(trans-2-(4-fluorophenyl)cyclopropyl)methanol | 243665-20-5

• 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: (trans-2-(4-fluorophenyl)cyclopropyl)methanol
• 英文别名: [(1R,2R)-2-(4-fluorophenyl)cyclopropyl]methanol
• CAS: 243665-20-5
• 化学式: C₁₀H₁₁FO
• 分子量: 166.195
• InChiKey: ODPZTCKFPWLUEV-WPRPVWTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (trans-2-(4-fluorophenyl)cyclopropyl)methanol 在 sodium hydride 、 一水合肼 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 20.5h， 生成
  参考文献：
  名称：

  Triazolopyridine ethers as potent, orally active mGlu2 positive allosteric modulators for treating schizophrenia

  摘要：

  Triazolopyridine ethers with mGlu(2) positive allosteric modulator (PAM) activity are disclosed. The synthesis, in vitro activity, and metabolic stability data for a series of analogs is provided. The effort resulted in the discovery of a potent, selective, and brain penetrant lead molecule BMT-133218 ((+)-7m). After oral administration at 10 mg/kg, BMT-133218 demonstrated full reversal of PCP-stimulated locomotor activity and prevented MK-801-induced working memory deficits in separate mouse models. Also, reversal of impairments in executive function were observed in rat set-shifting studies at 3 and 10 mg/kg (p.o.). Extensive plasma protein binding as the result of high lipophilicity likely limited activity at lower doses. Optimized triazolopyridine ethers offer utility as mG1u(2) PAMs for the treatment of schizophrenia and merit further preclinical investigation. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.11.018
• 作为产物：
  描述：

  trans-2-(4-fluorophenyl)cyclopropanecarboxylic acid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以91%的产率得到(trans-2-(4-fluorophenyl)cyclopropyl)methanol
  参考文献：
  名称：

  Picosecond radical kinetics. Rate constants for ring openings of 2-aryl-substituted cyclopropylcarbinyl radicals

  摘要：

  The kinetics of ring openings of a series of eight (trans-2-arylcyclopropyl)methyl radicals (1) were studied by indirect kinetic methods using Barton's PTOC esters as radical precursors and reaction with PhSeH as the competition reaction. The substituents were CF3, F, Me, and OMe located on both the para and meta positions of the aromatic ring. Syntheses of the radical precursors and the products of the radical reactions are described. Kinetics were determined between -43 and 25 degrees C in four cases (CF, and OMe substituents) and at 0 and 25 degrees C in the other four cases. The rate constants at 25 degrees C ranged from 1.0 x 10(11) s(-1) (p-CH3) to 4.1 x 10(11) s(-1) (p-CF,). The relatively large acceleration of the p-CF3 group, ca. 2.5 times as fast as the parent system with Ar = Ph, correlates well with Adam's Delta D substituent parameters but not with other radical substituent parameters. These calibrated radical rearrangements provide a new set of ultrafast reactions that can be applied in mechanistic probe studies.

  DOI：

  10.1139/cjc-77-5-6-1123

文献信息

• Regioselective Brønsted Acid-Catalyzed Annulation of Cyclopropane Aldehydes with <i>N</i>′-Aryl Anthranil Hydrazides: Domino Construction of Tetrahydropyrrolo[1,2-<i>a</i>]quinazolin-5(1<i>H</i>)ones
  作者：Priyanka Singh、Navpreet Kaur、Prabal Banerjee

  DOI：10.1021/acs.joc.9b03170

  日期：2020.3.6

  synthesis of tetrahydropyrrolo[1,2-a]quinazolin-5(1H)one derivatives was achieved by reacting cyclopropane aldehydes with N'-aryl anthranil hydrazides in the presence of p-toluene sulfonic acid (PTSA). The transformation involves domino imine formation and intramolecular cyclization to form 2-arylcyclopropyl-2,3-dihydroquinolin-4(1H)-one, followed by nucleophilic ring opening of the cyclopropyl ring to form

  在对甲苯磺酸（PTSA）存在下，通过使环丙烷醛与N'-芳基邻氨基苯甲酰肼反应，可以实现对四氢吡咯并[1,2-a]喹唑啉-5（1H）酮衍生物的高度区域选择性合成。该转化涉及多米诺亚胺的形成和分子内环化以形成2-芳基环丙基-2,3-二氢喹啉-4（1H）-一个，然后环丙基环的亲核开环形成所需的四氢吡咯并[1,2-a]喹唑啉- 5（1H）1具有良好的收率，并且具有完全的区域选择性。该方案可耐受多种官能团，因此为吡咯并喹唑啉酮的合成提供了一种简单而高效的方法。
• Donor–Acceptor Bicyclopropyls as 1,6-Zwitterionic Intermediates: Synthesis and Reactions with 4-Phenyl-1,2,4-triazoline-3,5-dione and Terminal Acetylenes
  作者：Konstantin V. Potapov、Dmitry A. Denisov、Valeriia V. Glushkova、Roman A. Novikov、Yury V. Tomilov

  DOI：10.1021/acs.joc.0c02293

  日期：2020.12.4

  the presence of Lewis acids was used as a synthetic equivalent of 1,6-zwitterions. Opening of both cyclopropane rings in 2′-aryl-1,1′-bicyclopropyl-2,2-dicarboxylates (D–A bicyclopropyl, ABCDs) in the presence of GaI3 + Bu4N+GaI4– results in 5-iodo-5-arylpent-2-enylmalonates as products of HI formal 1,6-addition to the bicyclopropyl system. The use of GaCl3 or GaBr3 as a Lewis acid and terminal aryl

  通过在路易斯酸存在下结合供体基团和受体基团而活化的双环丙基体系被用作1,6-两性离子的合成等价物。在存在GaI 3 + Bu 4 N + GaI 4的情况下，在2'-芳基-1,1'-双环丙基-2,2-二羧酸酯（DA双环丙基，ABCD）中打开两个环丙烷环–产生5-碘-5-芳基戊二烯基丙二酸酯作为双环丙基系统中HI正式1，6-加成的产物。使用GaCl 3或GaBr 3作为路易斯酸，如末端的芳基或烷基乙炔作为1，6-两性离子拦截剂，可使烷基取代基生长，得到相应的无环7-氯（溴）-庚-2,6-二烯基丙二酸酯。Yb（OTf）3催化ABCD与4-苯基-1,2,4-三唑啉-3,5-二酮（PTAD）的反应也导致两个环丙烷环的打开。反应产物是四氢哒嗪衍生物-（7,9-二氧代-1,6,8-三氮杂双环[4.3.0]非-3-烯-2-基甲基）丙二酸酯-在丙二酸基团中包含一个以上的PTAD部分。
• Lewis Acid Catalyzed Annulation of Cyclopropane Carbaldehydes and Aryl Hydrazines: Construction of Tetrahydropyridazines and Application Toward a One-Pot Synthesis of Hexahydropyrrolo[1,2-<i>b</i>]pyridazines
  作者：Raghunath Dey、Pankaj Kumar、Prabal Banerjee

  DOI：10.1021/acs.joc.8b00332

  日期：2018.5.18

  In this report, a facile synthesis of tetrahydropyridazines via a Lewis acid catalyzed annulation reaction of cyclopropane carbaldehydes and aryl hydrazines has been demonstrated. Moreover, the generated tetrahydropyridazine further participated in a cycloaddition reaction with donor–acceptor cyclopropanes to furnish hexahydropyrrolo[1,2-b]pyridazines. We also performed these two steps in one pot in

  在该报告中，已经证明了通过路易斯酸催化的环丙烷甲醛和芳基肼的环合反应可轻松合成四氢哒嗪。此外，生成的四氢哒嗪进一步与供体-受体环丙烷一起参与环加成反应，提供六氢吡咯并[1,2- b ]哒嗪。我们还在一个锅中以连续的方式执行了这两个步骤。另外，六氢吡咯并[1,2- b ]哒嗪的单脱羧反应得到了良好的收率。
• Metal-free domino Cloke-Wilson rearrangement-hydration-dimerization of cyclopropane carbaldehydes: A facile access to oxybis(2-aryltetrahydrofuran) derivatives
  作者：Raghunath Dey、Shruti Rajput、Prabal Banerjee

  DOI：10.1016/j.tet.2020.131080

  日期：2020.4

  demonstrated a metal-free transformation of cyclopropane carbaldehydes to oxybis(2-aryltetrahydrofuran) derivatives via a domino Cloke-Wilson rearrangement-hydration-dimerization sequence. Commercially inexpensive p-toluene sulfonic acid (PTSA) was used as a Brønsted acid catalyst, and reactions were conducted in an open-flask. Detection of reaction intermediates were carried to get an insight into the

  在这项工作中，我们已经证明了通过多米诺克Cloke-Wilson重排-水合-二聚序列将环丙烷甲醛无金属转化为双（2-芳基四氢呋喃）衍生物。商业上便宜的对甲苯磺酸（PTSA）被用作布朗斯台德酸催化剂，并且反应在开瓶中进行。进行反应中间体的检测以深入了解反应途径。
• Exploitation of Cyclopropane Carbaldehydes to Prins Cyclization: Quick Access to (<i>E</i>)-Hexahydrooxonine and Octahydrocyclopenta[<i>b</i>]pyran
  作者：Pankaj Kumar、Raghunath Dey、Prabal Banerjee

  DOI：10.1021/acs.orglett.8b02094

  日期：2018.9.7

  route, augmented by another cyclization within a nine-membered ring to afford a bicyclized product (4,4-dihalo-5-aryloctahydrocyclopenta[b]pyran). Easy transformation of the resulting geminal dihalide to a vinyl halide and a ketone further supplemented the substance of this approach.

  报道了用3-丁烯-1-醇对环丙烷甲醛的单步TiX 4介导的Prins型环化反应，以相对立体地构建相对应变的（E）-六氢氧代肟酸酯。将醇转换为3-butyn-1-ol引发了类似的路线，并在九元环内进行了另一个环化反应，从而得到了双环化产物（4,4-二卤代5-芳基氢环戊[ b ]吡喃）。容易将生成的二卤代双卤化物转化为乙烯基卤化物和酮，进一步补充了这种方法的实质。