, suggesting a refined hypothesis for selectivity may be in order. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.010
• 作为产物：
  描述：

  L-脯氨酸 在 盐酸 、 potassium carbonate 、 三乙胺 、 sodium hydroxide 、 氯甲酸异丁酯 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 乙二醇 为溶剂， 反应 25.5h， 生成 (3R,7aS)-2-butyl-3-naphthalen-1-yl-5,6,7,7a-tetrahydro-3H-pyrrolo[1,2-c]imidazol-1-one
  参考文献：
  名称：

  Complementary Stereochemical Outcomes in Proline-Based Self-Regenerations of Stereocenters

  摘要：

  Stereoselective alkylations of proline-based amino amides are described, where high levels of either a cis or trans configuration can be attained simply by the choice of the aminal group. Isobutryaldehyde-derived aminals provide the cis configuration, while 1-naphthaldehyde-derived aminals engender the complementary trans configuration.

  DOI：

  10.1021/ol403320d

文献信息

• An analysis of the complementary stereoselective alkylations of imidazolidinone derivatives toward α-quaternary proline-based amino amides
  作者：Brian J. Knight、Erin E. Stache、Eric M. Ferreira

  DOI：10.1016/j.tet.2015.05.010

  日期：2015.9

  Alkylations of praline-based imidazolidinones are described based on the principle of self-regeneration of stereocenters (SRS), affording high levels of either the cis or trans configured products. Stereoselectivity is dictated solely on the nature of the 'temporary' group, where isobutyraldehyde-derived imidazolidinones provide the cis configured products and 1-naphthaldehyde-derived imidazolidinones afford the complementary trans configured products. These stereodivergent products can be readily cleaved to afford both alpha-alkylated proline enantiomers from readily available L-proline. A series of imidazolidinones were alkylated to investigate the origin of the anti-selectivity. Potential contributions toward the observed anti-selectivity are discussed on the basis of these experiments, suggesting a refined hypothesis for selectivity may be in order. (C) 2015 Elsevier Ltd. All rights reserved.
• Complementary Stereochemical Outcomes in Proline-Based Self-Regenerations of Stereocenters
  作者：Brian J. Knight、Erin E. Stache、Eric M. Ferreira

  DOI：10.1021/ol403320d

  日期：2014.1.17

  Stereoselective alkylations of proline-based amino amides are described, where high levels of either a cis or trans configuration can be attained simply by the choice of the aminal group. Isobutryaldehyde-derived aminals provide the cis configuration, while 1-naphthaldehyde-derived aminals engender the complementary trans configuration.