cyclohexyl-phenyl-acetyl chloride | 49802-71-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cyclohexyl-phenyl-acetyl chloride
• 英文别名: phenylcyclohexylacetic acid chloride；cyclohexylphenylacetic acid chloride；2-Cyclohexyl-2-phenylacetyl chloride
• CAS: 49802-71-3
• 化学式: C₁₄H₁₇ClO
• 分子量: 236.741
• InChiKey: JXHHIAPAEUSUPW-UHFFFAOYSA-N

物化性质

• 沸点：
  108-110 °C(Press: 1 Torr)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  cyclohexyl-phenyl-acetyl chloride 在 盐酸 作用下， 以 乙醇 为溶剂， 生成 1-Phenyl-1-cyclohexyl-4-dimethylamino-butanon-(2)
  参考文献：
  名称：

  Physiologically Active Compounds. IV. Miscellaneous Compounds Related to Aminoethyl Esters of Benzilic Acid

  摘要：

  DOI：

  10.1021/jo01064a065
• 作为产物：
  描述：

  p-甲苯磺酸环己酯 在 正丁基锂 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 cyclohexyl-phenyl-acetyl chloride
  参考文献：
  名称：

  Discovery of new C3aR ligands. Part 2: Amino-piperidine derivatives

  摘要：

  The synthesis and structure-activity relationships against the C3a receptor of a series of substituted aminopiperidine derivatives are reported. DMPK properties and functional activities of selected compounds are described. The compounds obtained are the first non-arginine ligands of C3aR. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.023

文献信息

• [EN] 2-SULFANYL-BENZOIMIDAZOL-1-YL-ACETIC ACID DERIVATIVES AS CRTH2 ANTAGONISTS<br/>[FR] DERIVES DE L'ACIDE 2-SULFANYL-BENZOIMIDAZOL-1-YL-ACETIQUE EN TANT QU'ANTAGONISTES DE CRTH2
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2006021418A1

  公开（公告）日：2006-03-02

  The invention relates to 2-sulfanyl-benzoimidazol-1-yl-acetic acid derivatives and their use as potent 'chemoattractant receptor-homologous molecule expressed on Th2 cells' antagonists in the treatment of prostaglandin mediated diseases, to pharmaceutical compositions containing these derivatives and to processes for their preparation.

  这项发明涉及2-硫代基苯并咪唑-1-基乙酸衍生物及其在治疗前列腺素介导的疾病中作为强效“趋化受体同源分子在Th2细胞上表达”的拮抗剂的用途，涉及含有这些衍生物的药物组合物以及其制备方法。
• Synthesis, NMR spectroscopy study, and antimuscarinic activity of a series of 2-(Acyloxymethyl)-1,3-dioxolanes
  作者：Luca Malmusi、Adele Mucci、Luisa Schenetti、Ugo Gulini、Gabriella Marucci、Livio Brasili

  DOI：10.1016/s0968-0896(96)00223-4

  日期：1996.12

  and tested as potential muscarinic antagonists. The compounds display moderate to low affinity for the three receptor subtypes M1-M3, with some of them showing a significant selectivity for the M3 subtype. The configurational and conformational properties were studied using NOE experiments and vicinal coupling constants. The 1H and 13C NMR chemical shifts show stereochemically dependent trends. Quantitative

  合成了一系列带有羟甲基或酯官能团的基于1,3-二氧戊环的配体，并将其作为潜在的毒蕈碱拮抗剂进行了测试。这些化合物对三种受体亚型M1-M3表现出中等至低的亲和力，其中一些对M3亚型表现出显着的选择性。使用NOE实验和邻近耦合常数研究了构型和构象性质。1H和13C NMR化学位移显示立体化学依赖性趋势。构象种群的定量分析表明，环外CH 2 N CH 3）3基团在顺式异构体中普遍以伪轴向取向，在反式异构体中以伪赤道取向为主。
• Synthesis, Antimuscarinic Activity and Quantitative Structure-Activity Relationship (QSAR) of Tropinyl and Piperidinyl Esters.
  作者：Rong XU、Meng-Kwoon SIM、Mei-Lin GO

  DOI：10.1248/cpb.46.231

  日期：——

  A series of tropinyl and piperidinyl esters was synthesized and evaluated for inhibitory activities on the endothelial muscarinic receptors of rat (M3) and rabbit (M2) aorta. Some of the esters (cyclohexylphenylglycolates and cyclohexylphenylpropionates) were found to be better antimuscarinic compounds than standard M2 and M3 inhibitors such as AFDX116 and 4-diphenylacetoxy-N-methylpiperidine (DAMP), with pKEC50 values in the range of 8-9. A few esters were found to be more selective M3 than M2 inhibitors, but these tended to have low activities. The hydrophobic, electronic and steric characteristics of these esters were correlated with antimuscarinic activity by using appropriate parameters representing hydrophobicity (HPLC capacity factor, log kw), size (molecular volume) and electronic character (Taft's polar substituent constant σ* and 13C chemical shift difference Δδ). Finally, 92% of the M2-inhibitory activities of the esters could be accounted for by the size and electronic character σ* of the side chain. In contrast, the M3-inhibitory activities of these esters were mainly attributed to the electronic nature (σ*, Δδ) of the side chain, with good activity being associated with electron-withdrawing groups. Visualization of the comparative molecular field analysis (CoMFA) steric and electrostatic fields provided further confirmation of the structure-activity relationship (SAR) derived from traditional quantitative structure-activity relationship (QSAR) approaches.

  一系列トロピニル（tropinyl）およびピペリジニル（piperidinyl）エステルが合成され、ラット（M3）およびウサギ（M2）大動脈の内皮ムスカリン受容体に対する阻害活性が評価された。いくつかのエステル（シクロヘキシルフェニルグリコレートおよびシクロヘキシルフェニルプロピオネート）は、標準的なM2およびM3阻害剤であるAFDX116および4-ジフェニルアセトキシ-N-メチルピペリジン（DAMP）よりも優れた抗ムスカリン化合物であり、pKEC50値は8-9の範囲であった。いくつかのエステルはM2よりもM3阻害剤としてより選択的であることが判明したが、これらは活性が低い傾向にあった。これらのエステルの親水性、電子的および立体特性は、親水性（HPLC容量係数、log kw）、サイズ（分子体積）および電子的特性（Taftの極性置換基定数σ*および13C化学シフト差Δδ）を表す適切なパラメータを用いて抗ムスカリン活性と相関づけられた。最後に、エステルのM2阻害活性の92%は側鎖のサイズおよび電子的特性σ*によって説明できた。対照的に、これらのエステルのM3阻害活性は主に側鎖の電子的性質（σ*、Δδ）によるものであり、優れた活性は電子引き抜き基に関連していた。比較分子場分析（CoMFA）の立体および静電場の可視化は、従来の定量的構造活性相関（QSAR）アプローチから導出された構造活性相関（SAR）のさらなる確認を提供した。
• Soft drugs. 3. A new class of anticholinergic agents
  作者：Nicholas Bodor、Ross Woods、Colin Raper、Pauline Kearney、James J. Kaminski

  DOI：10.1021/jm00179a002

  日期：1980.5

  hindered "umbrella" acids and cholinergics when derivatives of simple aliphatic acids. The more potent anticholinergics have up to 10 times higher acetylcholine antagonist activity than atropine, but they have a much shorter duration of action. The compounds cleave hydrolytically with simultaneous destruction of the quaternary head. The compounds are promising as selective, local agents, particularly as

  设计并合成了一类新的抗毒蕈碱药物。这些化合物是“软”季铵酯，其中只有一个碳原子将酯氧和季头分开。当衍生自受阻的“伞”酸时，该化合物是有效的抗胆碱能药，而当衍生自简单脂肪酸时，这些化合物是胆碱能药。与阿托品相比，更有效的抗胆碱能药具有高达10倍的乙酰胆碱拮抗剂活性，但作用时间却短得多。该化合物水解裂解，同时破坏四级头。该化合物有望作为选择性的局部药物，特别是作为内分泌出汗的抑制剂。
• Synthesis and pharmacological properties of soft drug derivatives related to perhexiline
  作者：Gilbert Marciniak、Dominique Decolin、Gerard Leclerc、Nicole Decker、Jean Schwartz

  DOI：10.1021/jm00120a007

  日期：1988.12

  cyclohexylaralkylamines II based on the "soft drug" concept and incorporating an amide function were synthesized. In a preliminary screening, compounds were evaluated for their alpha-adrenolytic activities. Several derivatives, especially N-(cyclohexylphenylmethyl)-2-(cyclohexyl-methylamino)acetamide (3), N-(cyclohexylphenylmethyl)-2-(homoveratrylmethylamino)acetam ide (7), and N-[2-(cyclohexylamino)ethyl]-alpha-

  为了减少哌克昔林的毒性，合成了一系列基于“软药物”概念并结合酰胺功能的27种环己基烷基胺II。在初步筛选中，对化合物的α-肾上腺素分解活性进行了评估。几种衍生物，尤其是N-（环己基苯基甲基）-2-（环己基甲基氨基）乙酰胺（3），N-（环己基苯基甲基）-2-（全过甲基甲基氨基）乙酰胺（7）和N- [2-（环己基氨基）乙基] -α-环己基苯乙酰胺（23）在大鼠主动脉条中的体外活性范围与哌己昔林相同。然后研究了这三种分子的体外代谢，并将其与哌己昔林进行了比较。研究了在II上引入各种N-芳烷基胺基对α-肾上腺素解活性的影响。