(S)-4-oxo-1,2,3,4-tetrahydronaphthalen-2-ylmetyl 4-methylbenzenesulfonate | 534599-19-4

• 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)-4-oxo-1,2,3,4-tetrahydronaphthalen-2-ylmetyl 4-methylbenzenesulfonate
• 英文别名: [(2S)-4-oxo-2,3-dihydro-1H-naphthalen-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 534599-19-4
• 化学式: C₁₈H₁₈O₄S
• 分子量: 330.405
• InChiKey: YCNOGGJEPGBYFH-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-氟-3-(哌啶-4-基)苯并[D]异恶唑 、 (S)-4-oxo-1,2,3,4-tetrahydronaphthalen-2-ylmetyl 4-methylbenzenesulfonate 以 N-甲基吡咯烷酮 为溶剂， 生成 (3S)-3-[[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]methyl]-3,4-dihydro-2H-naphthalen-1-one
  参考文献：
  名称：

  Chemoenzymatic synthesis and binding affinity of novel (R)- and (S)-3-aminomethyl-1-tetralones, potential atypical antipsychotics

  摘要：

  A series of (R)- and (S)-3-aminomethyl-1-tetralones, conformationally constrained analogues of haloperidol, have been obtained by enzymatic resolution of the corresponding racemic 3-hydroxymethyl-1-tetralones using Pseudomonasfluorescens lipase. Their binding affinities at dopamine D-2 and serotonin 5-HT2A and 5-HT2C receptors were determined showing in some cases an atypical antipsychotic profile with Meltzer's ratio higher than 1.30. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.064
• 作为产物：
  描述：

  (S)-(+)-1-oxo-1,2,3,4-tetrahydronaphthalen-2-ylmethyl acetate 在 吡啶 、 lithium hydroxide 作用下， 生成 (S)-4-oxo-1,2,3,4-tetrahydronaphthalen-2-ylmetyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Chemoenzymatic synthesis and binding affinity of novel (R)- and (S)-3-aminomethyl-1-tetralones, potential atypical antipsychotics

  摘要：

  A series of (R)- and (S)-3-aminomethyl-1-tetralones, conformationally constrained analogues of haloperidol, have been obtained by enzymatic resolution of the corresponding racemic 3-hydroxymethyl-1-tetralones using Pseudomonasfluorescens lipase. Their binding affinities at dopamine D-2 and serotonin 5-HT2A and 5-HT2C receptors were determined showing in some cases an atypical antipsychotic profile with Meltzer's ratio higher than 1.30. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.064

文献信息

• Preparation of (R)-(−)- and (S)-(+)-3-hydroxymethyl-1-tetralone tosylates, key intermediates in the synthesis of new CNS drugs, via resolution of precursors
  作者：Yolanda Caro、Christian F. Masaguer、Enrique Raviña

  DOI：10.1016/s0957-4166(02)00822-4

  日期：2003.2

  The preparation of (R)-(−)- and (S)-(+)-3-hydroxymethyl-1-tetralone tosylates, key intermediates in the synthesis of new CNS drugs in the aminobutyrophenone family, has been developed via classical resolutions or lipase-catalyzed kinetic resolution of one of their precursors.

  （R）-（-）-和（S）-（+）-3-羟甲基-1-四氢萘基甲苯磺酸酯的制备是通过经典决议或脂肪酶催化其前体之一的动力学拆分。
• Chemoenzymatic synthesis and binding affinity of novel (R)- and (S)-3-aminomethyl-1-tetralones, potential atypical antipsychotics
  作者：Yolanda Caro、Marı́a Torrado、Christian F. Masaguer、Enrique Raviña、Fernando Padı́n、José Brea、Marı́a I. Loza

  DOI：10.1016/j.bmcl.2003.11.064

  日期：2004.2

  A series of (R)- and (S)-3-aminomethyl-1-tetralones, conformationally constrained analogues of haloperidol, have been obtained by enzymatic resolution of the corresponding racemic 3-hydroxymethyl-1-tetralones using Pseudomonasfluorescens lipase. Their binding affinities at dopamine D-2 and serotonin 5-HT2A and 5-HT2C receptors were determined showing in some cases an atypical antipsychotic profile with Meltzer's ratio higher than 1.30. (C) 2003 Elsevier Ltd. All rights reserved.