找化学品上960化工网!
960化工网

(4R)-4-[3-(环戊氧基)-4-甲氧基苯基]吡咯-2-酮 | 85416-75-7

(4R)-4-[3-(环戊氧基)-4-甲氧基苯基]吡咯-2-酮
R-(-)-Rolipram
85416-75-7
C16H21NO3
275.342844724655
如需查看该化合物的详细结构式,mol文件,smile,InChi 请点击:(4R)-4-[3-(环戊氧基)-4-甲氧基苯基]吡咯-2-酮结构式
354333406
简介
(R)-(-)-Rolipram是cAMP-特异的PDE4抑制剂,IC50为220nM。在抑制PDE4膜结合实验中其抑制性高于(+)-rolipram 2.5倍。
名称和标识符
MDL MFCD03093860
InChIKey HJORMJIFDVBMOB-LBPRGKRZSA-N
Inchi 1S/C16H21NO3/c1-19-14-7-6-11(12-9-16(18)17-10-12)8-15(14)20-13-4-2-3-5-13/h6-8,12-13H,2-5,9-10H2,1H3,(H,17,18)/t12-/m0/s1
SMILES O(C1CCCC1)C1C=C([C@H]2CC(=O)NC2)C=CC=1OC
别名信息
- 中文别名 -
  • (4R)-4-[3-(环戊氧基)-4-甲氧基苯基]吡咯-2-酮
  • (R)-(-)-咯利普兰
  • (4S)-4-[3-(环戊基氧基)-4-甲氧基苯基]-2-吡咯烷酮
  • 咯利普兰
  • (R)-(-)-4-[3-(环戊氧基)-4-甲氧基苯基]吡咯烷 -2-酮
- 英文别名 -
  • (R)-4-(3-(Cyclopentyloxy)-4-methoxyphenyl)pyrrolidin-2-one
  • (R)-(-)-Rolipram
  • R-(-)-Rolipram
  • (-)-Rolipram
  • (4R)-4-[3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]PYRROLIDIN-2-ONE
  • (R)-Rolipram
  • (S)-ROLIPRAM
  • R-(-)-4-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidinone
  • (R)-(-)-4-[3-(Cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one
  • (4S)-4-[3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]PYRROLIDIN-2-ONE
  • R-Rolipram
  • DPX51KUP08
  • (R)-4-(3-Cyclopentyloxy-4-methoxy-phenyl)-pyrrolidin-2-one
  • C16H21NO3
  • 1xmy
  • Rolipram, (-)-
  • PubChem18284
  • 3g4k
  • 1ro6
  • 1q9m
  • HMS3412I06
  • HMS3676I06
  • HMS3267P19
  • (4R)-4-[3-(Cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidinone (ACI)
  • 2-Pyrrolidinone, 4-[3-(cyclopentyloxy)-4-methoxyphenyl]-, (R)- (ZCI)
  • (4R)-4-(3-Cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-one
  • (4r)-4-[3-(Cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one
物化性质
实验特性
LogP 2.94890
PSA 47.56000
沸点 472.7°C at 760 mmHg
熔点 132.0 to 136.0 deg-C
闪点 239.7 °C
密度 1.155
计算特性
精确分子量 275.15200
氢键供体数量 1
氢键受体数量 3
可旋转化学键数量 4
同位素质量 275.152
重原子数量 20
复杂度 341
同位素原子数量 0
确定原子立构中心数量 1
不确定原子立构中心数量 0
确定化学键立构中心数量 0
不确定化学键立构中心数量 0
共价键单元数量 1
拓扑分子极性表面积 47.6
海关数据
海关编码 2933790090
海关数据

中国海关编码:

2933790090

概述:

2933790090 其他内酰胺. 增值税率:17.0% 退税率:9.0% 监管条件:无 最惠国关税:9.0% 普通关税:20.0%

申报要素:

品名, 成分含量, 用途, 乌洛托品请注明外观, 6-己内酰胺请注明外观, 签约日期

Summary:

2933790090. other lactams. VAT:17.0%. Tax rebate rate:9.0%. . MFN tariff:9.0%. General tariff:20.0%

合成路线

合成路线:1 步

反应条件:
参考文献:
Chiral synthesis of phosphodiesterase inhibitor, (R)-(-)-rolipram, by means of enantioselective deprotonation strategy
Honda, Toshio; et al, Heterocycles, 1996, 42(1), 109-12

合成路线:1 步

反应条件:
参考文献:
Catalytic, asymmetric azidations at carbonyls: achiral and meso-anhydride desymmetrisation affords enantioenriched γ-lactams
Smith, Simon N.; et al, Organic & Biomolecular Chemistry, 2022, 20(32), 6384-6393

合成路线:1 步

反应条件:
参考文献:
Enantioselective syntheses of (-)-(R)-rolipram, (-)-(R)-baclofen and other GABA analogues via rhodium-catalyzed conjugate addition of arylboronic acids
Becht, Jean-Michel; et al, Synthesis, 2003, (18), 2805-2810

合成路线:1 步

反应条件:
参考文献:
Development of a Catalytic Enantioselective Conjugate Addition of 1,3-Dicarbonyl Compounds to Nitroalkenes for the Synthesis of Endothelin-A Antagonist ABT-546. Scope, Mechanism, and Further Application to the Synthesis of the Antidepressant Rolipram
Barnes, David M.; et al, Journal of the American Chemical Society, 2002, 124(44), 13097-13105

合成路线:1 步

反应条件:
参考文献:
Catalytic enantioselective synthesis of the phosphodiesterase type IV inhibitor (R)-(-)-rolipram via intramolecular C-H insertion process
Anada, Masahiro; et al, Synlett, 1999, (11), 1775-1777

合成路线:1 步

反应条件:
参考文献:
Practical large-scale preparation of (R)-rolipram using chiral nickel catalyst
Wen, Lixin; et al, Synthetic Communications, 2012, 42(22), 3288-3295

合成路线:1 步

反应条件:
参考文献:
Synthesis and evaluation of N-aryl pyrrolidinones as novel anti-HIV-1 agents. Part 1
Wu, Baogen; et al, Bioorganic & Medicinal Chemistry Letters, 2006, 16(13), 3430-3433

合成路线:1 步

反应条件:
参考文献:
Rh-Catalyzed Asymmetric Hydrogenation of γ-Phthalimido-Substituted α,β-Unsaturated Carboxylic Acid Esters: An Efficient Enantioselective Synthesis of β-Aryl-γ-amino Acids
Deng, Jun; et al, Organic Letters, 2007, 9(23), 4825-4828

合成路线:2 步

反应条件:
参考文献:
Practical large-scale preparation of (R)-rolipram using chiral nickel catalyst
Wen, Lixin; et al, Synthetic Communications, 2012, 42(22), 3288-3295

合成路线:1 步

反应条件:
参考文献:
Method for synthesizing (R)-rolipram
, China, , ,

合成路线:1 步

反应条件:
参考文献:
Efficient synthesis of (-)-(R)- and (+)-(S)-rolipram
Kaur, Ramandeep; et al, Tetrahedron Letters, 2017, 58(46), 4333-4335

合成路线:1 步

反应条件:
参考文献:
Highly Enantioselective Synthesis of Chiral γ-Lactams by Rh-Catalyzed Asymmetric Hydrogenation
Lang, Qiwei; et al, ACS Catalysis, 2018, 8(6), 4824-4828

合成路线:1 步

参考文献:
Crystal structure, absolute configuration, and phosphodiesterase inhibitory activity of (+)-1-(4-bromobenzyl)-4-[(3-cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidinone
Baures, Paul W.; et al, Journal of Medicinal Chemistry, 1993, 36(22), 3274-7

合成路线:1 步

反应条件:
参考文献:
Synthesis of β-substituted γ-aminobutyric acid derivatives through enantioselective photoredox catalysis
Ma, Jiajia; et al, Angewandte Chemie, 2018, 57(35), 11193-11197

合成路线:1 步

反应条件:
参考文献:
Co-catalyzed reductive cyclization of azido and cyano substituted α,β-unsaturated esters with NaBH4: enantioselective synthesis of (R)-baclofen and (R)-rolipram
Paraskar, Abhimanyu S.; et al, Tetrahedron, 2006, 62(20), 4907-4916
相关文献
专业数据库参考
PubChemId 354333406
参考资料
Reaxys RN 5442919
Beilstein R160943
您可能关注
(4R)-4-[3-(环戊氧基)-4-甲氧基苯基]吡咯-2-酮推荐生产厂家
960化工网为您提供(4R)-4-[3-(环戊氧基)-4-甲氧基苯基]吡咯-2-酮专业化合物百科信息,包括中文名,英文名,分子式,分子量,以及该化合物的CasNo.:85416-75-7,和相关理化性质;并提供了优质生产厂家信息包括厂家名称和联系方式等;| WAP 版:85416-75-7
平台客服 平台客服

平台在线客服