(1R,3R,4S)-2-<(1S)-phenylethyl>-2-aza-bicyclo<2.2.2>oct-5-ene-3-carboxylic acid ethyl ester | 210645-26-4

• 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: (1R,3R,4S)-2-<(1S)-phenylethyl>-2-aza-bicyclo<2.2.2>oct-5-ene-3-carboxylic acid ethyl ester
• 英文别名: ethyl (1R, 3R, 4S)-2-[(S)-1-phenylethyl]-2-azabicyclo[2.2.2]oct-5-ene-3-carboxylate；(1R,3R,4S)-Ethyl 2-((S)-1-phenylethyl)-2-azabicyclo[2.2.2]oct-5-ene-3-carboxylate；ethyl (1R,3R,4S)-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.2]oct-5-ene-3-carboxylate
• CAS: 210645-26-4
• 化学式: C₁₈H₂₃NO₂
• 分子量: 285.386
• InChiKey: GFFCSDRCCRGJKW-PQEBFOHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,3R,4S)-2-<(1S)-phenylethyl>-2-aza-bicyclo<2.2.2>oct-5-ene-3-carboxylic acid ethyl ester 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以93%的产率得到(2R)-cyclohexyl glycine ethyl ester
  参考文献：
  名称：

  New Expedient Route to Both Enantiomers of Nonproteinogenic α-Amino Acid Derivatives from the Unsaturated 2-Aza-Bicyclo Moiety

  摘要：

  The influence of the reaction conditions on the catalytic hydrogenation of 2-aza-bicyclo hept-5-ene and oct-5-ene derivatives has been investigated. We found it possible to fully control the extent of allylic vs benzylic C-N hydrogenolysis by simple variations of H-2 pressure and acidity of the reaction medium. The use of the reaction pathways was demonstrated by the selective preparation of four categories of optically active alpha-amino acid derivatives. The strategy was also extended to the synthesis of enantiopure alpha-amino ketones.

  DOI：

  10.1021/jo981838w
• 作为产物：
  描述：

  ethyl <(S)-1-phenylethyl>iminoethanoate 、 1,3-环己二烯 生成 (1R,3R,4S)-2-<(1S)-phenylethyl>-2-aza-bicyclo<2.2.2>oct-5-ene-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Chiral sulfonamides with various N-heterocyclic and aromatic units – Synthesis and antiviral activity evaluation

  摘要：

  DOI：

  10.1016/j.biopha.2022.113473

文献信息

• 2-Azanorbornyl Alcohols:  Very Efficient Ligands for Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation of Aromatic Ketones
  作者：Diego A. Alonso、Sofia J. M. Nordin、Peter Roth、Tibor Tarnai、Pher G. Andersson、Marc Thommen、Ulrich Pittelkow

  DOI：10.1021/jo991914a

  日期：2000.5.1

  2-Azanorbornyl-derived amino alcohols were prepared and evaluated as ligands in the Ru(II)-catalyzed asymmetric transfer hydrogenation of aromatic ketones. To improve selectivity and rate, the structure of the ligand was optimized. Acetophenone was reduced using 0.5 mol % catalyst in 40 min in 94% ee. This system was also able to reduce a wide range of aromatic ketones to the corresponding alcohols, while maintaining

  制备了2-氮杂降冰片基衍生的氨基醇，并将其评估为Ru（II）催化的芳族酮的不对称转移氢化中的配体。为了提高选择性和速率，对配体的结构进行了优化。在40分钟内于94％ee中，使用0.5 mol％的催化剂还原苯乙酮。该体系还能够将多种芳族酮还原为相应的醇，同时保持高对映选择性和产率。检查了催化剂负载和反应容器中助溶剂存在的影响，并进行了线性研究。
• Azabicyclo compound matrix metalloprotease inibitor and skin preparation
  申请人：Hiruma Takuya

  公开号：US20050009808A1

  公开（公告）日：2005-01-13

  An azabicyclo compound (I) or a salt thereof in accordance with the present invention has an excellent inhibiting action on matrix metalloproteases (MMPs) activity, and is useful for pharmaceutical, cosmetic and skin external compositions. wherein R is H, alkyl, heteroalkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, acyl, COOR 1 , carbamoyl or SO 2 R 2 (wherein R 1 and R 2 each are alkyl, heteroalkyl, aryl, heteroaryl, arylalkyl or heteroarylalkyl); X is methylene, ethylene or propylene; and is a single bond or a double bond.

  本发明提供的一种氮杂双环化合物(I)或其盐在抑制基质金属蛋白酶(MMPs)活性方面具有优异的作用，并可用于制药、化妆品和皮肤外用组合物中。其中R为H、烷基、杂基烷基、芳基、杂芳基、芳基烷基、杂芳基烷基、酰基、COOR1、氨基甲酰或SO2R2（其中R1和R2各自为烷基、杂基烷基、芳基、杂芳基、芳基烷基或杂芳基烷基）；X为亚甲基、乙烯基或丙烯基；而表示单键或双键。
• Azabicyclo compound matrix metalloprotease inhibitor and skin preparation
  申请人：Shiseido Co., Ltd.

  公开号：US07176217B2

  公开（公告）日：2007-02-13

  An azabicyclo compound (I) or a salt thereof in accordance with the present invention has an excellent inhibiting action on matrix metalloproteases (MMPs) activity, and is useful for pharmaceutical, cosmetic and skin external compositions. wherein R is H, alkyl, heteroalkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, acyl, COOR1, carbamoyl or SO2R2 (wherein R1 and R2 each are alkyl, heteroalkyl, aryl, heteroaryl, arylalkyl or heteroarylalkyl); X is methylene, ethylene or propylene; and is a single bond or a double bond.

  本发明所述的一种azabicyclo化合物（I）或其盐对基质金属蛋白酶（MMPs）活性具有优异的抑制作用，可用于制药、化妆品和皮肤外用组合物中。其中R为H、烷基、杂烷基、芳基、杂芳基、芳基烷基、杂芳基烷基、酰基、COOR1、氨基甲酰或SO2R2（其中R1和R2各自为烷基、杂烷基、芳基、杂芳基、芳基烷基或杂芳基烷基）；X为亚甲基、乙烯基或丙烯基；且为单键或双键。
• (1S, 3R, 4R)-2-Azanorbornyl-3-methanol oxazaborolidines in the asymmetric reduction of ketones
  作者：Pedro Pinho、David Guijarro、Pher G. Andersson

  DOI：10.1016/s0040-4020(98)00424-4

  日期：1998.7

  Synthesis of new rigid (1S, 3R, 4R)-2-azanorbornyl-3-methanols and its application in the asymmetric borane reduction of ketones are described. The influence of temperature, solvent and concentration on the reaction outcome were also studied and enantiomeric excess up to 89% could be obtained. (C) 1998 Elsevier Science Ltd. All rights reserved.
• AZABICYCLO COMPOUND, MATRIX METALLOPROTEASE INHIBITOR, AND SKIN PREPARATION
  申请人：Shiseido Co., Ltd.

  公开号：EP1452527B1

  公开（公告）日：2009-03-04