8-chlorooctanoyl chloride | 99219-17-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: 8-chlorooctanoyl chloride
• 英文别名: 8-chlorooctanoic acid chloride
• CAS: 99219-17-7
• 化学式: C₈H₁₄Cl₂O
• 分子量: 197.105
• InChiKey: CUASUSAFYJAUDE-UHFFFAOYSA-N

物化性质

• 沸点：
  137-140 °C(Press: 15 Torr)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8-chlorooctanoyl chloride 在 三乙胺 、 N,N-二异丙基乙胺 、 potassium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 8-(4-(3,5-bis(benzyloxy)benzyl)piperazin-1-yl)-1-(1-methyl-4,10-dihydrobenzo[b]pyrazolo[3,4-e][1,4]diazepin-5(1H)-yl)octan-1-one
  参考文献：
  名称：

  Flexible analogues of WAY-267,464: Synthesis and pharmacology at the human oxytocin and vasopressin 1 a receptors

  摘要：

  A previously identified, non-peptidic oxytocin (OT) receptor agonist WAY-267,464 (1) and nine novel derivatives (3, 4a-7a, 4b-7b) were synthesised and evaluated in vitro with the aim of systematically exploring hydrogen bonding interactions and ligand flexibility. All analogues were subjected to competition radioligand binding assays at human oxytocin (OT) and arginine vasopressin 1a (V-1a) receptors. Physiological activity was determined using whole cell IP1 accumulation assays. Under these conditions, WAY -267,464 had higher affinity for the V-1a receptor compared to the OT receptor (8.5x more selective) with poor functional selectivity (2x selective for OT receptor agonism over V-1a receptor antagonism). Methylation of the resorcinol moiety (3) reversed the OT receptor pharmacological profile, removing agonist activity and inducing antagonist activity, without altering V-1a receptor pharmacology. All flexible tethered derivatives removed OT receptor affinity and activity resulting in the generation of highly selective V-1a receptor ligands. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.11.050
• 作为产物：
  描述：

  8-羟基辛酸 在 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 13.5h， 以10.9 g的产率得到8-chlorooctanoyl chloride
  参考文献：
  名称：

  Polymethylene derivatives of nucleic bases with ω-functional groups: VI. [8-(2-oxocyclohexyl)-9-oxooctyl]pyrimidines as potential inhibitors of pyrimidine phosphorylases

  摘要：

  新型多甲烯基衍生物的核苷碱基在ω位点引入了β-二酮功能，通过对尿嘧啶、胸苷和胞嘧啶进行烷基化制备。研究了它们的物理化学性质及对大肠杆菌尿苷酶和胸苷酶的影响。

  DOI：

  10.1134/s1068162008010093

文献信息

• Polymethylene derivatives of nucleic bases with ω-functional groups: VII. Cytotoxicity in the series of N-(2-oxocyclohexyl)-ω-oxoalkyl-substituted purines and pyrimidines
  作者：V. V. Komissarov、G. M. Volgareva、Ya. S. Ol’shanskaya、M. E. Chernyshova、L. E. Zavalishina、G. A. Frank、A. A. Shtil’、A. M. Kritzyn

  DOI：10.1134/s1068162009010105

  日期：2009.1

  New polymethylene derivatives of nucleic bases with a beta-diketo function in the omega-position were obtained by alkylation of uracil, thymine, cytosine, hypoxanthine, adenine, and N(2)-isobutyryl guanine with 2-omega-chloroal-kanoyl)cyclohexanones. The physical and chemical characteristics of the compounds synthesized and their effect on the K562 and HCT116 tumor cell lines were studied.

  通过在尿嘧啶，胸腺嘧啶，胞嘧啶，次黄嘌呤，腺嘌呤和N（2）-异丁酰基鸟嘌呤与2-ω-氯代-醛基-卡诺基）环己酮的烷基化反应中获得在ω-位具有β-二酮功能的核酸碱基的新的多亚甲基衍生物。研究了合成化合物的理化特性及其对K562和HCT116肿瘤细胞系的影响。
• US7232642B2
  申请人：——

  公开号：US7232642B2

  公开（公告）日：2007-06-19
• US7556908B2
  申请人：——

  公开号：US7556908B2

  公开（公告）日：2009-07-07
• Flexible analogues of WAY-267,464: Synthesis and pharmacology at the human oxytocin and vasopressin 1 a receptors
  作者：William T. Jorgensen、Damien W. Gulliver、Eryn L. Werry、Tristan Reekie、Mark Connor、Michael Kassiou

  DOI：10.1016/j.ejmech.2015.11.050

  日期：2016.1

  A previously identified, non-peptidic oxytocin (OT) receptor agonist WAY-267,464 (1) and nine novel derivatives (3, 4a-7a, 4b-7b) were synthesised and evaluated in vitro with the aim of systematically exploring hydrogen bonding interactions and ligand flexibility. All analogues were subjected to competition radioligand binding assays at human oxytocin (OT) and arginine vasopressin 1a (V-1a) receptors. Physiological activity was determined using whole cell IP1 accumulation assays. Under these conditions, WAY -267,464 had higher affinity for the V-1a receptor compared to the OT receptor (8.5x more selective) with poor functional selectivity (2x selective for OT receptor agonism over V-1a receptor antagonism). Methylation of the resorcinol moiety (3) reversed the OT receptor pharmacological profile, removing agonist activity and inducing antagonist activity, without altering V-1a receptor pharmacology. All flexible tethered derivatives removed OT receptor affinity and activity resulting in the generation of highly selective V-1a receptor ligands. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Polymethylene derivatives of nucleic bases with ω-functional groups: VI. [8-(2-oxocyclohexyl)-9-oxooctyl]pyrimidines as potential inhibitors of pyrimidine phosphorylases
  作者：V. V. Komissarov、N. G. Panova、A. M. Kritzyn

  DOI：10.1134/s1068162008010093

  日期：2008.1

  New polymethylene derivatives of nucleic bases with β-diketo function in ω-position were prepared by alkylation of uracil, thymine, and cytosine. Their physicochemical properties and effect on the E. coli uridine and thimidine phosphorylases were studied.

  新型多甲烯基衍生物的核苷碱基在ω位点引入了β-二酮功能，通过对尿嘧啶、胸苷和胞嘧啶进行烷基化制备。研究了它们的物理化学性质及对大肠杆菌尿苷酶和胸苷酶的影响。