(R)-2-Amino-1-propane | 74474-93-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-Amino-1-propane
• 英文别名: N¹,N¹-dibenzyl-1,2-propanediamine；(2R)-1-N,1-N-dibenzylpropane-1,2-diamine
• CAS: 74474-93-4
• 化学式: C₁₇H₂₂N₂
• 分子量: 254.375
• InChiKey: DHBQPTRGHHYJFB-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-Amino-1-propane 在 palladium(II) hydroxide/carbon 盐酸 、 硼烷四氢呋喃络合物 、 三氟甲磺酸酐 、 氢气 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 反应 63.34h， 生成 (3R,5r)-1-苄基-3,5-二甲基哌嗪
  参考文献：
  名称：

  [EN] PIPERAZINE UREA DERIVATIVES AS MELANOCORTIN-4 RECEPTOR AGONISTS
  [FR] DERIVES D'UREE DE PIPERAZINE UTILISES COMME AGONISTES DES RECEPTEURS DE MELANOCORTINE-4

  摘要：

  某些新型哌嗪脲衍生物是人类黑色素皮质素-4受体（MC-4R）的激动剂，特别是MC-4R的受体亚型选择性激动剂。它们对于治疗、控制或预防对MC-4R激活敏感的疾病和疾病是有用的，例如肥胖症和糖尿病。

  公开号：

  WO2004024720A1
• 作为产物：
  描述：

  苯甲醛 在 盐酸 、 10% palladium on active carbon 、 氢气 、 三乙胺 作用下， 以 苯 为溶剂， 生成 (R)-2-Amino-1-propane
  参考文献：
  名称：

  Kurganov, Alexandr; Zhuchkova, Lydmila; Davankov, Vadim, Liebigs Annalen der Chemie, 1980, # 5, p. 786 - 790

  摘要：

  DOI：

文献信息

• [EN] PIPERAZINE UREA DERIVATIVES AS MELANOCORTIN-4 RECEPTOR AGONISTS<br/>[FR] DERIVES D'UREE DE PIPERAZINE UTILISES COMME AGONISTES DES RECEPTEURS DE MELANOCORTINE-4
  申请人：MERCK & CO INC

  公开号：WO2004024720A1

  公开（公告）日：2004-03-25

  Certain novel piperazine urea derivatives are agonists of the human melanocortin-4 receptor (MC-4R) and, in particular, are receptor-subtype selective agonists of MC-4R. They are useful for the treatment, control, or prevention of diseases and disorders responsive to the activation of MC-4R, such as obesity and diabetes.

  某些新型哌嗪脲衍生物是人类黑色素皮质素-4受体（MC-4R）的激动剂，特别是MC-4R的受体亚型选择性激动剂。它们对于治疗、控制或预防对MC-4R激活敏感的疾病和疾病是有用的，例如肥胖症和糖尿病。
• Asymmetric Synthesis of 2,6-Methylated Piperazines
  作者：John W. Mickelson、Kenneth L. Belonga、E. Jon Jacobsen

  DOI：10.1021/jo00118a039

  日期：1995.6

  The complete series of enantiopure 2,6-methylated piperazines was synthesized utilizing two alternative reactions in the key bond-forming step. The dimethyl enantiomers, (2R,6R)- and (2S,6S)-2,6-dimethylpiperazine (1, 2), were prepared using either a diastereoselective triflate alkylation or a novel intramolecular Mitsunobu reaction to set the required stereochemistry. The monomethyl derivatives, (R)- and (S)-tert-butyl 2-methyl-1-piperazinecarboxylate (3, 4) were also synthesized employing the Mitsunobu cyclization strategy while the trimethyl compounds, (R)- and (S)-2,2,6-trimethylpiperazine (5, 6) were prepared using an enantiospecific triflate alkylation as the principal reaction. These methods represent efficient, general strategies for preparing a variety of 2,6-methylated piperazines for which the absolute stereochemistry can be readily controlled.
• Asymmetric synthesis of (2R,6R) and (2S,6S)-2,6-dimethylpiperazine
  作者：John W. Mickelson、E.Jon Jacobsen

  DOI：10.1016/0957-4166(94)00341-8

  日期：1995.1

  The title compounds were prepared via two efficient routes. The first sequence utilized a diastereospecific triflate alkylation in the key bond forming step while the second method relied on a novel intramolecular Mitsunobu reaction to set the required stereochemistry
• US7414057B2
  申请人：——

  公开号：US7414057B2

  公开（公告）日：2008-08-19
• Discovery of a piperazine urea based compound as a potent, selective, orally bioavailable melanocortin subtype-4 receptor partial agonist
  作者：Qingmei Hong、Raman K. Bakshi、Brenda L. Palucki、Min K. Park、Zhixiong Ye、Shuwen He、Patrick G. Pollard、Iyassu K. Sebhat、Jian Liu、Liangqin Guo、Doreen E. Cashen、William J. Martin、David H. Weinberg、Tanya MacNeil、Rui Tang、Constantin Tamvakopoulos、Qianping Peng、Randy R. Miller、Ralph A. Stearns、Howard Y. Chen、Airu S. Chen、Alison M. Strack、Tung M. Fong、D. Euan MacIntyre、Matthew J. Wyvratt、Ravi P. Nargund

  DOI：10.1016/j.bmcl.2011.02.090

  日期：2011.4

  We report the discovery of piperazine urea based compound 1, a potent, selective, orally bioavailable melanocortin subtype-4 receptor partial agonist. Compound 1 shows anti-obesity efficacy without potentiating erectile activity in the rodent models. (C) 2011 Elsevier Ltd. All rights reserved.