(-)-N-<2-(1-Hydroxy-2(R)-phenylethyl)>-5(R)-heptyl-2-pyrrolidine | 116830-36-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (-)-N-<2-(1-Hydroxy-2(R)-phenylethyl)>-5(R)-heptyl-2-pyrrolidine
• 英文别名: (2R)-2-[(2R)-2-heptylpyrrolidin-1-yl]-2-phenylethanol
• CAS: 116830-36-5
• 化学式: C₁₉H₃₁NO
• 分子量: 289.461
• InChiKey: VJMQVCGEAXVXOE-MOPGFXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  21.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  23.47
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (-)-N-<2-(1-Hydroxy-2(R)-phenylethyl)>-5(R)-heptyl-2-pyrrolidine 生成 (S)-2-heptylpyrrolidine
  参考文献：
  名称：

  ARSENIYADIS, S.;HUANG, P. Q.;HUSSON, H. -P., TETRAHEDRON LETT., 29,(1988) N 6, 631-634

  摘要：

  DOI：
• 作为产物：
  描述：

  (-)-(3R,7aS)-3-Phenyl-5-oxo-7a-heptyl-2,3,5,6,7,7a-hexahydropyrrolo<2,1-b>oxazole 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到(-)-N-<2-(1-Hydroxy-2(R)-phenylethyl)>-5(R)-heptyl-2-pyrrolidine
  参考文献：
  名称：

  A simple asymmetric synthesis of 2-substituted pyrrolidines from 3-acylpropionic acids

  摘要：

  The title compounds have been prepared from 3-acylpropionic acids 2 and (-)-R-phenylglycinol in a three-step sequence in > 98% enantiomeric excess. The R group in 2 ultimately becomes the 2-substituent in the chiral pyrrolidine.

  DOI：

  10.1021/jo00007a011

文献信息

• Asymmetric synthesis XIII synthesis of 2-alkylpyrrolidines: Towards azabicyclic systems
  作者：S. Arseniyadis、P.Q. Huang、H.-P. Husson

  DOI：10.1016/s0040-4039(00)80168-9

  日期：——

  The enantiospecific synthesis of a series of 2(S)-alkylpyrrolidines from 2-cyano oxazolopyrrolidine synthon is described. Two of the synthesised compounds represent key intermediates towards ozabicyclic alkaloids.

  描述了由2-氰基恶唑并吡咯烷合子合成一系列2（S）-烷基吡咯烷的对映体特异性。两种合成的化合物代表了向氮杂双环生物碱的关键中间体。
• A simple asymmetric synthesis of 2-substituted pyrrolidines and 5-substituted pyrrolidinones
  作者：Laurence E. Burgess、A. I. Meyers

  DOI：10.1021/jo00032a012

  日期：1992.3

  An efficient procedure for the preparation of the title compounds in high enantiomeric purity has been realized starting from 3-acylpropionic acids. Stereoselective reduction of chiral bicyclic lactams 2a-h, prepared from the corresponding gamma-keto acid and (R)-phenylglycinol, using alane or triethylsilane with titanium tetrachloride provided the N-substituted pyrrolidines and pyrrolidinones, respectively. Subsequent cleavage of the phenylglycinol returned the desired amines and lactams. The enantiomeric purity of these compounds was determined to be > 98% by chiral stationary-phase HPLC.
• MEYERS, A. I.;BURGESS, LAURENCE E., J. ORG. CHEM., 56,(1991) N, C. 2294-2296
  作者：MEYERS, A. I.、BURGESS, LAURENCE E.

  DOI：——

  日期：——