((2R)-butylpyrrolidin-1-yl)-(1'R)-phenylethan-2-ol | 116830-34-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: ((2R)-butylpyrrolidin-1-yl)-(1'R)-phenylethan-2-ol
• 英文别名: (-)-N-<2-(1-Hydroxy-2(R)-phenylethyl)>-5(R)-butyl-2-pyrrolidine；(2R)-2-[(2'R)-2'-butyl-N-pyrrolidinyl]-2-phenyl-1-ethanol；(2R)-2-[(2R)-2-butylpyrrolidin-1-yl]-2-phenylethanol
• CAS: 116830-34-3
• 化学式: C₁₆H₂₅NO
• 分子量: 247.381
• InChiKey: BRSJAPJEPKZUHQ-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ((2R)-butylpyrrolidin-1-yl)-(1'R)-phenylethan-2-ol 在 palladium on activated charcoal 氢气 作用下， 生成 (2R)-2-Butylpyrrolidine
  参考文献：
  名称：

  2-烷基吡咯烷的不对称合成XIII合成：走向氮杂双环系统

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(00)80168-9
• 作为产物：
  描述：

  (3R-顺)-(-)-3-苯基四氢吡咯并-[2,1-B]唑-5(6H)-酮 在 lithium aluminium tetrahydride 、 copper(I) bromide dimethylsulfide complex 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 30.33h， 生成 ((2R)-butylpyrrolidin-1-yl)-(1'R)-phenylethan-2-ol
  参考文献：
  名称：

  Asymmetric synthesis of 5-substituted pyrrolidinones via a chiral N-acyliminium equivalent

  摘要：

  5-Substituted pyrrolidinones 5 were synthesized in good yields and with fair to good diastereoselectivities from the chiral non-racemic oxazolopyrrolidinone 4. Various nucleophiles including cuprates, silanes and phosphites were used. The chiral induction is thought to arise from a chelated N-acyliminium species. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00195-1

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 from 3-acylpropionic acids
  作者：A. I. Meyers、Laurence E. Burgess

  DOI：10.1021/jo00007a011

  日期：1991.3

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

  DOI：——

  日期：——