(4-氯苯基)-二苯基甲醇 | 6922-89-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: (4-氯苯基)-二苯基甲醇
• 中文别名: 克霉唑杂质
• 英文名称: p-chlorotriphenylmethanol
• 英文别名: (4-chlorophenyl)diphenylmethanol；4-Chlor-triphenylcarbinol；NSC 20739；(4-Chlorophenyl)(diphenyl)methanol；(4-chlorophenyl)-diphenylmethanol
• CAS: 6922-89-0
• 化学式: C₁₉H₁₅ClO
• 分子量: 294.78
• InChiKey: KHVJXWFCBMQXLH-UHFFFAOYSA-N

物化性质

• 熔点：
  85 °C
• 沸点：
  440.5±40.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)
• 溶解度：
  溶于二氯甲烷、乙醇、乙酸乙酯、四氢呋喃

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  (4-氯苯基)-二苯基甲醇 在 乙酰氯 作用下， 以 甲苯 、 苯 为溶剂， 反应 1.5h， 生成 4-chlorotriphenylacetonitrile oxide
  参考文献：
  名称：

  A kinetic study of the rearrangement of triarylacetonitrile oxides

  摘要：

  The thermal rearrangement of triphenylacetonitrile oxide (1a) to triphenylmethyl isocyanate (2) is a first-order process. Rate constants at five temperatures between 116 and 190-degrees-C were determined giving DELTA-H double-ended dagger = 9.3 +/- 1.1 kcal/mol and DELTA-S double-ended dagger = -58.2 +/- 2.4 cal/mol.K. The rearrangement of substituted triarylacetonitrile oxides (1b-d) occur only slightly faster than that of 1a. These results are interpreted in terms of a concerted single-step rearrangement in which the highly ordered transition state (6c) has a degree of radical character.

  DOI：

  10.1021/jo00026a024
• 作为产物：
  描述：

  4-氯三氯甲苯 在 sodium hydroxide 、 三氯化铝 作用下， 以 乙腈 为溶剂， 反应 28.0h， 生成 (4-氯苯基)-二苯基甲醇
  参考文献：
  名称：

  Tritylamino Aromatic Heterocycles and Related Carbinols as Blockers of Ca 2+-Activated Potassium Ion Channels Underlying Neuronal Hyperpolarization

  摘要：

  A series of novel aromatic tritylamino heterocycles has been synthesized and the compounds have been tested in comparison with clotrimazole for their ability to inhibit the slow afterhyperpolarization current (sI(AHP)) in cultured rat hippocampal pyramidal neurones. Some analogues of the clotrimazole metabolite, 2-chlorophenyl-diphenyl methanol, having different chlorination substitution in the triphenyl group have also been examined. Two compounds in particular, 3-[(2-chlorophenyl)-diphenylmethylamino]pyridine (3a, UCL 1880) and 2-tritylaminothiazole (6, UCL 2027), are of special interest; they are effective blockers of the sI(AHP) (IC50 = 1.1-1.2 muM) and are much more selective than clotrimazole since they have less effect on the high voltage-activated Ca2+ current.

  DOI：

  10.1002/1521-4184(200204)335:4<159::aid-ardp159>3.0.co;2-k

文献信息

• An Efficient Ga(OTf)₃/Isopropanol Catalytic System for Direct Reduction of Benzylic Alcohols
  作者：Masahiro Sai

  DOI：10.1002/adsc.201801135

  日期：2018.11.16

  first gallium‐catalyzed direct reduction of benzylic alcohols using isopropanol as a reductant. The reaction proceeds via gallium catalyst‐assisted hydride transfer of the in situ‐generated benzylic isopropyl ether. The method generates only water and acetone as byproducts and thus provides an atom‐economic and environmentally friendly approach to the synthesis of di‐ and triarylmethanes, which are important

  这项研究旨在报告使用异丙醇作为还原剂的镓催化的首次直接还原苄醇。反应通过原位生成的苄基异丙醚的镓催化剂辅助氢化物转移而进行。该方法仅产生副产物水和丙酮，因此为二芳基甲烷和三芳基甲烷的合成提供了一种原子经济且环保的方法，而二芳基甲烷和三芳基甲烷是各种生物活性化合物和功能材料中的重要子结构。
• Steric and Electronic Effects Influencing β-Aryl Elimination in the Pd-catalyzed Carbon–Carbon Single Bond Activation of Triarylmethanols
  作者：James R. Bour、Jacob C. Green、Valerie J. Winton、Jeffrey B. Johnson

  DOI：10.1021/jo302592g

  日期：2013.2.15

  An analysis of the palladium-catalyzed activation of carbon–carbon single bonds within triarylmethanols has led to a greater understanding of factors influencing the β-aryl elimination process responsible for C–C bond cleavage. A series of competition reactions were utilized to determine that β-aryl elimination of aryl substituents containing ortho-substitution proceeds with significant preference

  对钯催化的三芳基甲醇中碳-碳单键活化的分析，导致人们对影响影响C-C键断裂的β-芳基消除过程的因素有了更深入的了解。利用一系列竞争反应来确定β-芳基消除含有邻位取代基的芳基取代基比未取代的苯环显着地优先进行。进一步的实验表明，与相对中性的物质相比，含有强供体或撤离取代基的底物更容易从三芳基甲醇中裂解出来。
• Reactivities of triarylmethyl and diarylmethyl cations with azide ion investigated by laser flash photolysis. Diffusion-controlled reactions
  作者：Robert A. McClelland、V. M. Kanagasabapathy、Narinder S. Banait、Steen Steenken

  DOI：10.1021/ja00003a040

  日期：1991.1

  By use of the technique of laser flash photolysis, rate constants k AZ and k S have been directly measured for the reactions at 20 o C in acetonitrile-water (AN-W) solutions of varying composition of 18 triarylmethyl and 10 diarylmethyl cations with azide and solvent. The cations have k S that depend on substituent and vary from ∼10 1 to ∼10 7 s −1 . For the more stable ions k AZ also varies, increasing

  通过使用激光闪光光解技术，已经直接测量了在 20 o C 下在 18 个三芳基甲基和 10 个二芳基甲基阳离子与叠氮化物的不同组成的乙腈-水 (AN-W) 溶液中反应的速率常数 k AZ 和 k S和溶剂。阳离子具有取决于取代基的k S 并且从～10 1 到～10 7 s -1 变化。对于更稳定的离子，k AZ 也发生变化，随着给电子量的减少而增加，并且随着乙腈含量的增加而增加多达10 3 。然而，对于不太稳定的阳离子，速率常数与取代基无关
• Kinetic Study of the Reaction between Substituted Triphenylmethyl Perchlorates with Pyridines in Nitromethane and 1,2-Dichloroethane Solvents
  作者：Chang B. Kim、Kenneth T. Leffek

  DOI：10.1139/v75-487

  日期：1975.11.15

  Second-order rate constants at 25 °C have been measured for the reaction of triphenylmethyl carbonium ion with pyridine and substituted pyridines in nitromethane and 1,2-dichloroethane solvent. The...

  在硝基甲烷和 1,2-二氯乙烷溶剂中，三苯基甲基碳正离子与吡啶和取代吡啶反应的二级速率常数已在 25 °C 下进行测量。这...
• 1-(3,3,3-Triarylalkyl)-4-phenyl-piperidinealkanols
  申请人：G. D. Searle & Co.

  公开号：US04072686A1

  公开（公告）日：1978-02-07

  The present invention encompasses compounds of the formula ##STR1## and pharmaceutically acceptable acid addition salts thereof wherein the Alk is straight or branched chain alkylene containing 2-4 carbon atoms; M is alkylene having 1-4 carbon atoms; Ar and Ar' are phenyl, alkyl substituted phenyl wherein the alkyl contains from 1-4 carbon atoms or halo substituted phenyl; Ar" is phenyl, alkyl substituted phenyl wherein the alkyl contains 1-4 carbon atoms, halo substituted phenyl or pyridyl; X is hydrogen, halogen, trifluoromethyl or alkyl having from 1-4 carbon atoms; R is hydrogen alkyl having from 1-7 carbon atoms or an alkanoyl having from 2-5 carbon atoms. These compounds are potent antidiarrheal agents characterized by little, if any, central nervous system activity.

  本发明涵盖了以下结构的化合物##STR1##及其药学上可接受的酸盐，其中Alk是含有2-4个碳原子的直链或支链烷基; M是含有1-4个碳原子的烷基; Ar和Ar'是苯基，烷基取代的苯基，其中烷基含有1-4个碳原子或卤素取代的苯基; Ar"是苯基，烷基取代的苯基，其中烷基含有1-4个碳原子，卤素取代的苯基或吡啶基; X是氢，卤素，三氟甲基或含有1-4个碳原子的烷基; R是氢，含有1-7个碳原子的烷基或含有2-5个碳原子的烷酰基。这些化合物是具有很少或没有中枢神经系统活性的强效止泻剂。