(S)-N-benzyl-2-fluoromethylpyrrolidine | 787564-48-1

• 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: (S)-N-benzyl-2-fluoromethylpyrrolidine
• 英文别名: (2S)-1-benzyl-2-fluoromethylpyrrolidine；(2S)-N-benzyl-2-fluoromethylpyrrolidine；(2S)-1-benzyl-2-(fluoromethyl)pyrrolidine
• CAS: 787564-48-1
• 化学式: C₁₂H₁₆FN
• 分子量: 193.264
• InChiKey: ABOUERVZECNFBI-LBPRGKRZSA-N

物化性质

• 沸点：
  256.9±10.0 °C(Predicted)
• 密度：
  1.046±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-N-benzyl-2-fluoromethylpyrrolidine 在 1-氯乙基氯甲酸酯 、 甲醇 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以87%的产率得到(2S)-2-(氟甲基)吡咯烷盐酸盐(1:1)
  参考文献：
  名称：

  EP1785418

  摘要：

  公开号：
• 作为产物：
  描述：

  N-苄基-L-脯氨醇 在 [双(2-甲氧基乙基)胺]三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以50%的产率得到(S)-N-benzyl-2-fluoromethylpyrrolidine
  参考文献：
  名称：

  Nucleophilic fluorination of amino alcohols and diols using Deoxofluor

  摘要：

  Various fluorinated chiral compounds were synthesized using bis(2-methoxyethyl)aminosulfur trifluoride (Deoxofluor) as a nucleophilic fluorinating reagent. Reactions of Deoxofluor (1) with amino alcohols (2a-d) and diols (2e-g) in methylene chloride at room temperature led to the formation of the corresponding fluoro derivatives (3a-g) in good yields.(C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(02)00065-9

文献信息

• PYRAZOLE DERIVATIVES
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP1762568A1

  公开（公告）日：2007-03-14

  A compound represented by formula (I): (wherein Ar1 represents a phenyl group which may have 1 to 3 substituents, or a non-substituted 5- or 6-membered aromatic heterocyclic group; Ar2 represents (i) a non-substituted phenyl group, (ii) a phenyl group which has been substituted by a lower alkyl group having 1 to 3 groups or atoms selected from among a carbamoyl group, an amino group, a hydroxyl group, a lower alkoxy group, and a halogen atom, or (iii) a 5- or 6-membered nitrogen-containing aromatic heterocyclic group which has been substituted by 1 to 3 groups or atoms selected from among a lower alkyl group, a lower alkynyl group, a lower alkanoyl group, a carbamoyl group, a cyano group, an amino group, a hydroxyl group, a lower alkoxy group, and a halogen atom; and X represents a group represented by formula (II): (wherein the ring structure represents a 4- to 7-membered heterocyclic group which may have, in addition to the nitrogen atom shown in formula (II), one heteroatom selected from among nitrogen, oxygen, and sulfur, and which may be substituted by 1 to 4 groups or atoms selected from among a lower alkyl group, a carbamoyl group, an amino group, a hydroxyl group, a lower alkoxy group, an oxo group, a lower alkanoyl group, a lower alkylsulfonyl group, and a halogen atom)), a salt thereof, a solvate of the compound or the salt, and a drug.

  由式(I)表示的化合物： （其中Ar1代表可能具有1到3个取代基的苯基，或者是非取代的5-或6-成员芳香杂环基团；Ar2代表（i）非取代的苯基团，（ii）已被1到3个来自羰胺基、氨基、羟基、低烷氧基和卤原子的群或原子取代的较低烷基基团取代的苯基团，或者（iii）已被1到3个来自低烷基基团、低炔基基团、低烷酰基团、羰胺基、氰基、氨基、羟基、低烷氧基和卤原子的群或原子取代的5-或6-成员含氮芳香杂环基团；X代表由式(II)表示的基团： （其中环结构表示可能具有除了式(II)中显示的氮原子之外，从氮、氧和硫中选择的一个杂原子的4-到7-成员杂环基团，并且可能被1到4个来自低烷基基团、羰胺基、氨基、羟基、低烷氧基、氧基、低烷酰基团、低烷基磺酰基团和卤原子的群或原子取代）），其盐，该化合物或其盐的溶剂化合物，以及药物。
• Rearrangements accompanying fluorination of 2-amino alcohols and 1,2-diols with Deoxo-Fluor™
  作者：Chengfeng Ye、Jean’ne M. Shreeve

  DOI：10.1016/j.jfluchem.2004.06.013

  日期：2004.12

  2-Amino alcohols and 1,2-diols treated with Deoxo-Fluor™ in methylene chloride resulted in the formation of rearranged major products concomitantly with minor amounts of the straightforward fluorinated replacement products in good yields.

  用Deoxo-Fluor™在二氯甲烷中处理过的2-氨基醇和1,2-二醇导致重排的主要产物的形成，并伴有少量的简单氟化替代产物，收率很高。
• [EN] BICYCLIC HETEROCYCLE COMPOUNDS AND THEIR USES IN THERAPY<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES BICYCLIQUES ET LEURS UTILISATIONS THÉRAPEUTIQUES
  申请人：ASTEX THERAPEUTICS LTD

  公开号：WO2014060770A1

  公开（公告）日：2014-04-24

  The invention relates to new bicyclic heterocycle compounds of formula (I):,to pharmaceutical compositions comprising said compounds and to the use of said compounds in the treatment of diseases, e.g. cancer.

  该发明涉及公式(I)的新的双环杂环化合物，涉及包含该化合物的药物组合物，并涉及该化合物在治疗疾病（如癌症）中的用途。
• Ring Expansion Induced by DAST: Synthesis of Substituted 3-Fluoropiperidines from Prolinols and 3-Fluoroazepanes from 2-Hydroxymethylpiperidines
  作者：Ingrid Déchamps、Domingo Gomez Pardo、Janine Cossy

  DOI：10.1002/ejoc.200700237

  日期：2007.9

  Optically active prolinols can be converted into optically active 3-fluoropiperidines by treatment with DAST. The reaction often produces 2-fluoromethylpyrrolidines as byproducts. The ring expansion was also applied to 2-hydroxypiperidines to produce 3-fluoroazepanes. The rearrangement proceeds via an aziridinium intermediate. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  光学活性脯氨醇可以通过 DAST 处理转化为光学活性 3-氟哌啶。该反应通常会产生 2-氟甲基吡咯烷作为副产物。扩环也适用于 2-羟基哌啶以产生 3-氟氮杂环庚烷。重排通过氮丙啶中间体进行。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Synthesis of Optically Active Substituted 3-Fluoropiperidines from Prolinols by Using DAST
  作者：Janine Cossy、Ingrid Déchamps、Domingo Gomez Pardo

  DOI：10.1055/s-2007-967989

  日期：2007.2

  The treatment of optically active prolinols with DAST produces optically active 3-fluoropiperidines via aziridinium intermediates.

  用 DAST 处理具有光学活性的脯氨醇，可通过氮丙啶中间体生成具有光学活性的 3-氟哌啶。