(3R)-3-(羟基甲基)-3,4-二氢-1(2H)-萘酮 | 534599-18-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: (3R)-3-(羟基甲基)-3,4-二氢-1(2H)-萘酮
• 英文名称: (R)-(-)-3-hydroxymethyl-1,2,3,4-tetrahydronaphthalen-1-one
• 英文别名: (R)-3-(hydroxymethyl)-1,2,3,4-tetrahydronaphthalen-1-one；(R)-3-(Hydroxymethyl)-3,4-dihydronaphthalen-1(2H)-one；(3R)-3-(hydroxymethyl)-3,4-dihydro-2H-naphthalen-1-one
• CAS: 534599-18-3
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: CREVFIPIRJCEIY-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R)-3-(羟基甲基)-3,4-二氢-1(2H)-萘酮 在 吡啶 作用下， 以 N-甲基吡咯烷酮 为溶剂， 生成 (3R)-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：

  2-苄基丁二酸 在 吡啶 、 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 乙酸乙烯酯 、 pseudomonas fluorescens lipase 、 硫酸 、 乙酸酐 作用下， 以 乙醚 、 氯仿 、 苯 为溶剂， 反应 35.5h， 生成 (3R)-3-(羟基甲基)-3,4-二氢-1(2H)-萘酮
  参考文献：
  名称：

  （R）-（-）-和（S）-（+）-3-羟甲基-1-四氢萘酮甲苯磺酸盐的制备，这些化合物是通过拆分前体来合成新的中枢神经系统药物的关键中间体

  摘要：

  （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。

  DOI：

  10.1016/s0957-4166(02)00822-4

文献信息

• Kinetic resolution of 3-hydroxymethylbenzocycloalkanols by selective asymmetric hydrogen-transfer oxidation
  作者：Yolanda Caro、Marı́a Torrado、Christian F. Masaguer、Enrique Raviña

  DOI：10.1016/j.tetasy.2003.08.016

  日期：2003.11

  Kinetic resolution of 3-hydroxymethylbenzocycloalkanols was performed by selective asymmetric hydrogen-transfer oxidation using the Ru(II)-(S,S)-TsDPEN catalyst. Thus, several 3-hydroxymethyl-1-tetralols 7a-d afforded (1R,3R)-3-hydroxymethyl-1-tetralols (1R,3R)-7a-d and (S)-3-hydroxymethyl-1-tetralones (S)-9a-d, and 3-hydroxymethyl-1-indanol 7e gave (1R,3S)3-hydroxymethyl-1-indanol (1R,3S)-7e and (R)-3-hydroxymethyl-1-indanone (R)-9e, with high enantioselectivities. (C) 2003 Elsevier Ltd. All rights reserved.
• 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.