nopinylamine | 64284-82-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: nopinylamine
• 英文别名: (1R,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-amine
• CAS: 64284-82-8
• 化学式: C₉H₁₇N
• 分子量: 139.241
• InChiKey: VFQYFRUGGATHGJ-BIIVOSGPSA-N

物化性质

• 沸点：
  179℃
• 密度：
  0.920
• 闪点：
  48℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  nopinylamine 在 ammonium hydroxide 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 17.5h， 生成 [(3-Acetylsulfanyl-2-methyl-propionyl)-((1S,2S,5R)-6,6-dimethyl-bicyclo[3.1.1]hept-2-yl)-amino]-acetic acid
  参考文献：
  名称：

  Angiotensin-converting enzyme inhibitors. New orally active antihypertensive (mercaptoalkanoyl)- and [(acylthio)alkanoyl]glycine derivatives

  摘要：

  A variety of N-substituted (mercaptoalkanoyl)- and [(acylthio)alkanoyl]glycine derivatives was synthesized and their ability in inhibiting the activity of angiotensin-converting enzyme (ACE) was examined in vitro and in vivo. The acylthio derivatives prepared are assumed to act as prodrugs since they are much less active than the corresponding free SH compounds in vitro and can be expected to act in vivo only after conversion to the free sulfhydryl compounds. A number of these compounds are potent ACE inhibitors that lowered blood pressure in Na-deficient, conscious spontaneously hypertensive rats (SHR), a high renin model. One of the most active members of the series was (S)-N-cyclopentyl-N-[3-[(2,2-dimethyl-1-oxopropyl)thio]-2-methyl-1 -oxopropyl]glycine (REV 3659-(S), pivopril). Structure-activity relationships are discussed.

  DOI：

  10.1021/jm00379a013
• 作为产物：
  描述：

  6,6-二甲基二环[3.1.1]庚烷-2-酮 生成 nopinylamine
  参考文献：
  名称：

  Indyk,H.; Whittaker,D., Journal of the Chemical Society. Perkin transactions II, 1974, p. 646 - 650

  摘要：

  DOI：

文献信息

• Discovery of a novel series of 6-azauracil-based thyroid hormone receptor ligands: potent, TRβ subtype-selective thyromimetics
  作者：Robert L. Dow、Steven R. Schneider、Ernest S. Paight、Richard F. Hank、Phoebe Chiang、Peter Cornelius、Eunsun Lee、William P. Newsome、Andrew G. Swick、Josephine Spitzer、Diane M. Hargrove、Terrell A. Patterson、Jayvardhan Pandit、Boris A. Chrunyk、Peter K. LeMotte、Dennis E. Danley、Michele H. Rosner、Mark J. Ammirati、Samuel P. Simons、Gayle K. Schulte、Bonnie F. Tate、Paul DaSilva-Jardine

  DOI：10.1016/s0960-894x(02)00947-2

  日期：2003.2

  In this communication, we wish to describe the discovery of a novel series of 6-azauracil-based thyromimetics that possess up to 100-fold selectivities for binding and functional activation of the beta(1)-isoform of the thyroid receptor family. Structure-activity relationship studies on the 3,5- and 3'-positions provided compounds with enhanced TRbeta affinity and selectivity. Key binding interactions between the 6-azauracil moiety and the receptor have been determined through of X-ray crystallographic analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Stereospecific Hydrogenation of α-Pinene Derivatives
  作者：G. W. Eigenmann、R. T. Arnold

  DOI：10.1021/ja01522a072

  日期：1959.7
• Ipaktschi, Junes, Chemische Berichte, 1984, vol. 117, # 2, p. 856 - 858
  作者：Ipaktschi, Junes

  DOI：——

  日期：——
• Rueck-Braun, Karola; Martin, Til; Mikulas, Mark, Chemistry - A European Journal, 1999, vol. 5, # 3, p. 1028 - 1037
  作者：Rueck-Braun, Karola、Martin, Til、Mikulas, Mark

  DOI：——

  日期：——
• Angiotensin-converting enzyme inhibitors. New orally active antihypertensive (mercaptoalkanoyl)- and [(acylthio)alkanoyl]glycine derivatives
  作者：John T. Suh、Jerry W. Skiles、Bruce E. Williams、Raymond D. Youssefyeh、Howard Jones、Bernard Loev、Edward S. Neiss、Alfred Schwab、William S. Mann

  DOI：10.1021/jm00379a013

  日期：1985.1

  A variety of N-substituted (mercaptoalkanoyl)- and [(acylthio)alkanoyl]glycine derivatives was synthesized and their ability in inhibiting the activity of angiotensin-converting enzyme (ACE) was examined in vitro and in vivo. The acylthio derivatives prepared are assumed to act as prodrugs since they are much less active than the corresponding free SH compounds in vitro and can be expected to act in vivo only after conversion to the free sulfhydryl compounds. A number of these compounds are potent ACE inhibitors that lowered blood pressure in Na-deficient, conscious spontaneously hypertensive rats (SHR), a high renin model. One of the most active members of the series was (S)-N-cyclopentyl-N-[3-[(2,2-dimethyl-1-oxopropyl)thio]-2-methyl-1 -oxopropyl]glycine (REV 3659-(S), pivopril). Structure-activity relationships are discussed.