(S)-1-(2-Pyridyl)-2-phenylethylamine | 145165-97-5

• 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: (S)-1-(2-Pyridyl)-2-phenylethylamine
• 英文别名: (I+/-S)-I+/--(Phenylmethyl)-2-pyridinemethanamine；(1S)-2-phenyl-1-pyridin-2-ylethanamine
• CAS: 145165-97-5
• 化学式: C₁₃H₁₄N₂
• 分子量: 198.268
• InChiKey: UVVZCVILTRYDBS-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-(2-Pyridyl)-2-phenylethylamine 在 盐酸 、 4-二甲氨基吡啶 、 TEA 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-N-((S)-2-phenyl-1-pyridin-2-yl-ethyl)-propionamide
  参考文献：
  名称：

  A New Asymmetric Synthesis of (S)-Dolaphenine and Its Heteroaromatic Congeners Utilizing (+)-2-Hydroxy-3-pinanone and (−)-3-Hydroxy-2-caranone as Chiral Auxiliaries

  摘要：

  (+)-2-羟基-3-子戊酮 ((+)-HyPN, (+)-2a) 和 (-)-3-羟基-2-赤霉酸 ((-)-2b) 分别与 1-(2-噻唑基)甲胺 (17) 反应，生成相应的席夫碱 18a 和 18b。随后进行烷基化，去除手性助剂 (+)-2a 和 (-)-2b，得到光学纯的 (S)-多拉苯胺 (10)。该方法被应用于多拉苯胺类似物 27a-d 的不对称合成。

  DOI：

  10.1016/0040-4020(95)00828-v
• 作为产物：
  描述：

  (1S,2S,5S)-2,6,6-Trimethyl-3-[(Z)-pyridin-2-ylmethylimino]-bicyclo[3.1.1]heptan-2-ol 在 正丁基锂 、 羟胺乙酸盐 作用下， 以 乙醇 为溶剂， 反应 27.0h， 生成 (S)-1-(2-Pyridyl)-2-phenylethylamine
  参考文献：
  名称：

  Aiqiao, Mi; Xun, Xiao; Lanjun, Wu, Synthetic Communications, 1991, vol. 21, # 21, p. 2207 - 2212

  摘要：

  DOI：

文献信息

• Conformational control of propeller-like chirality in Zn(II) complexes: Tightly balanced steric bias
  作者：Yu-Hung Chiu、Osvaldo dos Santos、James W Canary

  DOI：10.1016/s0040-4020(99)00713-9

  日期：1999.10

  The conformational behavior of a series of chiral tripodal ligand-Zn(II) complexes was examined. The ligands adopt propeller-like conformations upon complexation of trigonal bipyramidal metal ions such as Zn(II), with the chirality of the propeller determined by the absolute configuration of a single chiral center in one of the tripod arms. Surprisingly, increasing the size of the substituent in the

  检查了一系列手性三脚架配体-Zn（II）配合物的构象行为。配体在与三角双锥体金属离子（例如Zn（II））络合时采用螺旋桨状构象，螺旋桨的手性由三脚架臂之一中单个手性中心的绝对构型决定。出人意料的是，增加手性臂中取代基的尺寸并不能改善复合物的几何定义，如复合物的圆二色性光谱所示。
• Addition of Organozincate Reagents to Imines Derived from (S)-1-Phenylethylamine and Ethyl (S)-Valinate—Synthesis of (S)-1-(2-Pyridyl)Alkylamines
  作者：Giuseppe Alvaro、Paolo Pacioni、Diego Savoia

  DOI：10.1002/chem.19970030512

  日期：1997.5

  AbstractTriorganozincates were added to aliphatic aldimines derived from (S)‐1‐phenylethylamine and (S‐valine esters in the presence of boron trifluoride to give secondary amines with low diastereoselectivies. From mixed zincates, most alkyl groups (methyl, ethyl, 1‐heptynyl, but not tert‐butyl) could be transferred. No addition to benzaldimines was observed, but the imines prepared from 2‐pyridinecarboxaldehyde did not require activation by BF3 and underwent selective group transfer from mixed zincates at — 78°C. Excellent diastereoselectivities were observed in the reactions of the 2‐pyridine imine derived from ethyl (S)‐valinate with mixed zincates, in which the methyl group was used as nontransferable ligand, allowing the transfer of alkyl and vinyl groups with excellent to complete selectivity. However, dimethyl(aryl)‐ and dimethyl‐(1‐heptynyl)zincates did not react. (S)‐1‐(2‐Pyridyl)alkylamines were prepared with high optical purity by subsequent removal of the chiral auxiliary.
• A New Asymmetric Synthesis of (S)-Dolaphenine and Its Heteroaromatic Congeners Utilizing (+)-2-Hydroxy-3-pinanone and (−)-3-Hydroxy-2-caranone as Chiral Auxiliaries
  作者：Naoko Irako、Yasumasa Hamada、Takayuki Shioiri

  DOI：10.1016/0040-4020(95)00828-v

  日期：1995.11

  (+)-2-Hydroxy-3-pinanone ((+)-HyPN, (+)-2a) and (-)-3-hydroxy-2-caranone ((-)-2b) were respectively converted to the corresponding Schiff bases 18a and 18b with 1-(2-thiazolyl)methyiamine (17). Alkylation followed by removal of the chiral auxiliaries (+)-2a and (-)-2b afforded (S)-dolaphenine (10) as an optically pure form. The method was applied to the asymmetric synthesis of the dolaphenine analogs 27a-d.

  (+)-2-羟基-3-子戊酮 ((+)-HyPN, (+)-2a) 和 (-)-3-羟基-2-赤霉酸 ((-)-2b) 分别与 1-(2-噻唑基)甲胺 (17) 反应，生成相应的席夫碱 18a 和 18b。随后进行烷基化，去除手性助剂 (+)-2a 和 (-)-2b，得到光学纯的 (S)-多拉苯胺 (10)。该方法被应用于多拉苯胺类似物 27a-d 的不对称合成。
• Aiqiao, Mi; Xun, Xiao; Lanjun, Wu, Synthetic Communications, 1991, vol. 21, # 21, p. 2207 - 2212
  作者：Aiqiao, Mi、Xun, Xiao、Lanjun, Wu、Yaozhong, Jiang

  DOI：——

  日期：——