(αR,2S)-1-methyl-α-phenyl-2-pyrrolidinemethanol | 110529-23-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (αR,2S)-1-methyl-α-phenyl-2-pyrrolidinemethanol
• 英文别名: (1R,2'S)-(-)-phenyl(1-methylpyrrolidin-2-yl)methanol；(R)-((S)-1-methylpyrrolidin-2-yl)(phenyl)methanol；(1'R,2S')-Phenyl-N-methyl-2-pyrrolidinemethanol；(R)-[(2S)-1-methylpyrrolidin-2-yl]-phenylmethanol
• CAS: 110529-23-2
• 化学式: C₁₂H₁₇NO
• 分子量: 191.273
• InChiKey: RLGNUDZFWFQELR-NWDGAFQWSA-N

物化性质

• 沸点：
  296.2±13.0 °C(Predicted)
• 密度：
  1.084±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (αR,2S)-1-methyl-α-phenyl-2-pyrrolidinemethanol 在 三乙胺 、 三氟乙酸酐 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 50.0h， 以72%的产率得到(2S,3R)-1-methyl-2-phenylpiperidin-3-ol
  参考文献：
  名称：

  Highly Stereoselective Syntheses of Proline-Derived Vicinal Amino Alcohols through Grignard Addition onto N-Tosylprolinal

  摘要：

  A highly diastereoselective Grignard addition to N-tosyl-l-prolinal has been developed to deliver a variety of proline-derived vicinal amino alcohols in good to excellent yields with high diastereoselectivities. A similar selectivity was also obtained by using N-tosyl-d-prolinal. The methodology has been applied to the synthesis of medicinally important 3-hydroxy-2-phenylpiperidines.

  DOI：

  10.1055/s-0035-1560802
• 作为产物：
  描述：

  L-吡咯烷-1,2-二羧酸-1-乙酯 在 氢氧化钾 、 三氯化铝 、 甲酸 、 草酰氯 、 二异丁基氢化铝 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 (αR,2S)-1-methyl-α-phenyl-2-pyrrolidinemethanol
  参考文献：
  名称：

  Catalytic asymmetric induction. Highly enantioselective addition of dialkylzincs to aldehydes using chiral pyrrolidinylmethanols and their metal salts

  摘要：

  DOI：

  10.1021/ja00257a034
• 作为试剂：
  描述：

  反式肉桂醛 、 Dimethylzinc 在 (αR,2S)-1-methyl-α-phenyl-2-pyrrolidinemethanol 正丁基锂 作用下， 生成 (2R,3E)-4-phenyl-3-buten-2-ol 、 (S)-(E)-4-phenyl-3-buten-2-ol
  参考文献：
  名称：

  Catalytic asymmetric induction. Highly enantioselective addition of dialkylzincs to aldehydes using chiral pyrrolidinylmethanols and their metal salts

  摘要：

  DOI：

  10.1021/ja00257a034

文献信息

• Complementary catalytic asymmetric induction in the enantioselective addition of diethylzinc to aldehydes
  作者：Kenso Soai、Atsuhiro Ookawa、Kazuo Ogawa、Tatsuya Kaba

  DOI：10.1039/c39870000467

  日期：——

  Both enantiomers of sec-alcohols were obtained in high enantiomeric excess (up to 92%) from the enantioselective addition of diethylzinc to aldehydes using chiral pyrrolidinylmethanol derivatives as catalysts.

  仲醇的两种对映异构体均以对映体过量（最高为92％）通过使用手性吡咯烷二甲醇甲醇衍生物作为催化剂将二乙基锌对醛选择性地加成到醛中而制得。
• Enantioselective Bromolactonization Using an<i>S</i>-Alkyl Thiocarbamate Catalyst
  作者：Xiaojian Jiang、Chong Kiat Tan、Ling Zhou、Ying-Yeung Yeung

  DOI：10.1002/anie.201202079

  日期：2012.7.27

  The apple never falls far from the tree: S‐alkyl thiocarbamate 1 (see scheme, NBP=N‐bromophthalimide) was prepared in high yield through a synthetic sequence involving a Newman–Kwart rearrangement of the corresponding O‐alkyl thiocarbamates. Compound 1 was used to catalyze bromolactonization, thus providing enantioenriched δ‐lactones in excellent yield and enantioselectivity.

  苹果永远不会离树太远：通过涉及相应的O-烷基硫代氨基甲酸酯的Newman-Kwart重排的合成序列，以高收率制备了S-烷基硫代氨基甲酸酯1（参见方案，NBP = N-溴邻苯二甲酰亚胺）。化合物1用于催化溴化内酯化，从而以优异的收率和对映选择性提供了对映体富集的δ-内酯。
• Alkylation of 2-lithio-N-methylpiperidines and -pyrrolidines: scope, limitations, and stereochemistry
  作者：Robert E. Gawley、Qianhui Zhang

  DOI：10.1021/jo00123a008

  日期：1995.9

  The scope and limitations of the alkylation of racemic and nonracemic 2-lithiopiperidines and -pyrrolidines, obtained by transmetalation of the corresponding stannanes, is reported. These organolithiums react with a variety of electrophiles to afford 2-substituted pyrrolidines and piperidines in excellent yield. With primary alkyl halides the reaction proceeds with net inversion of configuration at the metal-bearing carbon in the piperidines; in the pyrrolidines there is a mixture of inversion and retention, with the former predominating. With most carbonyl electrophiles (carbon dioxide, dimethyl carbonate, methyl chloroformate, pivaloyl chloride, benzaldehyde, and dialkyl ketones), retention is observed in both cases. Electrophiles such as benzophenone, benzyl bromide, and tert-butyl bromoacetate afford racemic coupling products. A mechanistic interpretation is presented.
• <i>N</i>-Tritylprolinal:  An Efficient Building Block for the Stereoselective Synthesis of Proline-Derived Amino Alcohols
  作者：Joseph Bejjani、Fabrice Chemla、Max Audouin

  DOI：10.1021/jo034976g

  日期：2003.12.1

  N-Tritylprolinal (prepared in four steps from L-proline) shows a very high Felkin diastereoselectivity in its reaction with various nucleophiles, leading to a straightforward and highly stereoselective access to syn-proline-derived amino alcohols.
• SOAI KENSO; OOKAWA ATSUHIRO; OGAWA KAZUO; KABA TATSUYA, J. CHEM. SOC. CHEM. COMMUN.,(1987) N 6, 467-468
  作者：SOAI KENSO、 OOKAWA ATSUHIRO、 OGAWA KAZUO、 KABA TATSUYA

  DOI：——

  日期：——