1-环丙基哌嗪-4-羧酸叔丁酯 | 77278-34-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 1-环丙基哌嗪-4-羧酸叔丁酯
• 英文名称: 4-cyclopropylpiperazine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl piperazine-1-carboxylate；tert-butyl 4-cyclopropylpiperazine-1-carboxylate；tert-butyl 1-cyclopropylpiperazine-4-carboxylate；N-tert-butoxycarbonyl-N-cyclopropylpiperazine；1-cyclopropylpiperazine-4-carboxylic acid tert-butyl ester；1-cyclopropyl-4-(1,1-dimethylethoxycarbonyl)piperazine；N-Boc-N-cyclopropylpiperazine
• CAS: 77278-34-3
• 化学式: C₁₂H₂₂N₂O₂
• 分子量: 226.319
• InChiKey: UNCLAXHNVIYBNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  1-环丙基哌嗪-4-羧酸叔丁酯 在 盐酸 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 30.25h， 生成 (4-环丙基哌嗪-1-基)-[4-(吗啉-4-基甲基)苯基]甲酮
  参考文献：
  名称：

  Novel Benzamide-Based Histamine H3 Receptor Antagonists: The Identification of Two Candidates for Clinical Development

  摘要：

  The preclinical characterization of novel phenyl(piperazin-1-yl)methanones that are histamine H-3 receptor antagonists is described. The compounds described are high affinity histamine H-3 antagonists. Optimization of the physical properties of these histamine H-3 antagonists led to the discovery of several promising lead compounds, and extensive preclinical profiling aided in the identification of compounds with optimal duration of action for wake promoting activity. This led to the discovery of two development candidates for Phase I and Phase II clinical trials.

  DOI：

  10.1021/ml5005156
• 作为产物：
  描述：

  N-Boc-哌嗪 在 tetraisopropyl titanate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 1-环丙基哌嗪-4-羧酸叔丁酯
  参考文献：
  名称：

  一种合成1-环丙基哌嗪的方法

  摘要：

  本发明公开了一种合成1‑环丙基哌嗪的方法，包括：以式1所示的1‑叔丁氧羰基哌嗪为起始原料，与过量的取代甲酸烷基酯HCOOR1发生甲酰化反应生成式2所示的4‑甲酰基哌嗪‑1‑羧酸叔丁酯，然后在钛酸四烷基酯的催化下与乙基溴化镁在溶剂中发生N‑环丙基化的反应生成中间体3，中间体3在酸的作用下于溶剂中发生脱保护基的反应生成式4所示的目标产物1‑环丙基哌嗪，反应路线如下：#imgabs0#其中，所述取代甲酸烷基酯HCOOR1结构中的取代基R1为C1‑C4烷基。本发明起始原料廉价易得，合成路线短，各步反应条件温和，总体收率高，具有很好的工业化前景。

  公开号：

  CN117886777A

文献信息

• Substituted piperazines and diazepanes
  申请人：——

  公开号：US20040019039A1

  公开（公告）日：2004-01-29

  A novel class of substituted piperazines and diazepanes, pharmaceutical compositions comprising them and use thereof in the treatment of diseases and disorders related to the histamine H3 receptor. More particularly, the compounds are useful for the treatment of diseases and disorders in which an interaction with the histamine H3 receptor is beneficial.

  一种新型的取代哌嗪和二氮杂环庚烷类化合物，包括它们的药物组合物以及在治疗与组胺H3受体相关的疾病和紊乱中的应用。更具体地说，这些化合物对于治疗需要与组胺H3受体相互作用有益的疾病和紊乱是有用的。
• Copper-promoted N-cyclopropylation of anilines and amines by cyclopropylboronic acid
  作者：Sébastien Bénard、Luc Neuville、Jieping Zhu

  DOI：10.1039/b925499d

  日期：——

  Reaction of anilines, primary and secondary aliphatic amines with cyclopropylboronic acid in dichloroethane in the presence of Cu(OAc)(2) (1 equiv.), 2,2'-bipyridine (1 equiv.) and sodium carbonate or sodium bicarbonate (2 equiv.) under air atmosphere afforded the corresponding N-cyclopropyl derivatives in good to excellent yields.

  在Cu（OAc）（2）（1当量），2,2'-联吡啶（1当量）和碳酸钠或碳酸氢钠（2）存在下，苯胺，脂肪族伯胺和仲胺与环丙基硼酸在二氯乙烷中的反应当量）在空气气氛下以良好至优异的产率得到相应的N-环丙基衍生物。
• [EN] AMINOPYRIMIDINE HETEROCYCLIC COMPOUND WITH ADENOSINE RECEPTOR ANTAGONISTIC ACTIVITY<br/>[FR] COMPOSÉ AMINOPYRIMIDINE HÉTÉROCYCLIQUE PRÉSENTANT UNE ACTIVITÉ ANTAGONISTE DU RÉCEPTEUR DE L'ADÉNOSINE
  申请人：SUZHOU YUNXUAN YIYAO KEJI YOUXIAN GONGSI

  公开号：WO2017088755A1

  公开（公告）日：2017-06-01

  Disclosed hereinis an aminopyrimidine heterocyclic compound with adenosine receptor antagonistic activity, comprising a compound of the general formula (I), or a pharmaceutically acceptable salt thereof. The aminopyrimidine heterocyclic compound with adenosine receptor antagonistic activitydisclosed herein can be used as an effective adenosine receptor antagonist, and can be used for the treatment or prevention of disorders caused by abnormal level of adenosine.

  本文披露了一种具有腺苷受体拮抗活性的氨基嘧啶杂环化合物，包括一般式(I)的化合物或其药学上可接受的盐。本文披露的具有腺苷受体拮抗活性的氨基嘧啶杂环化合物可用作有效的腺苷受体拮抗剂，并可用于治疗或预防由腺苷水平异常引起的疾病。
• PYRAZOLE DERIVATIVES
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP1762568A1

  公开（公告）日：2007-03-14

  A compound represented by formula (I): (wherein Ar1 represents a phenyl group which may have 1 to 3 substituents, or a non-substituted 5- or 6-membered aromatic heterocyclic group; Ar2 represents (i) a non-substituted phenyl group, (ii) a phenyl group which has been substituted by a lower alkyl group having 1 to 3 groups or atoms selected from among a carbamoyl group, an amino group, a hydroxyl group, a lower alkoxy group, and a halogen atom, or (iii) a 5- or 6-membered nitrogen-containing aromatic heterocyclic group which has been substituted by 1 to 3 groups or atoms selected from among a lower alkyl group, a lower alkynyl group, a lower alkanoyl group, a carbamoyl group, a cyano group, an amino group, a hydroxyl group, a lower alkoxy group, and a halogen atom; and X represents a group represented by formula (II): (wherein the ring structure represents a 4- to 7-membered heterocyclic group which may have, in addition to the nitrogen atom shown in formula (II), one heteroatom selected from among nitrogen, oxygen, and sulfur, and which may be substituted by 1 to 4 groups or atoms selected from among a lower alkyl group, a carbamoyl group, an amino group, a hydroxyl group, a lower alkoxy group, an oxo group, a lower alkanoyl group, a lower alkylsulfonyl group, and a halogen atom)), a salt thereof, a solvate of the compound or the salt, and a drug.

  由式(I)表示的化合物： （其中Ar1代表可能具有1到3个取代基的苯基，或者是非取代的5-或6-成员芳香杂环基团；Ar2代表（i）非取代的苯基团，（ii）已被1到3个来自羰胺基、氨基、羟基、低烷氧基和卤原子的群或原子取代的较低烷基基团取代的苯基团，或者（iii）已被1到3个来自低烷基基团、低炔基基团、低烷酰基团、羰胺基、氰基、氨基、羟基、低烷氧基和卤原子的群或原子取代的5-或6-成员含氮芳香杂环基团；X代表由式(II)表示的基团： （其中环结构表示可能具有除了式(II)中显示的氮原子之外，从氮、氧和硫中选择的一个杂原子的4-到7-成员杂环基团，并且可能被1到4个来自低烷基基团、羰胺基、氨基、羟基、低烷氧基、氧基、低烷酰基团、低烷基磺酰基团和卤原子的群或原子取代）），其盐，该化合物或其盐的溶剂化合物，以及药物。
• A simple method for the formation of cyclopropylamines: the first synthesis of tricyclopropylamine
  作者：Melissa L. Gillaspy、Bruce A. Lefker、William A Hada、Dennis J. Hoover

  DOI：10.1016/0040-4039(95)01560-4

  日期：1995.10

  mild, one-step method to cyclopropylate amines is described. Treatment of a variety of secondary and primary amines with [(1-ethoxycyclopropyl)oxy]trimethylsilane and sodium cyanoborohydride in methanol gave mono- and dicyclopropylamines in good yield. Sterically hindered di- and tricyclopropylamines, including the previously unreported tricyclopropylamine, were prepared using this method. The pKas of

  描述了一种温和的一步法制备环丙基胺。用[（1-乙氧基环丙基）氧基]三甲基硅烷和氰基硼氢化钠在甲醇中处理各种仲胺和伯胺，可得到高产率的单环丙胺和二环丙胺。使用该方法制备了位阻二和三环丙胺，包括以前未报道的三环丙胺。测量了一些单，二和三环丙胺的pKa，显示每个添加的环丙基减少了约1-2 pKa单位。