methyl (1R,3R,4S)-2-((S)-1-phenylethyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate | 130195-74-3

• 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
• 英文名称: methyl (1R,3R,4S)-2-((S)-1-phenylethyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate
• 英文别名: (1R,3R,4S)-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylic acid methyl ester；methyl (1R,3R,4S)-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate
• CAS: 130195-74-3
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: PWUWUKQPSOGOPL-PMOUVXMZSA-N

物化性质

• 沸点：
  340.9±30.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 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 (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
• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 在 molecular sieve 、 三氟化硼乙醚 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.5h， 生成 methyl (1R,3R,4S)-2-((S)-1-phenylethyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate
  参考文献：
  名称：

  Asymmetric aza-diels-alder reaction using the chiral 1-phenyl ethyl imine of methyl glyoxylate

  摘要：

  DOI：

  10.1016/0040-4039(90)80136-a

文献信息

• [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] POLYCYCLIC-CARBAMOYLPYRIDONE COMPOUNDS AND THEIR USE FOR THE TREATMENT OF HIV INFECTIONS<br/>[FR] COMPOSÉS DE CARBAMOYLPYRIDONE POLYCYCLIQUE ET LEUR UTILISATION POUR LE TRAITEMENT DES INFECTIONS À VIH
  申请人：GILEAD SCIENCES INC

  公开号：WO2015006731A1

  公开（公告）日：2015-01-15

  Compounds for use in the treatment of human immunodeficiency virus (HIV) infection are disclosed. The compounds have the following Formula (I): including stereoisomers and pharmaceutically acceptable salts thereof, wherein R1, X, Y1, Y2, or L are as defined herein. Methods associated with preparation and use of such compounds, as well as pharmaceutical compositions comprising such compounds, are also disclosed.

  用于治疗人类免疫缺陷病毒（HIV）感染的化合物被披露。这些化合物具有以下通式（I）：包括立体异构体及其药学上可接受的盐，其中R1、X、Y1、Y2或L如本文所定义。还披露了与这些化合物的制备和使用相关的方法，以及包含这些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％。
• Polycyclic-carbamoylpyridone compounds and their pharmaceutical use
  申请人：Gilead Sciences, Inc.

  公开号：US10668064B2

  公开（公告）日：2020-06-02

  Compounds for use in the treatment of human immunodeficiency virus (HIV) infection are disclosed. The compounds have the following Formula (I): including stereoisomers and pharmaceutically acceptable salts thereof, wherein R1, X, Y1, Y2, or L are as defined herein. Methods associated with preparation and use of such compounds, as well as pharmaceutical compositions comprising such compounds, are also disclosed.

  本研究公开了用于治疗人类免疫缺陷病毒（HIV）感染的化合物。这些化合物具有下式 (I)： 包括其立体异构体和药学上可接受的盐类，其中 R1、X、Y1、Y2 或 L 如本文所定义。此外，还公开了与制备和使用此类化合物相关的方法，以及包含此类化合物的药物组合物。
• Remote Dipole Effects as a Means to Accelerate [Ru(amino alcohol)]-Catalyzed Transfer Hydrogenation of Ketones
  作者：Sofia J. M. Nordin、Peter Roth、Tibor Tarnai、Diego A. Alonso、Peter Brandt、Pher G. Andersson

  DOI：10.1002/1521-3765(20010401)7:7<1431::aid-chem1431>3.0.co;2-l

  日期：2001.4.1

  A new generation of 2-azanolbornyl amino alcohol ligands for the catalytic transfer hydrogenation reaction of aromatic ketones was synthesized. Extremely active catalysts were formed by introducing a ketal functionality at the I car end of the ligand, Acetophenone was reduced in 96% cc at low catalyst loading, substrate: to catalyst ratio, S/C 5000, within 90 minutes with isopropyl alcohol as the hydrogen donor. It was round that the dioxolane substituent in the ligand increased the turnover frequency, TOF50 from 1050 h(-1) to 3000 h(-1) at an S/C ratio of 1000, Introduction of a methyl group at the carbinol carbon resulted in TOF50 as high as 8500 h(-1), Transfer hydrogenation of a range of aromatic ketones was evaluated and found to reach completion within 30 minutes at room temperature, and excellent enantioselectivity, up to 99% cc, was obtained. A possible explanation for the enhanced activity was provided by density functional calculations, which showed that the presence of a remote dipole in the ligand lowered the transition state energy.