(1R,4S,6S)-4-benzhydryl-3,7-dioxabicyclo[4.1.0]heptane | 862647-19-6

• 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: (1R,4S,6S)-4-benzhydryl-3,7-dioxabicyclo[4.1.0]heptane
• 英文别名: (1R,4S,6S)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]-heptane
• CAS: 862647-19-6
• 化学式: C₁₈H₁₈O₂
• 分子量: 266.34
• InChiKey: DUEQWSFFKLBHLL-YESZJQIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,4S,6S)-4-benzhydryl-3,7-dioxabicyclo[4.1.0]heptane 、 4-甲氧基苄胺 以 甲醇 为溶剂， 以to yield (3R,4R,6S)-6-benzhydryl-4-(4-methoxy-benzylamino)-tetrahydropyran-3-ol, (−)-29g 0.02 g (63%, [α]D=(−)63.75, c=1, MeOH)的产率得到(3R,4R,6S)-6-benzhydryl-4-(4-methoxy-benzylamino)-tetrahydropyran-3-ol
  参考文献：
  名称：

  TRI-SUBSTITUTED 2-BENZHYDRYL-5-BENZYLAMINO-TETRAHYDRO-PYRAN-4-OL AND 6-BENZHYDRYL-4-BENZYLAMINO-TETRAHYDRO-PYRAN-3-OL ANALOGUES, AND NOVEL 3,6-DISUBSTITUTED PYRAN DERIVATIVES

  摘要：

  新型3,6-二取代吡喃，可选在4位进一步取代，是单胺再摄取抑制剂，具有抗抑郁药物的活性特征。

  公开号：

  US20140058120A1
• 作为产物：
  描述：

  (2R)-2-benzhydryloxirane 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 copper(l) iodide 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 43.0h， 生成 (1R,4S,6S)-4-benzhydryl-3,7-dioxabicyclo[4.1.0]heptane
  参考文献：
  名称：

  Discovery of Novel Trisubstituted Asymmetric Derivatives of (2S,4R,5R)-2-benzhydryl-5-benzylaminotetrahydropyran-4-ol, Exhibiting High Affinity for Serotonin and Norepinephrine Transporters in a Stereospecific Manner

  摘要：

  In our structure-activity relationship study on 3,6-disubstituted pyran derivatives, we have carried out asymmetric synthesis and biological characterization of trisubstituted (2S,4R,5R)-2-benzhydryl-5-benzylaminotetrahydropyran-4-ol and (3S,4R,6S)-6-benzhydryl-4-benzylaminotetrahydropyran-3-ol derivatives and their enantiomers. All synthesized derivatives were tested for their affinities for the dopamine transporter (DAT), serotonin transporter (SERT), and norepinephrine transporter (NET) in the brain by measuring their potency in inhibiting the uptake of [H-3]DA, [H-3]-5-HT, and [3H]NE, respectively. Compounds were also tested for their binding affinity at the DAT by their inhibition of [H-3]WIN 35,428. Biological results indicated that regioselectivity and stereoselectivity played important roles in determining activity for monoamine transporters as only (-)-isomers of 2-benzhydryl-5-benzylaminotetrahydropyran-4-ol derivatives exhibited appreciable potency for the monoamine transporters, in particular for the SERT and NET. Among the active analogues, (-)-9d exhibited potent and selective affinity at the NET (K-i, [H-3]NE = 4.92 nM; DAT/NET = 91 and SERT/NET = 140). One of the derivatives with p-methoxybenzyl substitution, (-)-9a, was potent at both SERT and NET (Ki, [3H]-5-HT = 25.9 and [3H]NE = 15.8 nM, respectively). In the active analogue series ((-)-9a-(-)-9e), a cis-relationship between the biphenyl and the amino moiety was maintained for the SERT and NET interactions, as was observed with our earlier 3,6-disubstituted pyran compounds for the DAT interaction. To the best of our knowledge, this current series of compounds represents a novel class of pyran derivatives as blockers for monoamine transporters.

  DOI：

  10.1021/jm049021k
• 作为试剂：
  描述：

  (2S)-2-benzhydryl-3,6-dihydro-2H-pyran 、 间氯过氧苯甲酸 、 Disodium;sulfite 在 氮气 、 二氯甲烷 、 碳酸氢钠 、 Brine 、 Sodium sulfate-III 、 crude products 、 silica gel 、 hexane-diethyl ether 、 (1R,4S,6S)-4-benzhydryl-3,7-dioxabicyclo[4.1.0]heptane 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以to give 0.08 g (1S,4S,6R)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]-heptane 28a (50.3%, [α]D=(−)60, c=1, MeOH) and 0.065 g 28b (1R,4S,6S)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]-heptane (41%, [α]D=(−)76, c=1, MeOH)的产率得到(1S,4S,6R)-4-benzhydryl-3,7-dioxabicyclo[4.1.0]heptane
  参考文献：
  名称：

  TRI-SUBSTITUTED 2-BENZHYDRYL-5-BENZYLAMINO-TETRAHYDRO-PYRAN-4-OL AND 6-BENZHYDRYL-4-BENZYLAMINO-TETRAHYDRO-PYRAN-3-OL ANALOGUES, AND NOVEL 3,6-DISBUSTITUTED PYRAN DERIVATIVES

  摘要：

  Novel 3,6-二取代吡喃，其在4-位置可能具有进一步取代基团，是单胺再摄取抑制剂，具有抗抑郁药的活性特征。

  公开号：

  US20100280091A1

文献信息

• [EN] TRI-SUBSTITUED 2-BENZHYDRYL-5-BENZLAMINO-TETRAHYDRO-PYRAN-4-OL AND 6-BENZHYDRYL-4-BENZYLAMINO-TETRAHYDRO-PYRAN-3-OL ANALOGUES, AND NOVEL 3,6-DISUBSTITUTED PYRAN DERIVATIVES<br/>[FR] À TROIS SUBSTITUT 2-BENZHYDRYL-5- BENZLAMINO- TÉTRAHYDROPYRAN-4-OL ET 6-BENZHYDRYL-4-BENZYLAMINO-ANALOGUES TÉTRAHYDROPYRAN-3-OL ET NOUVEAUX DÉRIVÉS PYRANNE DISUBSTITUÉ 3,6
  申请人：UNIV WAYNE STATE

  公开号：WO2005105075A1

  公开（公告）日：2005-11-10

  Novel 3,6-disubstituted pyrans, optionally with a further substituent at the 4-position, are monoamine reuptake inhibitors with activity profiles of anti- depressants.

  小说3,6-二取代吡喃，可选地在4-位置进一步取代，是具有抗抑郁活性剖面的单胺再摄取抑制剂。
• Tri-substituted 2-benzhydryl-5-benzlamino-tetrahydro-pyran-4-ol and 6-benzhydryl-4-benzylamino-tetrahydro-pyran-3-ol analogues, and novel 3,6-disubstituted pyran derivatives
  申请人：Dutta K. Aloke

  公开号：US20060122263A1

  公开（公告）日：2006-06-08

  Novel 3,6-disubstituted pyrans, optionally with a further substituent at the 4-position, are monoamine reuptake inhibitors with activity profiles of anti-depressants.

  小说3,6-二取代吡喃，可在4位进一步取代，是单胺再摄取抑制剂，具有抗抑郁药的活性特征。
• TRI-SUBSTITUED 2-BENZHYDRYL 5-BENZLAMINO-TETRAHYDRO-PYRAN-4-OL AND 6-BENZHYDRYL-4-BENZYLAMINO-TETRAHYDRO-PYRAN-3-OL ANALOGUES, AND NOVEL 3,6 DISUBSTITUTED PYRAN DERIVATIVES
  申请人：Dutta K. Aloke

  公开号：US20070276005A1

  公开（公告）日：2007-11-29

  Novel 3,6-disubstituted pyrans, optionally with a further substituent at the 4-position, are monoamine reuptake inhibitors with activity profiles of anti-depressants.

  小说3,6-二取代吡喃，可以在4-位置进一步取代，是单胺再摄取抑制剂，具有抗抑郁药的活性特征。
• Tri-Substituted 2-Benzhydryl-5-Benzlamino-Tetrahydro-Pyran-4-OL and 6-Benzhydryl-4-Benzylamino-Tetrahydro-Pyran-3-OL Analogues, and Novel 3,6-Disubstituted Pyran Derivatives
  申请人：Dutta Aloke K.

  公开号：US20080167478A1

  公开（公告）日：2008-07-10

  Novel 3,6-disubstituted pyrans, optionally with a further substituent at the 4-position, are monoamine reuptake inhibitors with activity profiles of anti-depressants.

  小说3,6-二取代吡喃，可在4位进一步取代，是单胺再摄取抑制剂，具有抗抑郁药的活性特征。
• Tri-substituted 2-benzhydryl 5-benzlamino-tetrahydro-pyran-4-OL and 6-benzhydryl-4-benzylamino-tetrahydro-pyran-3-OL analogues, and novel 3,6 disubstituted pyran derivatives
  申请人：Wayne State University

  公开号：US07915433B2

  公开（公告）日：2011-03-29

  Novel 3,6-disubstituted pyrans, optionally with a further substituent at the 4-position, are monoamine reuptake inhibitors with activity profiles of anti-depressants.

  Novel 3,6-二取代吡喃，可选在4位进一步取代的化合物，是单胺再摄取抑制剂，并具有抗抑郁活性。