(S)-3-(4-氟苄基)-2-哌啶酮 | 483305-46-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: (S)-3-(4-氟苄基)-2-哌啶酮
• 英文名称: (S)-3-(4-fluorobenzyl)-2-piperidone
• 英文别名: (S)-3-p-fluorobenzyl-2-piperidone；(3S)-3-[(4-fluorophenyl)methyl]piperidin-2-one
• CAS: 483305-46-0
• 化学式: C₁₂H₁₄FNO
• 分子量: 207.248
• InChiKey: YZHUFKNGGSTLGQ-JTQLQIEISA-N

物化性质

• 沸点：
  379.7±15.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-3-(4-氟苄基)-2-哌啶酮 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 3.0h， 生成 (3S)-3-[(4-氟苯基)甲基]-哌啶 、 (R)-3-(4-fluorobenzyl)piperidine
  参考文献：
  名称：

  Enantioselective Hydrogenation of 3-Alkylidenelactams:  High-Throughput Screening Provides a Surprising Solution

  摘要：

  High-throughput screening of 256 potential catalysts (8 metal precursors x 32 phosphine ligands) has identified [(BDPP)Ir(COD)]BF4 as a catalyst for the enantioselective hydrogenation of 3-alkylidenelactams. This result is surprising given the highly flexible backbone of the BDPP ligand and the ineffectiveness of this catalyst in other applications. The asymmetric hydrogenation appears fairly general for five- and six-membered lactams and in one case has been scaled up to a 20 kg level.

  DOI：

  10.1021/ja028043y
• 作为产物：
  描述：

  哌啶酮 在 [(S,S)-(BDPP)Ir(COD)]BF₄ 、 potassium tert-butylate 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 20.0~55.0 ℃ 、448.17 kPa 条件下， 反应 25.5h， 生成 (S)-3-(4-氟苄基)-2-哌啶酮
  参考文献：
  名称：

  Enantioselective Hydrogenation of 3-Alkylidenelactams:  High-Throughput Screening Provides a Surprising Solution

  摘要：

  High-throughput screening of 256 potential catalysts (8 metal precursors x 32 phosphine ligands) has identified [(BDPP)Ir(COD)]BF4 as a catalyst for the enantioselective hydrogenation of 3-alkylidenelactams. This result is surprising given the highly flexible backbone of the BDPP ligand and the ineffectiveness of this catalyst in other applications. The asymmetric hydrogenation appears fairly general for five- and six-membered lactams and in one case has been scaled up to a 20 kg level.

  DOI：

  10.1021/ja028043y

文献信息

• Process for the manufacture of optically active 3-substituted lactams by asymmetric hydrogenation of 3-alkylidenelactams
  申请人：——

  公开号：US20040010139A1

  公开（公告）日：2004-01-15

  The present invention relates generally to processes for the efficient production optically active 3-substituted lactams of formula (I) 1 process, comprising: contacting a compound of formula (II): 2 with hydrogen under a suitable pressure in the presence of an iridium complex of the formula (R 2 )IrL + X − wherein L is a chelating diene, X is a non coordinating anion, and R 2 is selected from 3

  本发明通常涉及一种高效生产光学活性的3-取代内酰胺的方法，其中包括：将式（II）的化合物与氢在适当压力下在(R2)IrL+X−的铱配合物存在下接触，其中L是螯合二烯，X是非配位阴离子，R2是选择自3。
• Stereoselective Process for a CCR3 Antagonist
  作者：Tai-Yuen Yue、Douglas D. McLeod、Kevin B. Albertson、Steven R. Beck、Joerg Deerberg、Joseph M. Fortunak、William A. Nugent、Lilian A. Radesca、Liya Tang、Cathie Dong Xiang

  DOI：10.1021/op050202l

  日期：2006.3.1

  A convergent, multikilogram, stereoselective synthesis of 1 is described. A key fragment, (S)-3-(4-fluorobenzyl)piperidine (2) was synthesized from valerolactam in three steps using our recently discovered Ir-BDPP-catalyzed asymmetric hydrogenation. Another key fragment, (IR,2R)-2-(benzyloxycarbonylamino)cyclohexanecarboxaldehyde (3) was synthesized from meso-hexahydrophthalic anhydride in seven steps. The stereochemistry was set in the first step of this sequence via a quinidine-mediated desymmetrization of the meso-anhydride. Coupling of the fragments 2 and 3 followed by deprotection provided the penultimate 23. The active pharmaceutical ingredient (API) free base I was obtained by treatment of 23 with the aminothiazole fragment 4 under mild conditions.
• US7015320B2
  申请人：——

  公开号：US7015320B2

  公开（公告）日：2006-03-21
• Enantioselective Hydrogenation of 3-Alkylidenelactams:  High-Throughput Screening Provides a Surprising Solution
  作者：Tai-Yuen Yue、William A. Nugent

  DOI：10.1021/ja028043y

  日期：2002.11.1

  High-throughput screening of 256 potential catalysts (8 metal precursors x 32 phosphine ligands) has identified [(BDPP)Ir(COD)]BF4 as a catalyst for the enantioselective hydrogenation of 3-alkylidenelactams. This result is surprising given the highly flexible backbone of the BDPP ligand and the ineffectiveness of this catalyst in other applications. The asymmetric hydrogenation appears fairly general for five- and six-membered lactams and in one case has been scaled up to a 20 kg level.