(R)-(-)-N-新戊基-1-苯基-2-(1-吡啶烷)乙胺 | 153837-28-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (R)-(-)-N-新戊基-1-苯基-2-(1-吡啶烷)乙胺
• 中文别名: N-新戊基-1-苯基-2-(1-吡啶烷)乙胺；(R)-(-)-N-新戊基-1-苯基-2-(1-吡啶烷）乙胺
• 英文名称: (2,2-Me2-propyl)-((R)-1-phenyl-2-piperidin-1-yl-ethyl)-amine
• 英文别名: (R)-N-(2,2-dimethylpropyl)-1-phenyl-2-piperidinoethylamine；(2R)-5,5-dimethyl-2-phenyl-1-(N-piperidinyl)-3-azahexane；(R)-(piperidin-1-yl)-CH2(Ph)NHCH2-tBu；(R)-2,2-Dimethyl-N-(1-phenyl-2-(piperidin-1-yl)ethyl)propan-1-amine；2,2-dimethyl-N-[(1R)-1-phenyl-2-piperidin-1-ylethyl]propan-1-amine
• CAS: 153837-28-6
• 化学式: C₁₈H₃₀N₂
• 分子量: 274.45
• InChiKey: RUWFXOINQANLGF-KRWDZBQOSA-N

物化性质

• 熔点：
  36-40°C
• 沸点：
  367.7±22.0 °C(Predicted)
• 密度：
  0.953±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  避免与氧化物、空气和酸接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  8
• 危险类别码：
  R34
• 危险品运输编号：
  UN 2735
• 海关编码：
  2933399090
• 包装等级：
  II
• 危险类别：
  8
• 安全说明：
  S26,S36/37/39,S45

反应信息

• 作为反应物：
  描述：

  (R)-(-)-N-新戊基-1-苯基-2-(1-吡啶烷)乙胺 在 正丁基锂 作用下， 以 乙醚 、 正己烷 、 甲苯 为溶剂， 生成 lithium (R)-N-neopentyl-1-phenyl-2-piperidinoethylamide
  参考文献：
  名称：

  立体选择性反应。26.手性双齿氨基锂锂在去质子化反应中与溶剂依赖性对映选择性有关的溶液结构

  摘要：

  标记的手性二齿氨基锂锂的6 Li和15 N-NMR光谱分析表明，它在THF和DME中以螯合单体（5）的形式存在，在甲苯和乙醚中以螯合二聚物（6）的形式存在，在2当量的HMPA存在下，在任何一种溶剂中作为螯合单体（5）。（R）-1对4-叔丁基环己酮（2）进行质子化的溶剂依赖性对映选择性似乎与这些溶液结构相关。

  DOI：

  10.1016/s0040-4020(97)00422-5
• 作为产物：
  描述：

  (R)-(1-amino-1-phenyl)ethyl-1-piperidine 在 sodium tetrahydroborate 、 sodium sulfate 作用下， 以 乙醇 、 苯 为溶剂， 反应 3.5h， 生成 (R)-(-)-N-新戊基-1-苯基-2-(1-吡啶烷)乙胺
  参考文献：
  名称：

  Stereoselective Reactions. XXII. Design and Synthesis of Chiral Chelated Lithium Amides for Enantioselective Reactions.

  摘要：

  从(R)-苯甘氨酸开始，设计并合成了手性螯合锂酰胺（(R)）-1a-g）的光学纯品。

  DOI：

  10.1248/cpb.42.690
• 作为试剂：
  描述：

  氰基甲酸甲酯 、 托品酮 在 正丁基锂 、 (R)-(-)-N-新戊基-1-苯基-2-(1-吡啶烷)乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以80%的产率得到S-(-)-carbomethoxytropinone
  参考文献：
  名称：

  Structure−Activity Relationship Comparison of (S)-2β-Substituted 3α-(Bis[4-fluorophenyl]methoxy)tropanes and (R)-2β-Substituted 3β-(3,4-Dichlorophenyl)tropanes at the Dopamine Transporter

  摘要：

  Extensive structure-activity relationships at the dopamine transporter (DAT) have been developed around two classes of tropane-based ligands. Opposing stereoselectivity and divergent structural requirements for optimal DAT binding suggest that these tropane-based DAT inhibitors may not access identical binding domains. To further investigate this hypothesis, a series of (S)-2beta-carboalkoxy-3alpha-(bis[4-fluorophenyl]methoxy)tropanes (11a-f, 13-16) and their identically (R)-2beta-substituted 3beta-(3,4-dichlorophenyl)tropanes (3, 5a-d) were prepared and evaluated for binding at the DAT and for inhibition of [H-3]dopamine uptake in rat brain. These studies showed that most of the identically 2-carboalkoxy-substituted analogues, within the two classes of compounds, bind with high affinity to DAT (K-i = 5.5 - 100 nM), albeit with opposite stereochemistry. However, the larger azido- (15) and isothiocyanato- (16) (S)-2beta-carbophenylethoxy-3alpha-(bis [4-fluorophenyl] methoxy)tropanes demonstrated a significant decrease in DAT binding potency (IC50 = 210 and 537 nM, respectively), suggesting that the DAT does not tolerate 2-position steric bulk in the benztropine class, as it does with the 2-substituted 3-aryltropanes. In addition, binding affinities at the serotonin transporter, norepinephrine transporter, and muscarinic receptors were evaluated and compared for compounds 2, 3, 11a-e, and 13. Together, the binding profiles across these systems demonstrated significant differences between these two classes of tropane-based ligands, which may be exploited toward the discovery of a cocaine-abuse pharmacotherapeutic.

  DOI：

  10.1021/jm0300375

文献信息

• Practical One-Step Synthesis of Koga's Chiral Bases
  作者：Eric Curthbertson、Peter O'Brien、Timothy D. Towers

  DOI：10.1055/s-2001-12768

  日期：——

  A simple, efficient and practical method for the preparation of Koga"s chiral bases is described. The method involves attack of an amine on a styrene oxide-derived aziridinium ion and has allowed the synthesis of novel diamines which cannot be prepared using Koga"s original route.

  描述了一种简单、高效和实用的Koga手性碱的制备方法。该方法涉及胺对源自苯乙烯氧化物的氮杂环的攻击，并使得合成了无法通过Koga原始路线制备的新型二胺。
• Stereoselective reactions. 26. Solution structures of chiral bidentate lithium amide in relation to the solvent-dependent enantioselectivities in deprotonation reaction
  作者：Daisaku Sato、Hisashi Kawasaki、Ichio Shimada、Yoji Arata、Kimio Okamura、Tadamasa Date、Kenji Koga

  DOI：10.1016/s0040-4020(97)00422-5

  日期：1997.5

  and 15N-NMR spectroscopic analyses of a labeled chiral bidentate lithium amide () have shown that it exists as a chelated monomer (5) in THF and in DME, as a chelated dimer (6) in toluene and in ether, while as a chelated monomer (5) in any of these solvents in the presence of 2 equivalents of HMPA. Solvent-dependent enantioselectivities in deprotonation of 4-tert-butylcyclohexanone (2) by (R)-1 appear

  标记的手性二齿氨基锂锂的6 Li和15 N-NMR光谱分析表明，它在THF和DME中以螯合单体（5）的形式存在，在甲苯和乙醚中以螯合二聚物（6）的形式存在，在2当量的HMPA存在下，在任何一种溶剂中作为螯合单体（5）。（R）-1对4-叔丁基环己酮（2）进行质子化的溶剂依赖性对映选择性似乎与这些溶液结构相关。
• Stereoselective Reactions. XXII. Design and Synthesis of Chiral Chelated Lithium Amides for Enantioselective Reactions.
  作者：Ryuichi SHIRAI、Kazumasa AOKI、Daisaku SATO、Hee-Doo KIM、Masatoshi MURAKATA、Tatsuro YASUKATA、Kenji KOGA

  DOI：10.1248/cpb.42.690

  日期：——

  Chiral chelated lithium amides ((R))-1a-g) were designed and synthesized in optically pure forms starting from (R)-phenylglycine.

  从(R)-苯甘氨酸开始，设计并合成了手性螯合锂酰胺（(R)）-1a-g）的光学纯品。