(-)-(S)-1-fluoro-3-<(4-methylphenyl)sulphinyl>-2-propanone | 142722-58-5

• 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: (-)-(S)-1-fluoro-3-<(4-methylphenyl)sulphinyl>-2-propanone
• 英文别名: (S)-(-)-1-fluoro-3-<(4-methylphenyl)sulphinyl>propan-2-one；(-)-(S)-1-fluoro-3-<(4-methylphenyl)sulfinyl>propan-2-one；(S_S)-3-fluoro-1-[(4-methylphenyl)sulfinyl]propan-2-one；(S)-1-fluoro-3-(4-methylphenylsulphinyl)propan-2-one；(S)-3-Fluoro-1-(4-methylphenyl)sulfinylacetone；(S)-(-)-1-fluoro-3-[(4-methylphenyl)sulphinyl]propan-2-one；1-fluoro-3-[(S)-(4-methylphenyl)sulfinyl]propan-2-one
• CAS: 142722-58-5
• 化学式: C₁₀H₁₁FO₂S
• 分子量: 214.261
• InChiKey: RLMFLTGCKDDHDC-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-(S)-1-fluoro-3-<(4-methylphenyl)sulphinyl>-2-propanone 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.08h， 以91%的产率得到(2R)-1-fluoro-3-<(S)-(4-methylphenyl)sulphinyl>propan-2-ol
  参考文献：
  名称：

  Cavicchio, Giancarlo; Marchetti, Valeria; Arnone, Alberto, Gazzetta Chimica Italiana, 1990, vol. 120, p. 741 - 747

  摘要：

  DOI：
• 作为产物：
  描述：

  4-Methyl-benzenesulfinic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 在 lithium diisopropyl amide 作用下， 反应 0.08h， 生成 (-)-(S)-1-fluoro-3-<(4-methylphenyl)sulphinyl>-2-propanone
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of enantiomerically pure 4-deoxy-4-fluoromuscarines

  摘要：

  Four isomers of [(4-fluoro-5-methyl-tetrahydrofuran-2-yl)methyl]trimethylammonium iodide (4-deoxy-4-fluoro-muscarines) were prepared in enantiomerically and diastereomerically pure form from (S)-(-)-methyl 4-methylphenyl sulfoxide, ethyl fluoroacetate, and allyl bromide. Their absolute configurations were assigned by H-1 NMR analyses. The four optically pure compounds were tested in vitro on guinea pig and their muscarinic potency was evaluated at M3 (ileum and bladder) and M2 (heart) muscarinic receptor subtypes. Compound 1a, the most potent isomer of the series, was also tested in vivo on pithed rat and its muscarinic activity at the M1 receptor subtype was compared with that of muscarine. Moreover, affinity and relative efficacy were calculated in vitro for this compound at M2 (heart force and rate) and M3 (ileum and bladder) receptors in order to investigate muscarinic receptor heterogeneity. The 4-deoxy-4-fluoromuscarines display a similar trend of potency as the corresponding muscarines and compound 1a shows differences in the affinity constants among the studied tissues. Replacement of a hydroxyl group for a fluorine atom in the 4 position of muscarine produces 1 order of magnitude increase in affinity for cardiac M2 muscarinic receptors controlling rate, while the affinity at cardiac M2 muscarinic receptors controlling force is unchanged, opening the possibility of a further classification of cardiac muscarinic receptors.

  DOI：

  10.1021/jm00095a003

文献信息

• A new versatile fluorinated C4 chiron
  作者：Alberto Arnone、Pierfrancesco Bravo、Giancarlo Cavicchio、Massimo Frigerio、Valeria Marchetti、Fiorenza Viani、Carmela Zappalà

  DOI：10.1016/s0040-4039(00)61160-7

  日期：1992.9

  Optically pure 2-(fluoromethyl)-2-[(4-methylphenylsulphinyl)methyl]oxirane has been obtained in good yield and with high d.e. by reacting diazomethane with optically pure 1-fluoro-3-(4-methylphenylsulphinyl)propan-2-one. Regio- and stereo-selective openings of oxirane ring performed with selected nucleophiles afforded several useful derivatives.

  通过使重氮甲烷与光学纯的1-氟-3-（4-甲基苯基亚磺酰基）丙烷-2-反应，以高收率和高脱除率获得光学纯的2-（氟甲基）-2-[（4-甲基苯基亚磺酰基）甲基]环氧乙烷。一。用选定的亲核试剂进行的环氧乙烷环的区域和立体选择性开环提供了几种有用的衍生物。
• Synthesis of 2-Fluoro Analogues of Frontalin
  作者：Pierfrancesco Bravo、Massimo Frigerio、Taizo Ono、Walter Panzeri、Cristina Pesenti、Akiko Sekine、Fiorenza Viani

  DOI：10.1002/(sici)1099-0690(200004)2000:8<1387::aid-ejoc1387>3.0.co;2-g

  日期：2000.4

  The synthesis of enantiomerically and diastereomerically pure (−)-(1R,2R,5R)- and (−)-(1R,2S,5R)-2-fluoro frontalin (7) starting from (+)-(1S)-menthyl-(R)-toluene-4-sulfinate, methylmagnesium bromide, methyl fluoroacetate, 4-pentenyl bromide and diazomethane is described. The absolute stereochemistry was unambiguously determined by X-ray analysis of (+)-(1S,2R,5S,RS)-5, an intermediate in the synthesis

  以 (+)-(1S)-薄荷基为原料合成对映体和非对映体纯的 (-)-(1R,2R,5R)- 和 (-)-(1R,2S,5R)-2-fluorofrontalin (7)描述了-(R)-甲苯-4-亚磺酸盐、甲基溴化镁、氟乙酸甲酯、4-戊烯基溴和重氮甲烷。通过 (+)-(1S,2R,5S,RS)-5 的 X 射线分析明确确定绝对立体化学，这是合成对映体 (+)-(1S,2R,5S)-2- 的中间体氟前蛋白 (7)。
• Stereoselective Synthesis of Trifluoro- and Monofluoro-Analogues of Frontalin and Evaluation of Their Biological Activity
  作者：Paolo Ambrosi、Alberto Arnone、Pierfrancesco Bravo、Luca Bruché、Antonio De Cristofaro、Valeria Francardi、Massimo Frigerio、Enzo Gatti、Giacinto S. Germinara、Walter Panzeri、Fabrizio Pennacchio、Cristina Pesenti、Giuseppe Rotundo、Pio F. Roversi、Cristina Salvadori、Fiorenza Viani、Matteo Zanda

  DOI：10.1021/jo0055640

  日期：2001.12.1

  stereoselective synthesis of both enantiomers of trifluoro frontalin (-)-(1S,5R)- and (+)-(1R,5S)-8, as well as of diastereomeric monofluoro frontalines (-)-(1R,2R,5R)-18 and (-)-(1R,2S,5R)-20, analogues of the bioactive component of the aggregation pheromone of the Scolytidae insect family, has been accomplished starting from (-)-(1R)- and (+)-(1S)-menthyl (S)-toluene-4-sulfinate as a source of chirality and

  立体选择性合成三氟额叶蛋白（-）-（1S，5R）-和（+）-（1R，5S）-8的对映异构体以及非对映体单氟额叶碱（-）-（1R，2R，5R） -18和（-）-（1R，2S，5R）-20是鞘翅目昆虫家族聚集信息素生物活性成分的类似物，从（-）-（1R）-和（+）- （1S）-薄荷基（S）-甲苯-4-亚磺酸盐作为手性来源，三氟乙酸甲酯或氟乙酸甲酯分别作为氟来源。C-1立体中心是通过重氮甲烷将β-亚磺酰基酮2和13进行立体选择性环氧化而安装的。双环核是通过完全立体控制和化学选择性串联的Wacker氧化/中间不饱和亚磺酰基二醇5、15和19的分子内缩酮化而获得的。在实验室测试中，轴向氟化（-）-20引发了对Dendroctonus micans雌性女性的强电响应，而赤道氟化（-）-18和三氟类似物（-）-8则显示了适度的响应。由于（D）micans局部稀少，使用（-）-20进行的田间试验没有指示性，但对其他鞘翅目科显示出一定的吸引力。
• Synthesis of enantiomerically pure 3-fluoromethylthreonines from (S)-1-fluoro-3-tolylsulfinylacetone
  作者：Alberto Arnone、Detlef Gestmann、Stefano Valdo Meille、Giuseppe Resnati、Giancarlo Sidoti

  DOI：10.1039/cc9960002569

  日期：——

  The copper(I) catalysed aldol reaction between methyl isocyanoacetate and (S)-3-fluoro-1-(4-methylphenyl)-sulfinylacetone affords oxazoline products which, after diastereoisomer separation, give in high yields optically pure 3-fluoromethylthreonine analogues whose absolute and relative configurations have been assigned through X-ray analyses.

  异氰基乙酸甲酯与(S)-3-氟-1-(4-甲基苯基)-亚磺酰基丙酮在铜(I)催化下发生醛醇反应，生成噁唑啉产物，经非对映异构体分离后，可得到高产率的光学纯 3-氟甲基苏氨酸类似物，这些类似物的绝对构型和相对构型已通过 X 射线分析确定。
• [EN] ETHYNYLBENZENE DERIVATIVES<br/>[FR] DÉRIVÉS D'ÉTHYNYLE BENZÈNE
  申请人：UNIV DUKE

  公开号：WO2012031298A3

  公开（公告）日：2012-09-27