(-)(rel-1R,2R)-1-phenyl-2-piperidino-propan-1-ol | 25394-32-5

• 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: (-)(rel-1R,2R)-1-phenyl-2-piperidino-propan-1-ol
• 英文别名: (1R,2S)-1-phenyl-2-piperidin-1-ylpropan-1-ol
• CAS: 25394-32-5；56571-89-2；56571-90-5；69858-34-0；69858-35-1；133576-75-7；133576-76-8
• 化学式: C₁₄H₂₁NO
• 分子量: 219.327
• InChiKey: CYPOTTRENVPAPL-JSGCOSHPSA-N

物化性质

• 熔点：
  106-107 °C
• 沸点：
  338.5±22.0 °C(Predicted)
• 密度：
  1.051±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  (-)(rel-1R,2R)-1-phenyl-2-piperidino-propan-1-ol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 (1R,2S)-2-(1-piperidino)-1-phenyl-1-N-phthalimidohydroxypropane
  参考文献：
  名称：

  Dieter, R. Karl; Datar, Ravindra, Canadian Journal of Chemistry, 1993, vol. 71, # 6, p. 814 - 823

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 生成 (-)(rel-1R,2R)-1-phenyl-2-piperidino-propan-1-ol
  参考文献：
  名称：

  Takamatsu, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1956, vol. 76, p. 1227

  摘要：

  DOI：
• 作为试剂：
  描述：

  4-甲氧基苯甲醛 、 苯硼酸 在 diethylzinc 、 (-)(rel-1R,2R)-1-phenyl-2-piperidino-propan-1-ol 作用下， 以 甲苯 为溶剂， 反应 13.33h， 生成 (S)-(4-methoxyphenyl)phenylmethanol 、 (R)-(4-methoxyphenyl)phenylmethanol
  参考文献：
  名称：

  Highly Enantioselective Aryl Transfer to Aldehydes:  A Remarkable Effect of Sulfur Substitution in Amino Thioacetate Ligands

  摘要：

  Chiral amino thioacetate ligands were prepared from the corresponding amino alcohols and used as catalysts for enantioselective aryl transfer reaction. The amino thioacetates were remarkably superior to the corresponding amino alcohols, Low catalyst loadings of only 1-2.5 mol % were sufficient to achieve excellent enantioselectivity as well as high conversion in short reaction time. The results reveal that the thioacetoxy moiety of the amino thioacetates has a surprisingly beneficial effect in enhancing the asymmetric induction.

  DOI：

  10.1021/ol8001249

文献信息

• Enantioselective addition of diethylzinc to α-branched aldehydes
  作者：Jahyo Kang、Jun Won Lee、Joo In Kim

  DOI：10.1039/c39940002009

  日期：——

  Reaction of diethylzinc with α-branched aldehydes in the presence of a catalytic amount of (1R,2S)-(–)-1-phenyl-2-piperidinopropane-1-thiol 1 provided the corresponding secondary alcohols in almost 100% enantiomeric excess.

  在催化量的(1R,2S)-(–)-1-苯基-2-哌啶丙烷-1-硫醇1存在下，二乙基锌与α-支链醛的反应几乎以100%的外消旋过剩量提供了相应的二级醇。
• Enantioselective addition of diethylzinc to aldehydes in the presence of chiral aprotic ligands
  作者：Myung-Jong Jin、Young-Mok Kim、Kyoung-Soo Lee

  DOI：10.1016/j.tetlet.2005.02.066

  日期：2005.4

  Optically active amino thiocyanate derivatives of (−)-norephedrine were found to act as effective aprotic ligands for enantioselective addition of diethylzinc to aldehydes. This reaction provided optically active secondary alcohols with ee up to 96%.

  发现（-）-去氧麻黄碱的旋光性氨基硫氰酸酯衍生物可作为有效的非质子传递配体，用于将二乙基锌对映体选择性地加成成醛。该反应提供了具有高达96％ee的旋光仲醇。
• PREPARATION OF [R-(R,S)]-a-METHYL-a-PHENYL-1-PYRROLIDINEETHANOL
  作者：Zhao, Dalian、Chen, Cheng-yi、Xu, Feng、Tan, Lushi、Tillyer, Richard、Pierce, Michael E.、Moore, James R.、Burton, Jonathan W.、Holmes, Andrew B.

  DOI：10.15227/orgsyn.077.0012

  日期：——
• Chiral arene chromium tricarbonyl complexes as enantioselective catalysts: highly selective 1,2 alkyl additions to aldehydes
  作者：Steven B. Heaton、Graham B. Jones

  DOI：10.1016/s0040-4039(00)91708-8

  日期：1992.3

  The preparation of a rationally designed catalyst system derived from norephedrine is reported. The key stereodirective element emanates from a chromium tricarbonyl group complexed to one face of the aryl ring. The catalysts mediate the addition of diethyl zinc to a variety of aldehydes with extremely high enantioselectivity.
• New Catalysts for the Asymmetric Hydrosilylation of Ketones Discovered by Mass Spectrometry Screening
  作者：Sulan Yao、Jun-Cai Meng、Gary Siuzdak、M. G. Finn

  DOI：10.1021/jo026365e

  日期：2003.4.1

  A method for determining enantiomeric excess by mass spectrometry was employed to screen a family of chiral phosphite P,N-ligands for activity in the rhodium-catalyzed asymmetric hydro-silylation of ketones. The identification of an effective set of ligands was followed by preliminary studies of the reaction scope and mechanism. Asymmetric induction of 84-88% ee for larger-scale reactions was observed, which is close to the level of the best alternative catalysts previously discovered. The screening method was shown to be applicable to a variety of substrates without the need for special optimization.