3-fluorobenzhydryl chloride | 13391-48-5

• 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: 3-fluorobenzhydryl chloride
• 英文别名: (3-FC6H4)PhCH-Cl；3-Fluor-benzhydrylchlorid；1-[Chloro(phenyl)methyl]-3-fluorobenzene
• CAS: 13391-48-5
• 化学式: C₁₃H₁₀ClF
• 分子量: 220.674
• InChiKey: VYWDURRWGGJCGB-UHFFFAOYSA-N

物化性质

• 沸点：
  292.3±25.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-fluorobenzhydryl chloride 在 水 作用下， 以 乙腈 为溶剂， 生成 (3-氟苯基)-苯基甲醇
  参考文献：
  名称：

  氟代二苯甲基衍生物的溶剂分解动力学：用于开发综合核偏度量表的参考电离

  摘要：

  制备了一系列间氟取代的二苯甲基氯化物、溴化物、甲磺酸盐和甲苯磺酸盐 1-X 至 5-X，并在各种溶剂中进行溶剂分解反应。发现观察到的一阶速率常数 ks (25 °C) 遵循相关方程 log ks (25 °C) = sf (N f + E f )，这使我们能够确定这些不稳定的电离参数 E f二苯甲基阳离子和一系列离去基团/溶剂组合的离核参数 N f , sf 。

  DOI：

  10.1002/ejoc.200901400
• 作为产物：
  描述：

  (3-氟苯基)-苯基甲醇 在 氯化亚砜 作用下， 生成 3-fluorobenzhydryl chloride
  参考文献：
  名称：

  3'-Chloro-3α-（二苯基甲氧基）托烷，而不是4'-chloro-3α-（二苯基甲氧基）托烷产生可卡因样的行为特征。

  摘要：

  通常，邻位取代的类似物在结合和抑制多巴胺转运蛋白上的作用均不如苄索平或其他被芳基取代的同系物强。还测试了类似物在去甲肾上腺素和血清素转运蛋白以及毒蕈碱m1受体上的结合。本研究中没有化合物与去甲肾上腺素或5-羟色胺转运蛋白具有高亲和力，但均与毒蕈碱型m1受体具有高亲和力（K1 = 0.41-2.52 nM）。有趣的是，3'-chloro-3α-（二苯基甲氧基）托烷（5c）在受过训练可从盐水中区分10 mg / kg可卡因的动物中产生类似可卡因的作用，不像其4'-Cl同系物和所有先前评估过的苄索平类似物。

  DOI：

  10.1021/jm950782k

文献信息

• Effects of Ionic Liquids on the Nucleofugality of Chloride
  作者：Maxwell D. Coney、Daniel C. Morris、Alyssa Gilbert、Stuart W. Prescott、Ronald S. Haines、Jason B. Harper

  DOI：10.1021/acs.joc.1c02043

  日期：2022.2.4

  The nucleofugality of chloride has been measured in solvent mixtures containing ionic liquids for the first time, allowing reactivity in these solvents to be put in context with molecular solvents. Using well-described electrofuges, solvolysis rate constants were determined in mixtures containing different proportions of ethanol and the ionic liquid 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide;

  首次在含有离子液体的溶剂混合物中测量了氯化物的核逸散性，从而将这些溶剂中的反应性与分子溶剂结合起来。使用描述良好的电驱动器，在含有不同比例乙醇和离子液体 1-丁基-3-甲基咪唑双（三氟甲磺酰）亚胺的混合物中测定溶剂分解速率常数；可以使用离子液体与沿反应坐标的物质的相互作用来解释随着混合物变化观察到的不同溶剂效应，使用温度依赖性动力学研究确定。溶剂解数据可以确定这些混合物中氯化物的离核性，该离核性随反应混合物中盐的比例而变化，定量证明反应混合物中离子液体的量在确定反应结果中的重要性。在另外七种离子液体中测定了氯化物的离核性数据，显示反应性变化超过一个数量级。该结果说明离子液体的组分在确定反应结果中是关键的。总体而言，这项工作定量地扩展了对离子液体中溶剂效应的理解，并证明了此类信息可用于合理选择离子液体以控制反应结果的潜力。该结果说明离子液体的组分在确定反应结果中是关键的。总体而言，这项工作定
• Diphenylcarbinyl Derivatives. I. Solvolysis of some Monosubstituted Benzhydryl Chlorides
  作者：Shinya Nishida

  DOI：10.1021/jo01284a600

  日期：1967.9
• Ring-substituted histaprodifen analogues as partial agonists for histamine H1 receptors: synthesis and structure–activity relationships
  作者：S Elz

  DOI：10.1016/s0223-5234(00)00105-7

  日期：2000.1

  Thirteen racemic benzene ring-substituted analogues of histaprodifen (8a; 2-[2-(3,3-diphenylpropyl)-1H-imidazol-4-yl]ethanamine), a novel lead for potent and selective histamine H-1-receptor agonists, have been prepared from substituted 4,4-diphenylbutyronitriles 5 via cyclization of the corresponding methyl butyrimidates 6 with 2-oxo-4-phthalimido-1-butyl acetate in liquid ammonia, followed by deprotection. Nitriles 5 were accessible by alkylation of either substituted diphenylmethanes with 3-bromopropionitrile or diethyl malonate with substituted 1-chloro-diphenylmethanes and subsequent standard reactions. The title compounds 8 displayed partial agonism on contractile H-1 receptors of the guinea-pig ileum (E-max = 2-98% relative to histamine) and, compared with the endogenous agonist, were endowed with agonist potencies of 4-92%. The meta fluorinated (gc) and meta chlorinated (8f) analogues showed the highest relative potency in this series (95% confidence Limits 85-99% and 78-102%), but did not exceed the value of the lead 8a (99-124%). Compound 8c (2-[2-[3-(3-fluorophenyl)-3-phenylpropyl]-1H-imidazol-4-yl]ethanamine) was a partial agonist at contractile H-1 receptors of the guinea-pig aorta (relative potency 154% vs. 100% for histamine) and at relaxation-mediating endothelial H-1 receptors of the rat aorta (relative potency 556% vs. 100% for histamine) and matched with the functional behaviour of 8a. Agonism observed for each compound was sensitive to blockade by the selective H-1-receptor antagonist mepyramine (pA(2) approximate to 9 (guinea-pig) and pA(2) approximate to 8 (rat aorta)). All histaprodifen analogues 8 stimulated neither histaminergic H-2/H-3, nor cholinergic M-3 receptors. They displayed only low to moderate affinity for these sites (H-2: pD'(2), < 5; H-3/M-3: pA(2) < 6). With regard to the substitution pattern on the benzene ring, there was no correlation between the histaprodifen series and the corresponding derivatives of another selective H-1-receptor agonist, viz. 2-phenylhistamine. (C) 2000 Editions scientifiques et medicales Elsevier SAS.
• 3‘-Chloro-3α-(diphenylmethoxy)tropane But Not 4‘-Chloro-3α- (diphenylmethoxy)tropane Produces a Cocaine-like Behavioral Profile
  作者：Richard H. Kline、Sari Izenwasser、Jonathan L. Katz、David B. Joseph、Wayne D. Bowen、Amy Hauck Newman

  DOI：10.1021/jm950782k

  日期：1997.3.1

  more potent than benztropine and equipotent to or slightly less potent than their previously reported para-substituted homologs in inhibiting [3H]WIN 35,428 binding. However, these same meta-substituted analogs were typically less potent than the 4'-substituted analogs in inhibiting [3H]dopamine uptake. Ortho-substituted analogs were generally less potent in both binding and inhibition of uptake at the

  通常，邻位取代的类似物在结合和抑制多巴胺转运蛋白上的作用均不如苄索平或其他被芳基取代的同系物强。还测试了类似物在去甲肾上腺素和血清素转运蛋白以及毒蕈碱m1受体上的结合。本研究中没有化合物与去甲肾上腺素或5-羟色胺转运蛋白具有高亲和力，但均与毒蕈碱型m1受体具有高亲和力（K1 = 0.41-2.52 nM）。有趣的是，3'-chloro-3α-（二苯基甲氧基）托烷（5c）在受过训练可从盐水中区分10 mg / kg可卡因的动物中产生类似可卡因的作用，不像其4'-Cl同系物和所有先前评估过的苄索平类似物。
• Kinetics of the Solvolyses of Fluoro-Substituted Benzhydryl Derivatives: Reference Electrofuges for the Development of a Comprehensive Nucleofugality Scale
  作者：Christoph Nolte、Herbert Mayr

  DOI：10.1002/ejoc.200901400

  日期：2010.3

  A series of m-fluoro-substituted benzhydryl chlorides, bromides, mesylates, and tosylates 1-X to 5-X were prepared and subjected to solvolysis reactions in various solvents. The observed first-order rate constants k s (25 °C) were found to follow the correlation equation log k s (25 °C) = s f (N f + E f ), which allowed us to determine the electrofugality parameters E f for these destabilized benzhydrylium

  制备了一系列间氟取代的二苯甲基氯化物、溴化物、甲磺酸盐和甲苯磺酸盐 1-X 至 5-X，并在各种溶剂中进行溶剂分解反应。发现观察到的一阶速率常数 ks (25 °C) 遵循相关方程 log ks (25 °C) = sf (N f + E f )，这使我们能够确定这些不稳定的电离参数 E f二苯甲基阳离子和一系列离去基团/溶剂组合的离核参数 N f , sf 。