2-aza-2-(1-phenylethyl)-3-ethoxycarbonyl-<2,2,2>-bicyclooct-5-ene | 869658-19-5

• 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: 2-aza-2-(1-phenylethyl)-3-ethoxycarbonyl-<2,2,2>-bicyclooct-5-ene
• 英文别名: ethyl 2-(1-phenylethyl)-2-azabicyclo[2.2.2]oct-5-ene-3-carboxylate
• CAS: 869658-19-5
• 化学式: C₁₈H₂₃NO₂
• 分子量: 285.386
• InChiKey: GFFCSDRCCRGJKW-UHFFFAOYSA-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：

  2-aza-2-(1-phenylethyl)-3-ethoxycarbonyl-<2,2,2>-bicyclooct-5-ene 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 、 铁粉 、 氯化铵 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 生成 (4-amino-2-chlorophenyl)(6,6a,7,8,9,10-hexahydro-7,10-ethanobenzo[e]pyrido[1,2-a][1,4]diazepin-5(12H)-yl)methanone
  参考文献：
  名称：

  Bridged bicyclic vasopressin receptor antagonists with V2-Selective or dual V1a/V2 activity

  摘要：

  The synthesis and biological testing of a novel series of nonpeptide vasopressin receptor antagonists, containing a bridged bicyclic nucleus, are reported. Variation of substituents (R-1-R-3) in general formula 3, and the configuration of the stereo-center, resulted in potent V-2-selective (e.g., 4) and balanced dual V-1a/V-2 (e.g., 10) compounds. Data from receptor binding, cell-based functional, and in vivo assays are presented. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00649-2
• 作为产物：
  描述：

  α-苯乙胺 在 三氟化硼乙醚 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 2-aza-2-(1-phenylethyl)-3-ethoxycarbonyl-<2,2,2>-bicyclooct-5-ene
  参考文献：
  名称：

  Bridged bicyclic vasopressin receptor antagonists with V2-Selective or dual V1a/V2 activity

  摘要：

  The synthesis and biological testing of a novel series of nonpeptide vasopressin receptor antagonists, containing a bridged bicyclic nucleus, are reported. Variation of substituents (R-1-R-3) in general formula 3, and the configuration of the stereo-center, resulted in potent V-2-selective (e.g., 4) and balanced dual V-1a/V-2 (e.g., 10) compounds. Data from receptor binding, cell-based functional, and in vivo assays are presented. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00649-2

文献信息

• 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。
• Amides as Bace Inhibitors
  申请人：Bueno Melendo Belen Ana

  公开号：US20070225372A1

  公开（公告）日：2007-09-27

  The present invention provides BRACE inhibitors of Formula (I): methods for their use, and intermediates and methods for their preparation.

  本发明提供了式（I）的BRACE抑制剂，以及其使用方法、中间体和制备方法。
• 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。
• Reaction d'aza-diels-alder diastereoselective : utilisation de la 1-phenylethyl imine de glyoxylated d'alkyle pour la synthese de derives d'α-amino acides cycliques
  作者：Hervé Abraham、Lucien Stella

  DOI：10.1016/s0040-4020(01)81187-x

  日期：1992.1

  The use of trifluoroacetic acid-boron trifluoride combination is highly effective in dichloromethane for the activation of 1-phenylethylimine of methyl or ethyl glyoxylates as heterodienophiles in Diels-Alder cycloaddition reactions with a series of conjugated dienes. High regio-(meta:para) and stereo-(endo:exo) selectivities are observed at low temperature. Asymmetric induction is very high (>98%) with cyclopentadiene but remains low in the other cases.
• 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