(S)-3-(hydroxymethyl)-6-methoxy-1,2,3,4-tetrahydronaphthalen-1-one | 651013-82-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (S)-3-(hydroxymethyl)-6-methoxy-1,2,3,4-tetrahydronaphthalen-1-one
• 英文别名: (3S)-3-(Hydroxymethyl)-6-methoxy-3,4-dihydronaphthalen-1(2H)-one；(3S)-3-(hydroxymethyl)-6-methoxy-3,4-dihydro-2H-naphthalen-1-one
• CAS: 651013-82-0
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: SNLFPIXTPYNYRQ-QMMMGPOBSA-N

物化性质

• 熔点：
  70-72 °C
• 沸点：
  392.8±35.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-(hydroxymethyl)-6-methoxy-1,2,3,4-tetrahydronaphthalen-1-one 在 吡啶 作用下， 以 N-甲基吡咯烷酮 为溶剂， 生成 (3S)-3-[[4-(4-fluorobenzoyl)piperidin-1-yl]methyl]-6-methoxy-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：

  Acetic acid (S)-7-methoxy-4-oxo-1,2,3,4-tetrahydro-naphthalen-2-ylmethyl ester 在 lithium hydroxide 作用下， 以90%的产率得到(S)-3-(hydroxymethyl)-6-methoxy-1,2,3,4-tetrahydronaphthalen-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

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.
• 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.