4-(2,6-二氯苯基)哌啶 | 82211-90-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 4-(2,6-二氯苯基)哌啶
• 英文名称: 4-(2,6-dichlorophenyl)piperidine
• 英文别名: 4-(2,6-dichloro-phenyl)-piperidine
• CAS: 82211-90-3
• 化学式: C₁₁H₁₃Cl₂N
• mdl: MFCD11899285
• 分子量: 230.137
• InChiKey: SZSOOIJVCGFMHM-UHFFFAOYSA-N

物化性质

• 熔点：
  210-215℃
• 沸点：
  291℃
• 密度：
  1.207
• 闪点：
  130℃

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(2,6-二氯苯基)哌啶 在 盐酸 、 sodium hydroxide 、 硼烷四氢呋喃络合物 、 四丁基溴化铵 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 61.0h， 生成 1-benzyl-2-[4-(2,6-dichloro-phenyl)-piperidin-1-ylmethyl]-1H-indole hydrochloride
  参考文献：
  名称：

  [EN] SUBSTITUTED INDOLE LIGANDS FOR THE ORL-1 RECEPTOR
  [FR] LIGANDS D'INDOLE SUBSTITUES DESTINES UN RECEPTEUR ORL-1

  摘要：

  描述了用于调节ORL-1受体活性的新配体，适用于需要此类受体的患者，并用于预防和治疗依赖于该受体刺激的疾病。这些新化合物符合结构式（I），其中Q是式（II）的一个部分，而R、R0、R1、R2、R3、R4、R5、R6在描述中进一步定义。

  公开号：

  WO2005005411A1
• 作为产物：
  描述：

  4-(2,6-二氯苯基)哌啶-2,6-二酮 在 dimethyl sulfide borane 、 盐酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以35%的产率得到4-(2,6-二氯苯基)哌啶
  参考文献：
  名称：

  Structure–activity studies on the nociceptin/orphanin FQ receptor antagonist 1-benzyl-N-{3-[spiroisobenzofuran-1(3H),4′-piperidin-1-yl]propyl} pyrrolidine-2-carboxamide

  摘要：

  Twelve derivatives of the nociceptin/orphanin FQ (N/OFQ) receptor (NOP) antagonist 1-benzyl-N-{3-[spiroisobenzofuran-1(3H),4'-piperidin-1-yl]propyl} pyrrolidine-2-carboxamide (Comp 24) were synthesised and tested in binding experiments performed on CHOhNOP cell membranes. Among them, a novel interesting NOP receptor antagonist (compound 35) was identified by blending chemical moieties taken from different NOP receptor ligands. In vitro in various assays, Compound 35 consistently behaved as a pure, highly potent (pA(2) in the range 8.0-9.9), competitive and NOP selective antagonist. However compound 35 was found inactive when challenged against N/OFQ in vivo in the mouse tail withdrawal assay. Thus the usefulness of the novel NOP ligand compound 35 is limited to in vitro investigations. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.068

文献信息

• Modified Synthesis of NOP Receptor Antagonist SB612111
  作者：Yanan Zhang、David Perrey、Jun-Xu Li

  DOI：10.1055/s-0036-1588379

  日期：——

  (±)-6-methyl-12-oxatricyclo[8.2.1.02,7]trideca-2,4,6-trien-11-ol and 4-(2,6-dichlorophenyl)piperidine in the diastereoselective synthesis. We have thus explored various reaction conditions and successfully improved the yields for the necessary synthetic steps. We herein report our modified synthesis of SB612111 as the cis-diastereomers. SB612111 [(5S,7S)-7-[4-(2,6-dichlorophenyl)piperidin-1-yl]methyl}-1-methyl-6

  摘要 SB612111 [（5 S，7 S）-7-[4-（2,6-二氯苯基）哌啶-1-基]甲基} -1-甲基-6,7,8,9-四氢-5 H-苯并[7] annulen-5-ol]是一种有效的，选择性的伤害感受/孤儿蛋白FQ肽（NOP）受体的拮抗剂。在合成顺式-SB612111以支持正在进行的动物研究的过程中，专利文献中公开的合成的几个关键步骤以低收率进行，尤其是通往关键中间体4-（2,6-二氯苯基）的途径哌啶，还原7- [4-（2,6-二氯苯基）哌啶-1-羰基] -1-甲基-6,7,8,9-四氢-5 H-苯并[7]环戊烯-5- ，形成（±）-6-甲基-12-氧三环[8.2.1.0 2,7] trideca-2,4,6-trien-11-one和（±）-6-甲基-12-氧三环[8.2.1.0 2,7 ] trideca-2,4,6-trien-之间的最终还原胺化非对映选择性合成中的11-ol和4-（2
• Substituted indole ligands for the ORL-1 receptor
  申请人：NIKEM RESEARCH S.R.L.

  公开号：EP1676843A1

  公开（公告）日：2006-07-05

  New ligands for the ORL-1 receptor are described, useful for modulating the activity of said receptors in a patient in need thereof, and for preventing and treating illnesses dependent on the stimulation of this receptor. The new compounds conform to structural formula (I) wherein R1, R2, R3, R4 are further defined in the description.

  本文介绍了ORL-1受体的新配体，可用于调节需要该受体活性的患者的活性，并预防和治疗依赖于该受体刺激的疾病。新化合物符合结构式（I），其中R1、R2、R3、R4在描述中进一步定义。
• Preparation of benzosuberonylpiperidine compounds
  申请人：Palombi Giovanni

  公开号：US20050059700A1

  公开（公告）日：2005-03-17

  Diastereoselective and enantioselective synthetic routes for the preparation of compounds of formula (I): or derivatives thereof, wherein: R is C 1-6 alkyl, C 3-7 cycloalkyl, C 1-6 alkoxy, hydroxy, halo, C 1-6 alkenyl, C 1-6 alkynyl, amino, C 1-6 alkylamino, di(C 1-6 alkyl)amino, hydroxyC 1-6 alkyl, C 1-6 alkoxyC 1-6 alkyl, arylC 1-6 alkoxy, heteroarylC 1-6 alkoxy, aminoC 1-6 alkyl, (C 1-6 alkyl)aminoC 1-6 alkyl, di(C 1-6 alkyl)aminoC 1-6 alkyl, arylC 1-6 alkylamino, heteroarylC 1-6 alkylamino; R 1 is hydrogen or R; R 2 is hydroxy, C 1-6 alkoxy, amino, C 1-6 alkylamino, di(C 1-6 alkyl)amino; R 3 and R 4 are each independently selected from the list consisting of perhaloC 1-6 alkyl, hydrogen, halo, C 1-6 alkyl, C 1-6 alkoxy, hydroxy, amino, C 1-6 alkylamino, di(C 1-6 alkyl)amino, hydroxyC 1-6 alkyl, C 1-6 alkoxyC 1-6 alkyl, aminoC 1-6 alkyl, (C 1-6 alkyl)aminoC 1-6 alkyl, di(C 1-6 alkyl)aminoC 1-6 alkyl, aryl, and COX wherein X may be hydroxy, C 1-6 alkoxy, C 1-6 alkyl, amino, C 1-6 alkylamino, or di(C 1-6 alkyl)amino; and wherein any alkyl group or the alkyl moiety of any group containing such a moiety may be substituted one or more times by halo.

  具有公式（I）的化合物或其衍生物的对映选择性和对映选择性合成途径，其中：R是C1-6烷基，C3-7环烷基，C1-6烷氧基，羟基，卤素，C1-6烯基，C1-6炔基，氨基，C1-6烷基氨基，二（C1-6烷基）氨基，羟基C1-6烷基，C1-6烷氧基C1-6烷基，芳基C1-6烷氧基，杂环芳基C1-6烷氧基，C1-6烷基氨基，（C1-6烷基）氨基C1-6烷基，二（C1-6烷基）氨基C1-6烷基，芳基C1-6烷基氨基，杂环芳基C1-6烷基氨基; R1是氢或R; R2是羟基，C1-6烷氧基，氨基，C1-6烷基氨基，二（C1-6烷基）氨基; R3和R4各自独立地从列表中选择，该列表包括全卤素C1-6烷基，氢，卤素，C1-6烷基，C1-6烷氧基，羟基，氨基，C1-6烷基氨基，二（C1-6烷基）氨基，羟基C1-6烷基，C1-6烷氧基C1-6烷基，C1-6烷基氨基，（C1-6烷基）氨基C1-6烷基，二（C1-6烷基）氨基C1-6烷基，芳基和COX，其中X可以是羟基，C1-6烷氧基，C1-6烷基，氨基，C1-6烷基氨基或二（C1-6烷基）氨基; 其中任何含有此类基团的烷基或烷基基团可以被卤素取代一次或多次。
• Substituted indole ligands for the orl-1 receptor
  申请人：Consonni Alessandra

  公开号：US20070197603A1

  公开（公告）日：2007-08-23

  New ligands for the ORL-1 receptor are described, useful for modulating the activity of said receptors in a patient in need thereof, and for preventing and treating illnesses dependent on the stimulation of this receptor. The new compounds conform to structural formula (I), wherein Q is a moiety of formula: and R, R 0 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 are further defined in the description.

  本文描述了ORL-1受体的新配体，可用于调节患者中该受体的活性，并用于预防和治疗依赖于该受体刺激的疾病。新化合物符合结构式（I），其中Q是以下式子的一个基团：而R，R0，R1，R2，R3，R4，R5，R6在描述中进一步定义。
• A Novel Class of Cycloalkano[<i>b</i>]pyridines as Potent and Orally Active Opioid Receptor-like 1 Antagonists with Minimal Binding Affinity to the hERG K⁺Channel
  作者：Takashi Yoshizumi、Hirobumi Takahashi、Hiroshi Miyazoe、Yuichi Sugimoto、Tomohiro Tsujita、Tetsuya Kato、Hirokatsu Ito、Hiroshi Kawamoto、Mioko Hirayama、Daisuke Ichikawa、Tomoko Azuma-Kanoh、Satoshi Ozaki、Yoshihiro Shibata、Takeshi Tani、Masato Chiba、Yasuyuki Ishii、Shoki Okuda、Kiyoshi Tadano、Takahiro Fukuroda、Osamu Okamoto、Hisashi Ohta

  DOI：10.1021/jm701590h

  日期：2008.7

  A series of compounds based on 7-[4-(2-methylphenyl)piperidin-1-yl]methyl}-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-9-ol ((-)-8b), a potent and selective opioid receptor-like 1 (ORL1) antagonist, was prepared and evaluated using structure-activity relationship studies with the aim of removing its affinity to human ether-a-go-go related gene (hERG) K+ channel. From these studies, 10l was identified as an optimized structure with respect to ORL1 antagonist activity, and affinity to the hERG K+ channel. Furthermore, 10l showed good in vivo antagonism with a wide therapeutic index in regards to adverse cardiovascular effects.