(1S,2'S)-phenyl(1-methylpyrrolidin-2-yl)methanol | 74936-98-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1S,2'S)-phenyl(1-methylpyrrolidin-2-yl)methanol
• 英文别名: (1'S,2S')-Phenyl-N-methyl-2-pyrrolidinemethanol；(S)-[(2S)-1-methylpyrrolidin-2-yl]-phenylmethanol
• CAS: 74936-98-4
• 化学式: C₁₂H₁₇NO
• 分子量: 191.273
• InChiKey: RLGNUDZFWFQELR-RYUDHWBXSA-N

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：

  (1S,2'S)-phenyl(1-methylpyrrolidin-2-yl)methanol 、 三氟乙酸酐 在 三乙胺 、 sodium hydroxide 作用下， 反应 49.0h， 以56%的产率得到(+)-1-methyl-2-phenylpiperidin-3-ol
  参考文献：
  名称：

  扩环 – 从吡咯烷甲醇衍生物形成光学活性 3-羟基哌啶

  摘要：

  用三氟乙酸处理吡咯烷甲醇衍生物 (–)-1、(–)-6、(–)-7、8、(–)-9、(+)-10、(–)-11 和 (–)-21酸酐，然后用 Et3N，在三氟乙酰基用 NaOH 水解后，得到旋光 3-羟基哌啶 (-)-14, (+)-15, (-)-16, 17, (+)-18, (- )-19、(–)-20 和 (+)-22 分别。产率良好，对映体过量非常好（高达 95%）。

  DOI：

  10.1002/(sici)1099-0690(199907)1999:7<1693::aid-ejoc1693>3.0.co;2-j
• 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 、 potassium tri-sec-butyl-borohydride 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 (1S,2'S)-phenyl(1-methylpyrrolidin-2-yl)methanol
  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

• 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。
• Radical Hydroxyalkylation of C−H Bond Adjacent to Nitrogen of Tertiary Amides, Ureas, and Amines
  作者：Takehiko Yoshimitsu、Yoshimasa Arano、Hiroto Nagaoka

  DOI：10.1021/ja053855q

  日期：2005.8.24

  Tertiary amides, ureas, and amines undergo direct intermolecular addition to aldehydes under the Et3B/air conditions, thereby providing a unique and simple means for the radical sp3 C-H transformation of nitrogen-containing molecules.
• 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.
• Catalytic asymmetric induction. Highly enantioselective addition of dialkylzincs to aldehydes using chiral pyrrolidinylmethanols and their metal salts
  作者：Kenso Soai、Atsuhiro Ookawa、Tatsuya Kaba、Kazuo Ogawa

  DOI：10.1021/ja00257a034

  日期：1987.11
• Ring Expansion – Formation of Optically Active 3-Hydroxypiperidines from Pyrrolidinemethanol Derivatives
  作者：Janine Cossy、Cécile Dumas、Domingo Gomez Pardo

  DOI：10.1002/(sici)1099-0690(199907)1999:7<1693::aid-ejoc1693>3.0.co;2-j

  日期：1999.7

  Treatment of pyrrolidinemethanol derivatives (–)-1, (–)-6, (–)-7, 8, (–)-9, (+)-10, (–)-11, and (–)-21 with trifluoroacetic anhydride and then with Et3N afforded, after hydrolysis of the trifluoroacetyl group with NaOH, the optically active 3-hydroxypiperidines (–)-14, (+)-15, (–)-16, 17, (+)-18, (–)-19, (–)-20, and (+)-22, respectively. The yields are good and the enantiomeric excess excellent (up

  用三氟乙酸处理吡咯烷甲醇衍生物 (–)-1、(–)-6、(–)-7、8、(–)-9、(+)-10、(–)-11 和 (–)-21酸酐，然后用 Et3N，在三氟乙酰基用 NaOH 水解后，得到旋光 3-羟基哌啶 (-)-14, (+)-15, (-)-16, 17, (+)-18, (- )-19、(–)-20 和 (+)-22 分别。产率良好，对映体过量非常好（高达 95%）。