trans-1-pyrrolidinyl-2-hydroxy-1,2,3,4-tetrahydronaphthalene | 32635-41-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: trans-1-pyrrolidinyl-2-hydroxy-1,2,3,4-tetrahydronaphthalene
• 英文别名: trans-1,2,3,4-Tetrahydro-2-hydroxy-1-(pyrrolidin-1-yl)naphthalene；(1R,2R)-1-pyrrolidin-1-yl-1,2,3,4-tetrahydronaphthalen-2-ol
• CAS: 32635-41-9；125444-98-6
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: RGEQLCZKYGQAFO-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-1-pyrrolidinyl-2-hydroxy-1,2,3,4-tetrahydronaphthalene 在 甲基磺酰氯 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 37.5h， 生成 trans-2-pyrrolidinyl-1-(N-methyl-3',4'-dichlorobenzamido)-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Naphtho and benzo analogs of the .kappa. opioid agonist trans-(.+-.)-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]benzeneacetamide

  摘要：

  Further elaboration on the structure-activity relationships in our U-50,488 series has revealed that benzologation of this cyclohexane-1,2-diamine derivative provides compounds which either maintain the interaction with the kappa-receptor (e.g. compounds 3a and 5a in the phenylacetamido series) or eliminate the mu-receptor mediated analgesia (e.g. compounds 3-6 in the benzamido series). Naphthologation also caused the elimination of mu-receptor mediated analgesia (e.g. compounds 17a and 17b).

  DOI：

  10.1021/jm00110a021
• 作为产物：
  描述：

  1,2-二氢萘 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 16.58h， 生成 trans-1-pyrrolidinyl-2-hydroxy-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Naphtho and benzo analogs of the .kappa. opioid agonist trans-(.+-.)-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]benzeneacetamide

  摘要：

  Further elaboration on the structure-activity relationships in our U-50,488 series has revealed that benzologation of this cyclohexane-1,2-diamine derivative provides compounds which either maintain the interaction with the kappa-receptor (e.g. compounds 3a and 5a in the phenylacetamido series) or eliminate the mu-receptor mediated analgesia (e.g. compounds 3-6 in the benzamido series). Naphthologation also caused the elimination of mu-receptor mediated analgesia (e.g. compounds 17a and 17b).

  DOI：

  10.1021/jm00110a021

文献信息

• Benzo-fused cycloalkane and oxa- and thia-, cycloalkane
  申请人：E. I. Du Pont De Nemours and Company

  公开号：US04929627A1

  公开（公告）日：1990-05-29

  Benzo-fused cycloalkane and oxa- and thia-cycloalkane trans-1,2-diamine compounds of the formula: ##STR1## wherein A, B, C, D, n, X, Y, R, R.sup.1, R.sup.2 and R.sup.3 are as defined in the specification, e.g., trans-3,4-dichloro-N-methyl-N-[2-(pyrrolidin-1-yl)-5-methoxy-1,2,3,4-tetra hydronaphth-1-yl]benezeneacetamide, and the pharmaceutically acceptable salts or N-oxides thereof, are useful as analgesics and/or diuretics.

  苯并环烷和氧杂环烷、硫杂环烷的反-1,2-二胺化合物的化学式如下：##STR1## 其中A、B、C、D、n、X、Y、R、R.sup.1、R.sup.2和R.sup.3的定义如说明书中所述，例如trans-3,4-二氯-N-甲基-N-[2-(吡咯烷-1-基)-5-甲氧基-1,2,3,4-四氢萘-1-基]苯乙酰胺，以及其药学上可接受的盐或N-氧化物，可用作镇痛剂和/或利尿剂。
• Benzo-fused cycloalkane and oxa- and thia-cycloalkane trans-1,2-diamine
  申请人：E. I. du Pont de Nemours and Company

  公开号：US05010085A1

  公开（公告）日：1991-04-23

  Benzo-fused cycloalkane and oxa- and thia-cycloalkane trans-1,2-diamine compounds of the formula: ##STR1## wherein A, B, C, D, n, X, Y, R, R.sup.1, R.sup.2 and R.sup.3 are as defined in the specification, e.g., trans-3,4-dichloro-N-methyl-[2-(pyrrolidin-1-yl)-5-methoxy-1,2,3,4-tetrahy dronaphth-1-yl]benzeneacetamide, and the pharmaceutically acceptable salts or N-oxides thereof, are useful as analgesics and/or diuretics.

  苯并环烷和氧杂环烷、硫杂环烷的trans-1,2-二胺化合物的化学式为：##STR1## 其中A、B、C、D、n、X、Y、R、R.sup.1、R.sup.2和R.sup.3如说明书中所定义，例如trans-3,4-二氯-N-甲基-[2-(吡咯烷-1-基)-5-甲氧基-1,2,3,4-四氢萘-1-基]苯乙酰胺以及其药学上可接受的盐或N-氧化物，可用作镇痛剂和/或利尿剂。
• Benzocyclohexanes and analgesic compositions thereof
  申请人：Roussel Uclaf

  公开号：US05068244A1

  公开（公告）日：1991-11-26

  Novel all possible enantiomeric and diastereoisomeric forms of compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, halogen, alkyl and alkoxy of 1 to 5 carbon atoms, --NO.sub.2, --NH.sub.2 and mono and dialkylamino of 1 to 5 alkyl carbon atoms, n is 1 or 2, A and B have the trans configuration, one of A and B being ##STR2## R.sub.2 is hydrogen or alkyl of 1 to 5 carbon atoms, Z is --(CH.sub.2)--.sub.n2, n.sub.2 being an integer from 0 to 5 or branched alkylene of 2 to 8 carbon atoms or --CH.sub.2 --O--, Y is selected from the group consisting of phenyl, naphthyl, indenyl, heteromonocycle of 5 to 6 ring atoms and heterobicycle, all optionally having at least one substituent and the other of A and B is ##STR3## R.sub.4 and R.sub.5 individually being selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms or taken together with the nitrogen to which they are attached form a 5 to 6 ring heterocycle optionally containing a heteroatom selected from the group consisting of --O--, --S-- and --NH-- with the proviso 1) A is ##STR4## wherein R.sub.4 l and R.sub.5 have the above definitions and B is ##STR5## wherein R.sub.2, Z and Y have the above definition or 2) Z is --(CH.sub.2).sub.n2 -- and n.sub.2 is 0,2,3,4 or 5 or branched alkylene of 2 to 8 carbon atoms or --CH.sub.2 O-- yr 3) Y is phenyl substituted with at least one member of the group consisting of alkyl of 1 to 5 carbon atoms, alkoxy of 2 to 5 carbon atoms, --NH.sub.2 and mono and dialkylamino or 4) Y is naphthyl, indenyl, heteromonocycle of 5 to 6 ring atoms or heterobicycle, all optionally substituted with at least one substituent, except unsubstituted benzothiophene or 5) R.sub.1 is --NO.sub.2 or 6) R.sub.2 is alkyl of 4 to 5 carbon atoms or 7) R.sub.1 is hydrogen, n.sub.1 is 1, A is ##STR6## Y is selected from the group consisting of 3,4-dimethoxy-phenyl, 4-nitro-phenyl and benzothienyl and B is pyrrolidinyl or 8) R.sub.1 is hydrogen, n.sub.1 is 2, A is ##STR7## Y is selected from the group consisting of 3,4-dimethoxy-phenyl, 3,4-dichloro-phenyl, 4-trifluoromethyl-phenyl, 4-nitro-phenyl and benzothienyl and B is pyrrolidinyl and their non-toxic, pharmaceutically acceptable acid addition salts having central analgesic properties and a strong affinity for opiate receptors.

  该专利涵盖了化合物的所有可能的对映异构体和顺反异构体，其化学式为##STR1##其中R.sub.1选自氢、卤素、1至5个碳原子的烷基和烷氧基、--NO.sub.2、--NH.sub.2和1至5个碳原子的单烷基和双烷基氨基，n为1或2，A和B具有反式构型，其中一个为##STR2##R.sub.2为氢或1至5个碳原子的烷基，Z为--(CH.sub.2)--.sub.n2，n.sub.2为0至5的整数或2至8个碳原子的支链烷基或--CH.sub.2--O--，Y选自苯基、萘基、茚基、5至6个环原子的杂环和杂环，所有这些都可以选择至少一个取代基，另一个为##STR3##R.sub.4和R.sub.5分别选自氢和1至5个碳原子的烷基，或与它们连接的氮一起形成一个5至6个环的杂环，其中杂原子选自--O--、--S--和--NH--，但前提是：1）A为##STR4##其中R.sub.4和R.sub.5具有上述定义，B为##STR5##其中R.sub.2、Z和Y具有上述定义，或2）Z为--(CH.sub.2).sub.n2--，n.sub.2为0、2、3、4或5，或2至8个碳原子的支链烷基或--CH.sub.2 O--，或3）Y为至少与1个选自1至5个碳原子的烷基、2至5个碳原子的烷氧基、--NH.sub.2和单烷基和双烷基氨基的群体成员取代的苯基，或4）Y为萘基、茚基、5至6个环原子的杂环或杂环，所有这些都可以选择至少一个取代基，但不包括未取代的苯并噻吩，或5）R.sub.1为--NO.sub.2，或6）R.sub.2为4至5个碳原子的烷基，或7）R.sub.1为氢，n.sub.1为1，A为##STR6##Y选自3,4-二甲氧基苯基、4-硝基苯基和苯并噻吩，B为吡咯烷基，或8）R.sub.1为氢，n.sub.1为2，A为##STR7##Y选自3,4-二甲氧基苯基、3,4-二氯苯基、4-三氟甲基苯基、4-硝基苯基和苯并噻吩，B为吡咯烷基。这些化合物的非毒性、药学上可接受的酸盐具有中枢镇痛特性和对阿片受体的强亲和力。
• Benoz-fused cycloalkane trans-1,2-diamine derivatives
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04876269A1

  公开（公告）日：1989-10-24

  Benzo-fused cycloalkane and oxa- and thia-cycloalkane trans-1,2-diamine compounds of the formula: ##STR1## wherein A, B, C, D, n, X, Y, R, R.sup.1, R.sup.2 and R.sup.3 are as defined in the specification, e.g., trans-3,4-dichloro-N-methyl-N-[2-(pyrrolidin-1-yl)-5-methoxy-1,2,3,4-tetra hydronaphth-1-yl]benzeneacetamide, and the pharmaceutically acceptable salts of N-oxides thereof, are useful as analgesics and/or diuretics.

  苯并环烷和氧杂环烷、硫杂环烷的trans-1,2-二胺化合物的化学式为：##STR1## 其中A、B、C、D、n、X、Y、R、R.sup.1、R.sup.2和R.sup.3的定义如规范中所述，例如trans-3,4-二氯-N-甲基-N-[2-(吡咯烷-1-基)-5-甲氧基-1,2,3,4-四氢萘-1-基]苯乙酰胺，以及其N-氧化物的药学上可接受的盐，可用作镇痛剂和/或利尿剂。
• CLEMENCE, FRANCOIS;FORTIN, MICHEL;FRECHET, DANIEL;MOURA, ANNE-MARIE
  作者：CLEMENCE, FRANCOIS、FORTIN, MICHEL、FRECHET, DANIEL、MOURA, ANNE-MARIE

  DOI：——

  日期：——