methyl (1S,3R,4R)-2-benzyl-2-azabicyclo[2.2.1]heptane-3-carboxylate | 251302-01-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: methyl (1S,3R,4R)-2-benzyl-2-azabicyclo[2.2.1]heptane-3-carboxylate
• CAS: 251302-01-9
• 化学式: C₁₅H₁₉NO₂
• 分子量: 245.321
• InChiKey: LLDPTSDUUSECGZ-HZSPNIEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (1S,3R,4R)-2-benzyl-2-azabicyclo[2.2.1]heptane-3-carboxylate 在 lithium diisopropyl amide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以90%的产率得到(1S,3S,4R)-methyl 2-benzyl-2-azabicyclo[2.2.1]heptane-3-carboxylate
  参考文献：
  名称：

  Highly Diastereoselective Reaction of 2-Azanorbornyl Enolates with Electrophiles

  摘要：

  A highly diastereoselective reaction of 2-azanorbornyl enolates with electrophiles has been studied. Deprotonation of 4 with LDA at low temperature affords the corresponding exocyclic lithium enolate 5, which reacts with different electrophiles such as alkyl halides, aldehydes and acyl chlorides to give the corresponding exo addition products 6, The products are formed in good yields and with diastereoselectivities above 95%.

  DOI：

  10.1021/ol990942c
• 作为产物：
  描述：

  methyl (1R,3R,4S)-2-((S)-1-phenylethyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate 在 盐酸 、 氢气 、 palladium(II) hydroxide 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 50.0 ℃ 、344.75 kPa 条件下， 反应 51.0h， 生成 methyl (1S,3R,4R)-2-benzyl-2-azabicyclo[2.2.1]heptane-3-carboxylate
  参考文献：
  名称：

  [EN] INHIBITORS OF PEPTIDYLARGININE DEIMINASES
  [FR] INHIBITEURS DE PEPTIDYLARGININE DÉIMINASES

  摘要：

  本公开涉及用于治疗与肽基精氨酸脱亚胺酶（PADs）相关的疾病（例如肽基精氨酸脱亚胺酶4型（PAD4））的新化合物。本公开还涉及用于制备这些化合物的过程和中间体，使用这些化合物的方法以及包含所述化合物的制药组合物。

  公开号：

  WO2022140390A1

文献信息

• 2-Azanorbornyl Alcohols:  Very Efficient Ligands for Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation of Aromatic Ketones
  作者：Diego A. Alonso、Sofia J. M. Nordin、Peter Roth、Tibor Tarnai、Pher G. Andersson、Marc Thommen、Ulrich Pittelkow

  DOI：10.1021/jo991914a

  日期：2000.5.1

  2-Azanorbornyl-derived amino alcohols were prepared and evaluated as ligands in the Ru(II)-catalyzed asymmetric transfer hydrogenation of aromatic ketones. To improve selectivity and rate, the structure of the ligand was optimized. Acetophenone was reduced using 0.5 mol % catalyst in 40 min in 94% ee. This system was also able to reduce a wide range of aromatic ketones to the corresponding alcohols, while maintaining

  制备了2-氮杂降冰片基衍生的氨基醇，并将其评估为Ru（II）催化的芳族酮的不对称转移氢化中的配体。为了提高选择性和速率，对配体的结构进行了优化。在40分钟内于94％ee中，使用0.5 mol％的催化剂还原苯乙酮。该体系还能够将多种芳族酮还原为相应的醇，同时保持高对映选择性和产率。检查了催化剂负载和反应容器中助溶剂存在的影响，并进行了线性研究。
• [EN] MACROCYCLIC INHIBITORS OF PEPTIDYLARGININE DEIMINASES<br/>[FR] INHIBITEURS MACROCYCLIQUES DE PEPTIDYLARGININE DÉIMINASES
  申请人：GILEAD SCIENCES INC

  公开号：WO2021222353A1

  公开（公告）日：2021-11-04

  The present disclosure relates to novel compounds for use in therapeutic treatement of a disease associated with peptidylarginine deiminases (PADs), such as peptidylarginine deiminase type 4 (PAD4). The present disclosure also relates to processes and intermediates for the preparation of such compounds, methods of using such compounds and pharmaceutical compositions comprising the compounds described herein.

  本公开涉及用于治疗与肽精氨酸脱亚氨酶（PADs）相关的疾病的新化合物，例如肽精氨酸脱亚氨酶类型4（PAD4）。本公开还涉及用于制备这些化合物的过程和中间体，使用这些化合物的方法以及包含所述化合物的药物组合物。
• [EN] INHIBITORS OF PEPTIDYLARGININE DEIMINASES<br/>[FR] INHIBITEURS DE PEPTIDYLARGININE DÉIMINASES
  申请人：GILEAD SCIENCES INC

  公开号：WO2022140428A3

  公开（公告）日：2022-08-04
• Highly Diastereoselective Reaction of 2-Azanorbornyl Enolates with Electrophiles
  作者：Diego A. Alonso、Sofia J. M. Nordin、Pher G. Andersson

  DOI：10.1021/ol990942c

  日期：1999.11.1

  A highly diastereoselective reaction of 2-azanorbornyl enolates with electrophiles has been studied. Deprotonation of 4 with LDA at low temperature affords the corresponding exocyclic lithium enolate 5, which reacts with different electrophiles such as alkyl halides, aldehydes and acyl chlorides to give the corresponding exo addition products 6, The products are formed in good yields and with diastereoselectivities above 95%.