(4-carbamoyl-r-4-hydroxy-c-cyclohexyl)-carbamic acid tert butyl ester | 615568-57-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-carbamoyl-r-4-hydroxy-c-cyclohexyl)-carbamic acid tert butyl ester
• 英文别名: 1,1-Dimethylethyl N-[cis-4-(aminocarbonyl)-4-hydroxycyclohexyl]carbamate；tert-butyl N-(4-carbamoyl-4-hydroxycyclohexyl)carbamate
• CAS: 615568-57-5
• 化学式: C₁₂H₂₂N₂O₄
• 分子量: 258.318
• InChiKey: QGYXQBORNGRQOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-carbamoyl-r-4-hydroxy-c-cyclohexyl)-carbamic acid tert butyl ester 在 tris-(dibenzylideneacetone)dipalladium(0) 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 t-4-amino-1-hydroxy-r-cyclohexanecarboxylic acid (6-hydroxy-[1,5]naphthyridin-4-yl)-amide
  参考文献：
  名称：

  Novel cyclohexyl-amides as potent antibacterials targeting bacterial type IIA topoisomerases

  摘要：

  As part of our wider efforts to exploit novel mode of action antibacterials, we have discovered a series of cyclohexyl-amide compounds that has good Gram positive and Gram negative potency. The mechanism of action is via inhibition of bacterial topoisomerases II and IV. We have investigated various subunits in this series and report advanced studies on compound 7 which demonstrates good PK and in vivo efficacy properties. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.114
• 作为产物：
  描述：

  在 1% Pd/C 、 氢气 作用下， 以 甲醇 为溶剂， 60.0 ℃ 、827.39 kPa 条件下， 以95%的产率得到(4-carbamoyl-r-4-hydroxy-c-cyclohexyl)-carbamic acid tert butyl ester
  参考文献：
  名称：

  The design of efficient and selective routes to a key 1,4-cis-substituted cyclohexylamide intermediate

  摘要：

  This Letter describes the synthetic challenges in synthesising key 1,4-cis-substituted cyclohexylamide intermediate 1 for our research programme. Five different routes address the major issues of selectivity to afford the cis product in isomerically pure form and in high yield. Major purification issues were also encountered upon scaling some of the routes. The merits of the diverse routes are assessed and the reasoning given for which one was ultimately used for large-scale synthesis of 1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.03.083

文献信息

• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：GLAXO GROUP LTD

  公开号：WO2004002992A1

  公开（公告）日：2004-01-08

  Cyclohexane and cyclohexene derivatives and pharmaceutically acceptable derivatives thereof useful in methods of treatment of bacterial infections in mammals, particularly man. A compound of formula (I) or a pharmaceutically acceptable derivative thereof: (I) RA is an optionally substituted bicyclic carbocyclic or heterocyclic ring system of structure: containing 0-3 heteroatmoms in each ring in which: at least one of the rings (x) and (y) is aromatic; one of Z4 and Z5 is C or N and the other is C; Z3 is N, NR13, O, S(O)x, CO, CR1 or CR1R1a; Z1 and Z2 are indendently a 2 or 3 atom linker group each atom of which is independently selected from N, NR13, O, S(O)x, CO, CR1, and CR1R1a; such that each ring is independently substituted with 0-3 groups R1 and/or R1a. R4 is a group -CH2-R51in which R51 is selected from: (C4-8) alkyl; hydroxy (C4-8) alkyl; (C1-4)alkoxy (C4-8)alkyl; (C1-4) alkanoyloxy (C4-8) alkyl; (C3-8)cycloalkyl (C 4-8)alkyl;hydroxy-, (C1-6) alkoxy- or (C1-6) alkanoyloxy-(C3-8)cycloalkyl (C4-8)alkyl; cyano(C4-8)alkyl; (C4-8)alkenyl; (C4-8)alkynyl; tetrahydrofuryl; mono- or di-(C1-6)alkylamino (C4-8)alkyl; acylamino (C4-8)alkyl; C(1-6)alkyl- or acyl-aminocarbonyl (C4-8) alkyl; mono- or di- (C1-6)alkylamino(hydroxy) (C4-8)alkyl; or R4 is a group-U-R52 where R52 is an optionally substituted bicyclic carbocyclic or heterocyclic ring system (A): containing up to four heteroatoms in each ring in which at least one of rings (a) and (b) is aromatic; X1 is C or N when part of an aromatic ring or CR14 when part of a non-aromatic ring.

  环己烷和环己烯衍生物及其在治疗哺乳动物，特别是人类细菌感染方法中有用的药用可接受衍生物。一种公式(I)的化合物或其药用可接受的衍生物：(I) RA是一个可选地取代的双环碳环或杂环环系结构：包含每个环中的0-3个杂原子，其中：至少一个环(x)和(y)是芳香的；Z4和Z5中的一个为C或N，另一个为C；Z3是N，NR13，O，S(O)x，CO，CR1或CR1R1a；Z1和Z2是独立选择的2或3原子连接基团，每个原子独立地选自N，NR13，O，S(O)x，CO，CR1，和CR1R1a；使得每个环独立地用0-3个组R1和/或R1a取代。R4是一个组-CH2-R51，其中R51选自：(C4-8)烷基；羟基(C4-8)烷基；(C1-4)烷氧基(C4-8)烷基；(C1-4)烷酰氧基(C4-8)烷基；(C3-8)环烷基(C4-8)烷基；羟基-，(C1-6)烷氧基-或(C1-6)烷酰氧基-(C3-8)环烷基(C4-8)烷基；氰基(C4-8)烷基；(C4-8)烯基；(C4-8)炔基；四氢呋喃基；单或二-(C1-6)烷基氨基(C4-8)烷基；酰氨基(C4-8)烷基；C(1-6)烷基-或酰基-氨基甲酰基(C4-8)烷基；单或二-(C1-6)烷基氨基(羟基)(C4-8)烷基；或R4是一个组-U-R52，其中R52是一个可选地取代的双环碳环或杂环环系(A)：每个环中含最多四个杂原子，其中至少一个环(a)和(b)是芳香的；X1是C或N当其作为芳香环的一部分，或CR14当其作为非芳香环的一部分。
• [EN] NITROGEN-CONTAINING BICYCLIC HETEROCYCLES FOR USE AS ANTIBACTERIALS<br/>[FR] HETEROCYCLES BICYCLIQUES CONTENANT DE L'AZOTE ET UTILISES COMME PRODUITS ANTIBACTERIENS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO2003087098A1

  公开（公告）日：2003-10-23

  Cyclohexane and cyclohexene derivatives and pharmaceutically acceptable derivatives hereof useful in methods of treatment of bacterial infections in mammals, particularly man.

  环己烷和环己烯衍生物及其在哺乳动物，特别是人类细菌感染治疗方法中有用的药用可接受衍生物。
• Compounds
  申请人：Axten Michael Jeffrey

  公开号：US20060189604A1

  公开（公告）日：2006-08-24

  Cyclohexane and cyclohexene derivatives and pharmaceutically acceptable derivatives thereof useful in methods of treatment of bacterial infections in mammals, particularly man.

  环己烷和环己烯衍生物及其药学上可接受的衍生物在哺乳动物中，特别是人类中用于治疗细菌感染的方法中具有用途。
• Aminocyclohexene quinolines and their azaisosteric analogues with antibacterial activity
  申请人：Davies Thomas David

  公开号：US20060040925A1

  公开（公告）日：2006-02-23

  Cyclohexene derivatives and pharmaceutically acceptable derivatives thereof useful in methods of treatment of bacterial infections in mammals, particularly man.

  环己烯衍生物及其药学上可接受的衍生物，适用于哺乳动物，特别是人类的细菌感染治疗方法。
• Nitrogen-containing bicyclic heterocycles for use as antibacterials
  申请人：——

  公开号：US20040171620A1

  公开（公告）日：2004-09-02

  Cyclohexane and cyclohexene derivatives and pharmaceutically acceptable derivatives hereof useful in methods of treatment of bacterial infections in mammals, particularly man.

  Cyclohexane和cyclohexene衍生物及其药学上可接受的衍生物在哺乳动物，特别是人类的治疗细菌感染的方法中是有用的。