(+/-)-1,2,3,4-tetrahydro-5-methoxy-2-oxo-1-(2-propenyl)naphthalene | 134465-79-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (+/-)-1,2,3,4-tetrahydro-5-methoxy-2-oxo-1-(2-propenyl)naphthalene
• 英文别名: 1,2,3,4-Tetrahydro-5-methoxy-2-oxo-1-(2-propenyl)-naphthalene；1-Allyl-5-methoxy-tetralon-2；5-methoxy-1-prop-2-enyl-3,4-dihydro-1H-naphthalen-2-one
• CAS: 134465-79-5
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: BDIXCFIHERJBEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-1,2,3,4-tetrahydro-5-methoxy-2-oxo-1-(2-propenyl)naphthalene 在 吡啶 、 chromium(VI) oxide 、 氨 、 lithium 作用下， 以 乙醚 、 丙酮 、 苯 为溶剂， 生成
  参考文献：
  名称：

  与二萜生物碱有关的合成中间体。

  摘要：

  DOI：

  10.1021/ja00960a036
• 作为产物：
  描述：

  5-甲氧基-2-萘满酮 、 3-溴丙烯 生成 (+/-)-1,2,3,4-tetrahydro-5-methoxy-2-oxo-1-(2-propenyl)naphthalene
  参考文献：
  名称：

  与二萜生物碱有关的合成中间体。

  摘要：

  DOI：

  10.1021/ja00960a036

文献信息

• Therapeutically useful 2-aminotetralin derivatives
  申请人：The Upjohn Company

  公开号：US06331636B1

  公开（公告）日：2001-12-18

  This invention is therapeutically useful 2-aminotetralins and pharmaceutically acceptable acid addition salts thereof of the formula These compounds are useful to treat central nervous system disorders, hypertension, diabetes, sexual impotency and to control appetite.

  这项发明是治疗有用的2-氨基四氢萘及其药用可接受的酸盐，其化学式为。这些化合物可用于治疗中枢神经系统疾病、高血压、糖尿病、性功能障碍以及控制食欲。
• Centrally acting serotonergic agents. Synthesis and structure-activity relationships of C-1- or C-3-substituted derivatives of 8-hydroxy-2-(di-n-propylamino)tetralin
  作者：Chiu Hong Lin、Susanne R. Haadsma-Svensson、Robert A. Lahti、Robert B. McCall、Montford F. Piercey、Peggy J. K. D. Schreur、Philip F. VonVoigtlander、Connie G. Chidester

  DOI：10.1021/jm00058a003

  日期：1993.3

  The synthesis and structure-activity relationships (SAR) of C-1- or C-3-substituted derivatives of 8-hydroxy-2-(di-n-propylamino)tetralin (8-OH-DPAT) are described. These analogs were synthesized via alkylation of the tetralone derivatives followed by reductive amination. All of the analogs were inactive at the dopamine D2 receptor. Among the 8-OMe or 8-OH C-1,N-disubstituted analogs synthesized, the cis analogs were more potent in the 5-HT1A binding assay than the corresponding trans analogs. However, in the case of 1-(cyclopropylmethyl)-N-n-propyl analogs, the trans isomer has a slightly higher 5-HT1A affinity than its cis counterpart. The order of binding potency for C-1 substitution was found to be allyl > hydroxymethyl> n-propyl > cyclopropylmethyl much greater than carbomethoxy. Interestingly, the 5-OMe analogs were found to be inactive in both the 5-HT1A and dopamine D2 binding assays. In the C-3 allyl-substituted analogs, 5-HT1A agonist activity was found to be considerably lower. In these examples, the trans analogs showed weak 5-HT1A binding activity whereas the cis analogs were inactive. Analogs with C-1,N,N-trisubstitution also showed a marked decrease in 5-HT1A binding affinity. Overall, the SAR study showed that cis C-1 substitution maintains the 5-HT1A agonist activity of 8-OH-DPAT whereas trans C-1 substitution displays somewhat diminished activity. On the other hand, the trans C-3 substitution shows modest agonist activity whereas cis C-3 substitution removes the activity completely.
• THERAPEUTICALLY USEFUL 2-AMINOTETRALIN DERIVATIVES
  申请人：THE UPJOHN COMPANY

  公开号：EP0476016A1

  公开（公告）日：1992-03-25
• US5545755A
  申请人：——

  公开号：US5545755A

  公开（公告）日：1996-08-13
• US6331636B1
  申请人：——

  公开号：US6331636B1

  公开（公告）日：2001-12-18