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(5S)-5-[(p-toluenesulfonyl)methyl]-2-pyrrolidinone | 288387-56-4

中文名称
——
中文别名
——
英文名称
(5S)-5-[(p-toluenesulfonyl)methyl]-2-pyrrolidinone
英文别名
(S)-5-(tosylmethyl)pyrrolidin-2-one;(5S)-5-(p-Toluenesulphonylmethyl)-2-pyrrolidinone;(5S)-5-[(4-methylphenyl)sulfonylmethyl]pyrrolidin-2-one
(5S)-5-[(p-toluenesulfonyl)methyl]-2-pyrrolidinone化学式
CAS
288387-56-4
化学式
C12H15NO3S
mdl
——
分子量
253.322
InChiKey
GJHFDMMDRCOQKN-JTQLQIEISA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    528.5±42.0 °C(Predicted)
  • 密度:
    1.237±0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    1
  • 重原子数:
    17
  • 可旋转键数:
    3
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.42
  • 拓扑面积:
    71.6
  • 氢给体数:
    1
  • 氢受体数:
    3

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
    —— (S)-5-(p-tolylthiomethyl)pyrrolidin-2-one 388574-14-9 C12H15NOS 221.323
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量
    —— (8R,8aS)-8-(p-toluenesulfonyl)perhydro-3-indolizidinone 334999-99-4 C15H19NO3S 293.387
    —— (9R,9aS)-9-(p-toluenesulfonyl)-2,3,5,8,9,9a-hexahydro-1H-pyrrolo[1,2-a]azepin-3-one —— C16H19NO3S 305.398
    —— (4S,8R,8aS)-6-Methylene-8-(toluene-4-sulfonyl)-hexahydro-indolizin-3-one —— C16H19NO3S 305.398
    —— (8S,8aS)-8-(p-toluenesulfonyl)perhydro-3,7-indolizidinedione —— C15H17NO4S 307.37
    —— (4S,5S,8S,8aS)-5-Methyl-8-(toluene-4-sulfonyl)-hexahydro-indolizine-3,7-dione —— C16H19NO4S 321.397
    —— (6R,8S,8aS)-6-methyl-8-(p-toluenesulfonyl)perhydro-3,7-indolizidinedione —— C16H19NO4S 321.397
    —— (6S,8S,8aS)-6-methyl-8-(p-toluenesulfonyl)perhydro-3,7-indolizidinedione —— C16H19NO4S 321.397

反应信息

  • 作为反应物:
    描述:
    (5S)-5-[(p-toluenesulfonyl)methyl]-2-pyrrolidinonedisodium hydrogenphosphate 、 sodium amalgam 、 lithium aluminium tetrahydride 、 sodium hydride 作用下, 以 甲醇乙醚N,N-二甲基甲酰胺 为溶剂, 反应 76.0h, 生成 (-)-(8aR)-octahydroindolizine
    参考文献:
    名称:
    Convergent asymmetric synthesis of indolizidines from (S)-5-(tosylmethyl)-2-pyrrolidinone: synthesis of (−)-δ-coniceine
    摘要:
    The enantiomerically pure (S)-5-(tosylmethyl)-2-pyrrolidinone 2, prepared from commercially available (S)-pyroglutaminol, is dialkylated at the nitrogen atom and the cc-sulfonyl position using several dielectrophiles using sodium hydride as the base to diastereoselectively afford indolizidine derivatives 5 and the less common hexahydropyrrolo[1,2-a]azepin-3-one 6 in moderate to good yield. This domino process has been applied to the synthesis of (-)-delta -coniceine. (C) 2001 Elsevier Science Ltd. All rights reserved.
    DOI:
    10.1016/s0957-4166(01)00377-9
  • 作为产物:
    参考文献:
    名称:
    Convergent asymmetric synthesis of indolizidines from (S)-5-(tosylmethyl)-2-pyrrolidinone: synthesis of (−)-δ-coniceine
    摘要:
    The enantiomerically pure (S)-5-(tosylmethyl)-2-pyrrolidinone 2, prepared from commercially available (S)-pyroglutaminol, is dialkylated at the nitrogen atom and the cc-sulfonyl position using several dielectrophiles using sodium hydride as the base to diastereoselectively afford indolizidine derivatives 5 and the less common hexahydropyrrolo[1,2-a]azepin-3-one 6 in moderate to good yield. This domino process has been applied to the synthesis of (-)-delta -coniceine. (C) 2001 Elsevier Science Ltd. All rights reserved.
    DOI:
    10.1016/s0957-4166(01)00377-9
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文献信息

  • Asymmetric cross-benzoin condensation promoted by a chiral triazolium precatalyst bearing a pyridine moiety
    作者:Takahiro Soeta、So Mizuno、Yuichi Hatanaka、Yutaka Ukaji
    DOI:10.1016/j.tet.2017.05.001
    日期:2017.6
    Cross-benzoin condensation catalyzed by NHC, prepared from chiral triazolium salts bearing a pyridine ring, afforded α-hydroxy ketones with reasonable chemical yields and enantioselectivities. A wide range of aliphatic and aromatic aldehydes were successfully used in the reaction.
    由带有吡啶环的手性三唑鎓盐制备的NHC催化的交叉安息香缩合反应可制得具有合理化学收率和对映选择性的α-羟基酮。反应中成功使用了多种脂族和芳族醛。
  • Quinazoline derivatives as angiogenesis inhibitors
    申请人:Stokes SE Elaine
    公开号:US20060004017A1
    公开(公告)日:2006-01-05
    The invention relates to the use of compounds of formula (I), wherein ring C is an 8, 9, 10, 12 or 13-membered bicyclic or tricyclic moiety which optionally may contain 1-3 heteroatoms selected independently from O, N and S; Z is —O—, —NH—, —S—, —CH 2 — or a direct bond; n is 0-5; m is 0-3; R 2 represents hydrogen, hydroxy, halogeno, cyano, nitro, trifluoromethyl, C 1-3 alkyl, C 1-3 alkoxy, C 1-3 alkylsulphanyl, —NR 3 R 4 (wherein R 3 and R 4 , which may be the same or different, each represents hydrogen or C 1-3 alkyl), or R 5 X t — (wherein X 1 and R 5 are as defined herein; R 1 represents hydrogen, oxo, halogeno, hydroxy, C 1-4 alkoxy, C 1-4 alkyl, C 1-4 alkoxymethyl, C 1-4 alkanoyl, C 1-4 haloalkyl, cyano, amino, C 2-5 alkenyl, C 2-5 alkynyl, C 1-3 alkanoyloxy, nitro, C 1-4 alkanoylamino, C 1-4 alkoxycarbonyl, C 1-4 alkylsulphanyl, C 1-4 alkylsulphinyl, C 1-4 alkylsulphonyl, carbamoyl, N —C 1-4 alkylcarbamoyl, N,N -di(C 1-4 alkyl)carbamoyl, aminosulphonyl, N —C 1-4 alkylaminosulphonyl, N,N -di(C 1-4 alkyl)aminosulphonyl, N -(C 1-4 alkylsulphonyl)amino, N —(C 1-4 alkylsulphonyl)— N —(C 1-4 alkyl)amino, N,N -di(C 1-4 alkylsulphonyl)amino, a C 3-7 alkylene chain joined to two ring C carbon atoms, C 1-4 alkanoylaminoC 1-4 alkyl, carboxy or a group R 56 X 10 (wherein X 10 and R 56 are as defined herein); and salts thereof, in the manufacture of a medicament for use in the production of an antiangiogenic and/or vascular permeability reducing effect in warm-blooded animals, processes for the preparation of such compounds, pharmaceutical compositions containing a compound of formula (I) or a pharmaceutically acceptable salt thereof as active ingredient and compounds of formula (I). The compounds of formula (I) and the pharmaceutically acceptable salts thereof inhibit the effects of VEGF, a property of value in the treatment of a number of disease states including cancer and rheumatoid arthritis.
    本发明涉及使用公式(I)的化合物,其中环C是一个包含1-3个独立选择的杂原子O、N和S的8、9、10、12或13元双环或三环基团;Z是-O-、-NH-、-S-、-CH2-或直接键;n为0-5;m为0-3;R2表示氢、羟基、卤代、氰基、硝基、三氟甲基、C1-3烷基、C1-3烷氧基、C1-3烷基硫基、-NR3R4(其中R3和R4,可以相同,也可以不同,分别表示氢或C1-3烷基),或R5Xt-(其中X1和R5如上定义);R1表示氢、酮、卤代、羟基、C1-4烷氧基、C1-4烷基、C1-4烷氧甲基、C1-4酰基、C1-4卤代烷基、氰基、氨基、C2-5烯基、C2-5炔基、C1-3酰氧基、硝基、C1-4酰胺基、C1-4烷氧羰基、C1-4烷基硫基、C1-4烷基亚硫基、C1-4烷基磺酰基、氨基甲酰基、N-C1-4烷基氨基甲酰基、N,N-二(C1-4烷基)氨基甲酰基、氨基磺酰基、N-C1-4烷基氨基磺酰基、N,N-二(C1-4烷基)氨基磺酰基、N-(C1-4烷基磺酰基)氨基、N-(C1-4烷基磺酰基)-N-(C1-4烷基)氨基、N,N-二(C1-4烷基磺酰基)氨基、连接两个环C碳原子的C3-7烷基链、C1-4酰胺基C1-4烷基、羧基或R56X10基团(其中X10和R56如上定义);以及其盐,在制造用于产生在温血动物中的抗血管生成和/或血管通透性减少效应的药物中使用,制备这种化合物的方法,含有公式(I)的化合物或其药学上可接受的盐作为活性成分的制药组合物和公式(I)的化合物。公式(I)的化合物及其药学上可接受的盐抑制VEGF的效果,在治疗包括癌症和类风湿性关节炎在内的多种疾病状态中具有价值。
  • Quinazoline Derivatives as Angiogenesis Inhibitors
    申请人:Stokes Elaine S.E.
    公开号:US20120197027A1
    公开(公告)日:2012-08-02
    The invention relates to the use of compounds of formula (I) and salts thereof, in the manufacture of a medicament for use in the production of an antiangiogenic and/or vascular permeability reducing effect in warm-blooded animals, processes for the preparation of such compounds, pharmaceutical compositions containing a compound of formula I or a pharmaceutically acceptable salt thereof as active ingredient and compounds of formula I. The compounds of formula I and the pharmaceutically acceptable salts thereof inhibit the effects of VEGF, a property of value in the treatment of a number of disease states including cancer and rheumatoid arthritis.
    该发明涉及使用式(I)的化合物及其盐,在制造用于在温血动物中产生抗血管生成和/或减少血管通透性效果的药物中的应用,制备这种化合物的方法,含有式I的化合物或其药学上可接受的盐作为活性成分的药物组合物以及式I的化合物。式(I)的化合物及其药学上可接受的盐抑制VEGF的效果,这是在治疗包括癌症和类风湿性关节炎在内的多种疾病状态中具有价值的特性。
  • Polynucleotide assay reagent and method
    申请人:ANTIVIRALS INC.
    公开号:EP0639582A2
    公开(公告)日:1995-02-22
    The invention provides a use of a morpholino subunit of the formula (I) where P is a purine or pyrimidine base-pairing moiety, and T is H or an N-protective group, for the production of a polymer capable of hydrogen-bonding to complementary bases in a polynucleotide, where in said polymer (i) the subunits are joined predominantly by substantially uncharged, achiral linkages, and (ii) each linkage joins the morpholino nitrogen of one subunit to the 5' exocyclic carbon of an adjacent subunit.
    本发明提供了式 (I) 吗啉亚基的用途 其中 P 是嘌呤或嘧啶碱基配对分子,T 是 H 或 N 保护基团,用于生产能够与多核苷酸中的互补碱基发生氢键连接的聚合物,在所述聚合物中,(i) 亚基主要通过基本上不带电的非手性连接物连接,(ii) 每个连接物将一个亚基的吗啉基氮连接到相邻亚基的 5'外环碳上。
  • QUINAZOLINE DERIVATIVES AS ANGIOGENESIS INHIBITORS AND INTERMEDIATES THEREFORE
    申请人:AstraZeneca AB
    公开号:EP1553097A1
    公开(公告)日:2005-07-13
    The invention relates to the use of compounds of the formula I: wherein ring C is an 8, 9, 10, 12 or 13-membered bicyclic or tricyclic moiety which optionally may contain 1-3 heteroatoms selected independently from O, N and S; Z is -O-, -NH-, -S-, -CH2- or a direct bond; n is 0-5; m is 0-3; R2 represents hydrogen, hydroxy, halogeno, cyano, nitro, trifluoromethyl, C1-3alkyl, C1-3alkoxy, C1-3alkylsulphanyl, -NR3R4 (wherein R3 and R4, which may be the same or different, each represents hydrogen or C1-3alkyl), or R5X1- (wherein X1 and R5 are as defined herein; R1 represents hydrogen, oxo, halogeno, hydroxy, C1-4alkoxy, C1-4alkyl, C1-4alkoxymethyl, C1-4alkanoyl, C1-4haloalkyl, cyano, amino, C2-5alkenyl, C2-5alkynyl, C1-3alkanoyloxy, nitro, C1-4alkanoylamino, C1-4alkoxycarbonyl, C1-4alkylsulphanyl, C1-4alkylsulphinyl, C1-4alkylsulphonyl, carbamoyl, N-C1-4alkylcarbamoyl, N,N-di(C1-4alkyl)carbamoyl, aminosulphonyl, N-C1-4alkylaminosulphonyl, N,N-di(C1-4alkyl)aminosulphonyl, N-(C1-4alkylsulphonyl)amino, N-(C1-4alkylsulphonyl)-N-(C1-4alkyl)amino, N,N-di(C1-4alkylsulphonyl)amino, a C3-7alkylene chain joined to two ring C carbon atoms, C1-4alkanoylaminoC1-4alkyl, carboxy or a group R56X10 (wherein X10 and R56 are as defined herein); and salts thereof, in the manufacture of a medicament for use in the production of an antiangiogenic and/or vascular permeability reducing effect in warm-blooded animals, processes for the preparation of such compounds, pharmaceutical compositions containing a compound of formula I or a pharmaceutically acceptable salt thereof as active ingredient and compounds of formula I. The compounds of formula I and the pharmaceutically acceptable salts thereof inhibit the effects of VEGF, a property of value in the treatment of a number of disease states including cancer and rheumatoid arthritis.
    本发明涉及式 I 化合物的用途: 其中环 C 是 8、9、10、12 或 13 元双环或三环分子,可任选含有 1-3 个独立选自 O、N 和 S 的杂原子;Z 是 -O-、-NH-、-S-、-CH2- 或直接键;n 是 0-5;m 是 0-3;R2 代表氢、羟基、卤代、氰基、硝基、三氟甲基、C1-3 烷基、C1-3 烷氧基、C1-3 烷基硫代、-NR3R4(其中 R3 和 R4 可以相同或不同,各自代表氢或 C1-3 烷基)或 R5X1-(其中 X1 和 R5 如本文所定义;R1代表氢、氧代、卤代、羟基、C1-4烷氧基、C1-4烷基、C1-4烷氧基甲基、C1-4烷酰基、C1-4卤代烷基、氰基、氨基、C2-5烯基、C2-5炔基、C1-3烷酰氧基硝基、C1-4-烷酰氨基、C1-4-烷氧基羰基、C1-4-烷基硫酰基、C1-4-烷基亚砜基、C1-4-烷基磺酰基、氨基甲酰基、N-C1-4-烷基氨基甲酰基、N,N-二(C1-4-烷基)氨基甲酰基氨基磺酰基、N-C1-4烷基氨基磺酰基、N,N-二(C1-4烷基)氨基磺酰基、N-(C1-4烷基磺酰基)氨基、N-(C1-4烷基磺酰基)-N-(C1-4烷基)氨基、N,N-二(C1-4烷基磺酰基)氨基、与两个环 C 碳原子相连的 C3-7 烯链、C1-4-烷酰氨基 C1-4烷基、羧基或基团 R56X10(其中 X10 和 R56 如本文所定义);及其盐,用于制造在温血动物中产生抗血管生成和/或降低血管通透性作用的药物、制备此类化合物的工艺、含有式 I 化合物或其药学上可接受的盐作为活性成分的药物组合物以及式 I 化合物。式 I 化合物及其药学上可接受的盐可抑制血管内皮生长因子的作用,这一特性在治疗包括癌症和类风湿性关节炎在内的多种疾病中具有重要价值。
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