甲基(1S,3R,4R)-2-氮杂双环[2.2.1]庚烷-3-羧酸酯 | 297143-31-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 甲基(1S,3R,4R)-2-氮杂双环[2.2.1]庚烷-3-羧酸酯
• 中文别名: 2-氮杂双环[2.2.1]庚烷-3-甲酸,甲酯,(1S,3R,4R)
• 英文名称: methyl (1S,3R,4R)-2-azabicyclo[2.2.1]heptane-3-carboxylate
• 英文别名: (1S,3R,4R)-2-azabicyclo[2.2.1]heptane-3-carboxylic acid methyl ester
• CAS: 297143-31-8
• 化学式: C₈H₁₃NO₂
• 分子量: 155.197
• InChiKey: HPVCCAYXVXMOOP-DSYKOEDSSA-N

物化性质

• 沸点：
  215.1±23.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲基(1S,3R,4R)-2-氮杂双环[2.2.1]庚烷-3-羧酸酯 在 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.67h， 生成 methyl (1S,3R,4R)-2-benzyl-3-[hydroxy(phenyl)methyl]-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：

  2-(tert-butyl) 3-methyl (1S,3R,4R)-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 甲基(1S,3R,4R)-2-氮杂双环[2.2.1]庚烷-3-羧酸酯
  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

• Synthesis and evaluation of N,S-compounds as chiral ligands for transfer hydrogenation of acetophenoneElectronic supplementary information (ESI) available: NMR spectra. See http://www.rsc.org/suppdata/ob/b2/b208907f/
  作者：Jenny K. Ekegren、Peter Roth、Klas Källström、Tibor Tarnai、Pher G. Andersson

  DOI：10.1039/b208907f

  日期：2003.1.13

  New nitrogen- and sulfur-containing compounds, bicyclic and monocyclic, were prepared and evaluated as ligands in the transfer hydrogenation of acetophenone. Utilising [Ir(COD)Cl]2 as metal precursor the best result, 80% ee, was obtained using a bicyclic sulfoxide ligand.

  新型含氮和含硫单环及双环化合物被制备并作为配体用于乙酰苯的氢转移反应中评估。使用[Ir(COD)Cl]2作为金属前驱体，通过一种双环亚砜配体获得了最佳结果，即80%的ee（对映体过量）。
• [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。
• A rigid dirhodium(II) carboxylate as an efficient catalyst for the asymmetric cyclopropanation of olefins
  作者：Sophie K Bertilsson、Pher G Andersson

  DOI：10.1016/s0022-328x(00)00025-5

  日期：2000.5

  The dirhodium(II) complex 7 of (1S,3R,4R)-2-(p-tert-butylphenylsulphonyl)-2-aza-bicyclo[2.2.1]heptane-3-carboxylic acid (3) (or its enantiomer) was synthesised in four steps from cyclopentadiene, (R)- or (S)-phenylethylamine and methyl glyoxylate. Complex 7 was evaluated as a catalyst in the asymmetric cyclopropanation of alkenes with vinyl- and phenyl-diazoesters, resulting in enantioselectivity of

  （1 S，3 R，4 R）-2-（对-叔丁基丁基苯磺酰基）-2-氮杂-双环[2.2.1]庚烷-3-羧酸（3）的二价铑（II）配合物7（3）（或它的对映体）是由环戊二烯，（R）-或（S）-苯乙胺和乙醛酸甲酯分四个步骤合成的。在烯烃与乙烯基和苯基重氮酯的不对称环丙烷化反应中，络合物7被评估为催化剂，对映选择性高达92％。
• 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%.
• [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