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(S)-4-苄基-3-(5-溴戊基)噁唑烷-2-酮 | 156699-37-5

中文名称
(S)-4-苄基-3-(5-溴戊基)噁唑烷-2-酮
中文别名
(S)-4-苄基-3-(5-溴戊基)恶唑烷-2-酮
英文名称
(S)-4-benzyl-3-(5-bromopentanoyl)oxazolidine-2-one
英文别名
(S)-3-(5-bromopentanoyl)-4-benzyloxazolidin-2-one;(4S)-3-(5-bromovaleryl)-4-phenylmethyl-2-oxazolidinone;2-Oxazolidinone, 3-(5-bromo-1-oxopentyl)-4-(phenylmethyl)-, (4S)-;(4S)-4-benzyl-3-(5-bromopentanoyl)-1,3-oxazolidin-2-one
(S)-4-苄基-3-(5-溴戊基)噁唑烷-2-酮化学式
CAS
156699-37-5
化学式
C15H18BrNO3
mdl
——
分子量
340.217
InChiKey
LRQYSKNJBAVITI-ZDUSSCGKSA-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

  • 熔点:
    68.4 °C
  • 沸点:
    478.7±28.0 °C(Predicted)
  • 密度:
    1.420±0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    3.1
  • 重原子数:
    20
  • 可旋转键数:
    6
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.47
  • 拓扑面积:
    46.6
  • 氢给体数:
    0
  • 氢受体数:
    3

安全信息

  • 储存条件:
    室温

SDS

SDS:f496153baa1a46f3c9b36c90f0bfdb66
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上下游信息

  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    参考文献:
    名称:
    Asymmetric synthesis of ω-bromo-2(S)-azido acids as precursors for the synthesis of novel amino acids
    摘要:
    A series of omega-bromo-2(S)-azido acids with side-chain lengths ranging from 3-5 methylene units has been synthesized. These intermediates enable the facile synthesis of chiral non-natural amino acids containing virtually any nucleophile capable of substituting the omega-bromo group. (C) 1998 Elsevier Science Ltd. All rights reserved.
    DOI:
    10.1016/s0040-4039(97)10608-6
  • 作为产物:
    描述:
    参考文献:
    名称:
    Conjugates of Modified Cryptophycins and RGD-Peptides Enter Target Cells by Endocytosis
    摘要:
    Tumor targeting anticancer drug conjugates that contain a tumor recognition motif (homing device) are of high current relevance. Cryptophycins, naturally occurring cytotoxic cyclo-depsipeptides, have been modified by total synthesis to provide analogues suitable for conjugation to peptide-based homing devices. An array of functionalized beta(2)-amino acids was synthesized and incorporated into cryptophycins. All analogues proved to be highly active in the cytotoxicity assay using the human cervix carcinoma cell line KB-3-1 and its multidrug-resistant subclone KB-V1. Conformational analysis of cryptophycin-52 and two synthetic analogues was performed by NMR and MD methods to obtain information on the influence of the unit C configuration on the overall conformation. An azide-functionalized cryptophycin was connected by CuAAC to an alkyne-containing fluorescently labeled cyclic RGD-peptide as the homing device for internalization studies. Confocal fluorescence microscopy proved integrin-mediated internalization by endocytosis and final lysosomal localization of the cryptophycin prodrug.
    DOI:
    10.1021/jm301346z
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文献信息

  • [EN] FUROPYRIDINE COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS DE FUROPYRIDINE ET SES UTILISATIONS
    申请人:NOVARTIS AG
    公开号:WO2011131709A1
    公开(公告)日:2011-10-27
    The present invention provides a compound of formula (I); a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.
    本发明提供了一种式(I)的化合物;一种用于制造本发明化合物的方法,以及其治疗用途。本发明还提供了药理活性剂的组合和药物组合物。
  • Asymmetric Synthesis of ω‐Bromo‐2(S)‐Methyl Acids as Precursors for Novel Arginine, Lysine, and Mercapto Residues
    作者:M. Kyle Hadden、Kyle P. Kokko、Thomas A. Dix
    DOI:10.1081/scc-200061668
    日期:2005.6.1
    Abstract A series of ω‐bromo‐2(S)‐methyl acids has been synthesized as precursors of novel arginine (Arg), lysine (Lys), and mercapto analogues. These intermediates contain α‐methyl groups and are designed to mask the N‐terminal amine when incorporated in pharmaceutically relevant peptides.
    摘要 已经合成了一系列 ω-溴-2(S)-甲基酸作为新型精氨酸 (Arg)、赖氨酸 (Lys) 和巯基类似物的前体。这些中间体含有 α-甲基,当掺入药物相关的肽中时,它们旨在掩盖 N 端胺。
  • Stereochemical Definition and Chirospecific Synthesis of the Peptide Deformylase Inhibitor Sch 382583
    作者:Reed A. Coats、Sheng-Lian Lee、Kari A. Davis、Kanu M. Patel、Elaine K. Rhoads、Michael H. Howard
    DOI:10.1021/jo035667t
    日期:2004.3.1
    The recently reported natural product Sch 382583 (1), an inhibitor of peptide deformylase, has been synthesized in 16 steps from commercially available starting materials. The three chiral centers were set by a combination of chiral auxiliary and chiral pool approaches. The succinate 5 and piperazic acid 9 moieties were obtained by Evans oxazolidinone imide enolate alkylation and hydrazination/cyclization
    最近报道的天然产物Sch 382583(1),一种肽去甲酰基酶的抑制剂,已由市售起始原料分16步合成。三个手性中心是通过手性辅助方法和手性池方法的组合设置的。分别通过伊文思恶唑烷酮酰亚胺烯酸酯烷基化和酰化/环化获得琥珀酸酯5和哌嗪酸9部分,并且通过格氏(Grignard)取代衍生自I的Weinreb酰胺制备氨基己酮侧链13。-缬氨酸。与所报告的天然产物的数据相比,所得合成材料的光谱数据确定了先前未分配的缬氨酸酮立体中心(C-4)具有S-构型。
  • Enantioselective synthesis of (3R)- and (3S)-piperazic acids. The comparative unimportance of DMPU mediated retro-hydrazination
    作者:Karl J Hale、Jiaqiang Cai、Vern Delisser、Soraya Manaviazar、S.Andrew Peak、Gurpreet S Bhatia、Timothy C Collins、Neha Jogiya
    DOI:10.1016/0040-4020(95)00938-8
    日期:1996.1
    and Manaviazar (1992) on the asymmetric synthesis of (3R)- and (3S)-piperazic acids has been reinvestigated, and the originally claimed product yields fully substantiated. The claims made in reference 13 about the proportions of cyclised product 6 and starting bromide 20 isolated from the low temperature electrophilic hydrazination-nucleophilic cyclisation of 20 with di-t-butylazodicarboxylate (DBAD)
    为了回应Decicco和Leathers的最新文献报告(参考文献13),Hale,Delisser和Manaviazar(1992)关于(3 R)-和(3 S)-哌嗪酸的不对称合成的工作已被重新研究。 ,并且最初要求保护的产品的产量得到了充分证实。参考文献13约环化产物的比例制得的权利要求6和起始溴化物20从低温电hydrazination亲核环化分离20与二吨偶氮二羧酸丁酯(DBAD)和DMPU作为添加剂不准确。他们证明,当将DMPU加入到肼化反应混合物中时,逆酰肼化反应是有问题的,已经证明对环化产物的收率没有严重的不利影响并且是不重要的。参考文献13的另一主要主张是,当使用n -Bu 4 NI代替添加剂(代替DMPU)时,20的亲电肼化和亲核环化产生91%的分离产率中的6,这也是错误的。我们仔细地重复了按比例缩小版本的n -Bu 4 NI催化程序(参考资料13),发现经快速色谱分离后,
  • Azinothricin synthetic studies. 1. Efficient asymmetric synthesis of (3R)- and (3S)-piperazic acids
    作者:Karl J. Hale、Vern M. Delisser、Soraya Manaviazar
    DOI:10.1016/s0040-4039(00)60838-9
    日期:——
    A convenient asymmetric synthesis of both (3R)- and (3S)-piperazic acids has been developed that is based on electrophilic hydrazination of a chiral bromovaleryl carboximide enolate with di-tert-butyl azodicarboxylate, followed by subsequent intramolecular SN2 displacement of the bromide by the resulting substituted aza anion. The diastereoselectivity of the process is typically greater than 96%.
    已经开发了一种方便的不对称合成(3R)-和(3S)-哌嗪酸的方法,该方法基于手性溴丙二酰羧酰亚胺烯醇酸酯与偶氮二叔丁基二羧酸叔丁酯的亲电子酰化作用,随后分子内S N 2置换溴化后得到的取代的氮杂阴离子。该方法的非对映选择性通常大于96%。
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同类化合物

(R)-4-异丙基-2-恶唑烷硫酮 麻黄恶碱 顺-八氢-2H-苯并咪唑-2-酮 顺-1-(4-氟苯基)-4-[1-(4-氟苯基)-4-羰基-1,3,8-三氮杂螺[4.5]癸-8-基]环己甲腈 非达司他 降冰片烯缩醛3-((1S,2S,4S)-双环[2.2.1]庚-5-烯-2-羰基)恶唑烷-2-酮 阿齐利特 阿那昔酮 阿洛双酮 阿帕鲁胺 阿帕他胺杂质2 铟烷-2-YL-甲基胺盐酸 钠2-{[4,5-二羟基-3-(羟基甲基)-2-氧代-1-咪唑烷基]甲氧基}乙烷磺酸酯 重氮烷基脲 詹氏催化剂 解草恶唑 解草噁唑 表告依春 螺莫司汀 螺立林 螺海因氮丙啶 螺[1-氮杂双环[2.2.2]辛烷-8,5'-咪唑烷]-2',4'-二酮 苯甲酸,4-氟-,2-[5,7-二(三氟甲基)-1,8-二氮杂萘-2-基]-2-甲基酰肼 苯氰二硫酸,1-氰基-1-甲基-4-氧代-4-(2-硫代-3-噻唑烷基)丁酯 苯妥英钠杂质8 苯妥英-D10 苯妥英 苯基硫代海因半胱氨酸钠盐 苯基硫代乙内酰脲-谷氨酸 苯基硫代乙内酰脲-蛋氨酸 苯基硫代乙内酰脲-苯丙氨酸 苯基硫代乙内酰脲-色氨酸 苯基硫代乙内酰脲-脯氨酸 苯基硫代乙内酰脲-缬氨酸 苯基硫代乙内酰脲-异亮氨酸 苯基硫代乙内酰脲-天冬氨酸 苯基硫代乙内酰脲-亮氨酸 苯基硫代乙内酰脲-丙氨酸 苯基硫代乙内酰脲-D-苏氨酸 苯基硫代乙内酰脲-(NΕ-苯基硫代氨基甲酰)-赖氨酸 苯基乙内酰脲-甘氨酸 苏氨酸-1-(苯基硫基)-2,4-咪唑烷二酮(1:1) 色氨酸标准品002 膦酸,(2-羰基-1-咪唑烷基)-,二(1-甲基乙基)酯 脱氢-1,3-二甲基尿囊素 聚(d(A-T)铯) 羟甲基-5,5-二甲基咪唑烷-2,4-二酮 羟基香豆素 美芬妥英 美芬妥英