4-(3,5-Dihydroxyphenyl)-1-phenoxy-butan | 65511-94-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(3,5-Dihydroxyphenyl)-1-phenoxy-butan
• 英文别名: 3-(3,5-dihydroxyphenyl)-1-phenoxybutane；5-(4-phenoxybutan-2-yl)benzene-1,3-diol
• CAS: 65511-94-6
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: BCWZCKDYMFWZLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3,5-Dihydroxyphenyl)-1-phenoxy-butan 生成 dl-5-hydroxy-2,2-dimethyl-7-(1-methyl-3-phenoxypropyl)-4-chromanone
  参考文献：
  名称：

  9-Hydroxydibenzo[b,d]pyrans and intermediates

  摘要：

  9-羟基二苯并[b,d]吡喃可用作镇痛剂、降压药、免疫抑制剂、镇静剂；作为抗分泌和抗焦虑药物；其中间体和具有以下式的衍生物 ##STR1## 其中R为氢或具有一至五个碳原子的烷酰基；R.sub.1为氢、具有一至五个碳原子的烷酰基或--CO--(CH.sub.2).sub.P --NR.sub.2 R.sub.3，其中p为0或1至4的整数；当单独考虑R.sub.2和R.sub.3时，R.sub.2和R.sub.3分别为氢或具有一至四个碳原子的烷基；当R.sub.2和R.sub.3与它们连接的氮一起形成与哌啶基、吡咯基、吡咯啉基、吗啉基和N-烷基哌嗪基中的一种所选的5-或6-成员杂环环；R.sub.4和R.sub.5中的每一个为氢、甲基或乙基；R.sub.0为氧代或具有二至四个碳原子的烷二氧基；Z为(a)具有一至九个碳原子的烷基；(b) --(alk.sub.1).sub.m --X--(alk.sub.2).sub.n --其中每个(alk.sub.1)和(alk.sub.2)具有1至9个碳原子，但要求(alk.sub.1)加(alk.sub.2)中碳原子的总和不大于9；m和n中的每一个为0或1；X为O、S、SO或SO.sub.2；W为甲基、苯基、对氯苯基、对氟苯基、吡啶基、哌啶基、具有3至7个碳原子的环烷基，或单取代环烷基，其中取代基为苯基、对氯苯基或对氟苯基；但要求当W为甲基时，Z为--(alk.sub.1).sub.m --X---(alk.sub.2).sub.n --。

  公开号：

  US04143139A1
• 作为产物：
  描述：

  4-(3,5-Dibenzyloxyphenyl)-1-phenoxy-butan 、 乙醇 、 盐酸 、 氢气 在 钯 silica gel 、 ethyl acetate benzene 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 生成 4-(3,5-Dihydroxyphenyl)-1-phenoxy-butan
  参考文献：
  名称：

  9-Hydroxydibenzo[b,d]pyrans and intermediates therefore

  摘要：

  9-羟基二苯并[b，d]吡喃可用作镇痛剂、降压剂、免疫抑制剂、镇静剂；作为抗分泌和抗焦虑药物；其中间体和衍生物具有以下式子：##STR1## 其中R是氢或具有1至5个碳原子的脂肪酰基；R.sub.1是氢，具有1至5个碳原子的脂肪酰基或--CO--(CH.sub.2).sub.p --NR.sub.2 R.sub.3，其中p为0或1至4的整数；当R.sub.2和R.sub.3分别为氢或具有1至4个碳原子的烷基时；当R.sub.2和R.sub.3与它们连接的氮一起形成选自哌啶基，吡咯基，吡咯烷基，吗啉基和N-烷基哌嗪基的5-或6元杂环环；R.sub.4和R.sub.5中的每一个都是氢，甲基或乙基；R.sub.0为氧代或具有2至4个碳原子的亚烷基二氧基；Z为（a）具有1至9个碳原子的烷基；（b）--(alk.sub.1).sub.m --X--(alk.sub.2).sub.n --其中每个（alk.sub.1）和（alk.sub.2）具有1至9个碳原子，但（alk.sub.1）加上（alk.sub.2）的碳原子总和不大于9；m和n中的每一个都是0或1；X为O，S，SO或SO.sub.2；W为甲基，苯基，对氯苯基，对氟苯基，吡啶基，哌啶基，具有3至7个碳原子的环烷基或单取代环烷基，其中取代基为苯基，对氯苯基或对氟苯基；但当W为甲基时，Z为--(alk.sub.1).sub.m --X--(alk.sub.2).sub.n --。

  公开号：

  US04243674A1

文献信息

• 9-Hydroxyoctahydrobenzo[c]quinolines and their pharmaceutical
  申请人：Pfizer

  公开号：US04380542A1

  公开（公告）日：1983-04-19

  1,9-Dihydroxyoctahydrobenzo[c]quinolines (I), 1-hydroxyhexahydrobenzo[c]quinoline-9(8H)-ones (II), and 1-hydroxy-tetrahydrobenzo[c]quinolines (IV) useful as CNS agents, especially as analgesics and tranquilizers, as hypotensives, as agents for the treatment of glaucoma and as diuretics; intermediates therefor (III) and derivatives thereof.

  1,9-二羟基八氢苯并[c]喹啉(I)，1-羟基六氢苯并[c]喹啉-9(8H)-酮(II)和1-羟基四氢苯并[c]喹啉(IV)可作为中枢神经系统制剂，特别是作为镇痛剂和镇静剂，作为降压剂，作为治疗青光眼的制剂和作为利尿剂；其中间体(III)和其衍生物。
• 9-Hydroxyoctahydrobenzo(c)quinolines analgesic compositions containing
  申请人：Pfizer Inc.

  公开号：US04405626A1

  公开（公告）日：1983-09-20

  1,9-Dihydroxyoctahydrobenzo[c]quinolines (I), 1-hydroxyhexahydrobenzo[c]quinoline-9(8H)-ones (II), and 1-hydroxy-tetrahydrobenzo[c]quinolines (IV) useful as CNS agents, especially as analgesics and tranquilizers, as hypotensives, as agents for the treatment of glaucoma and as diuretics; intermediates therefor (III) and derivatives thereof having the formulae ##STR1## wherein R is hydroxy, alkanoyloxy having from one to five carbon atoms and hydroxymethyl; R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl having from one to five carbon atoms or --CO--(CH.sub.2).sub.p --NR.sub.2 R.sub.3 wherein p is 0 or an integer from 1 to 4; each of R.sub.2 and R.sub.3 when taken individually is hydrogen or alkyl having from one to four carbon atoms; R.sub.2 and R.sub.3 when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring (piperidino, pyrrolo, pyrrolidino, morpholino and N-alkylpiperazino having from one to four carbon atoms in the alkyl group); R.sub.4 is hydrogen, alkyl having from 1 to 6 carbon atoms and --(CH.sub.2).sub.z --C.sub.6 H.sub.5 wherein z is an integer from 1 to 4; R.sub.5 is hydrogen, methyl or ethyl; R.sub.6 is hydrogen, --(CH.sub.2).sub.y -carbalkoxy having from 1 to 4 carbon atoms in the alkoxy group wherein y is 0 or an integer from 1 to 4; carbobenzyloxy, formyl, alkanoyl having from two to five carbon atoms, alkyl having from one to six carbon atoms; --(CH.sub.2).sub.x --C.sub.6 H.sub.5 wherein x is an integer from 1 to 4; and --CO(CH.sub.2).sub.x-1 --C.sub.6 H.sub.5 ; R.sub.0 is oxo, methylene or alkylenedioxy having from two to four carbon atoms; R' is R or R.sub.0 ; Z is (a) alkylene having from one to nine carbon atoms; (b) -(alk.sub.1).sub.m -X-(alk.sub.2).sub.n - wherein each of (alk.sub.1) and (alk.sub.2) is alkylene having from one to nine carbon atoms, with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.2) is not greater than 9; each of m and n is 0 or 1; X is 0, S, SO or SO.sub.2 ; and W is hydrogen, methyl, ##STR2## wherein W.sub.1 is hydrogen, chloro or fluoro; pyridyl, piperidyl, cycloalkyl having from 3 to 7 carbon atoms, or monosubstituted cycloalkyl wherein the substituent is ##STR3## wherein W.sub.2 is hydrogen, chloro or fluoro; and pharmaceutically-acceptable acid addition salts of compounds of formulae I, II and IV and the ketals of compounds of formulae II, III and IV wherein the ketal moiety has from two to four carbon atoms.

  1,9-二羟基八氢苯并[c]喹啉（I），1-羟基六氢苯并[c]喹啉-9（8H）-酮（II）和1-羟基四氢苯并[c]喹啉（IV）可用作中枢神经系统药物，特别是作为镇痛剂和镇静剂，作为降压剂，作为治疗青光眼的药物和作为利尿剂；其中间体（III）和具有以下式子的衍生物##STR1## 其中，R为羟基，有1至5个碳原子的脂肪酰氧基和羟甲基；R.sub.1为氢，苄基，苯甲酰基，有1至5个碳原子的脂肪酰基或--CO--（CH.sub.2）.sub.p--NR.sub.2R.sub.3，其中p为0或1至4的整数；当分别取R.sub.2和R.sub.3时，它们各自为氢或有1至4个碳原子的烷基；当取R.sub.2和R.sub.3时，它们与它们所连接的氮一起形成一个5-或6-成员的杂环环（哌啶，吡咯，吡咯烷，吗啉和N-烷基哌嗪，其中烷基中有1至4个碳原子）；R.sub.4为氢，有1至6个碳原子的烷基和--（CH.sub.2）.sub.z--C.sub.6H.sub.5，其中z为1至4的整数；R.sub.5为氢，甲基或乙基；R.sub.6为氢，--（CH.sub.2）.sub.y-羧基烷氧基，其中烷氧基中有1至4个碳原子，y为0或1至4的整数；羧苄氧基，甲酰基，有2至5个碳原子的脂肪酰基，有1至6个碳原子的烷基；--（CH.sub.2）.sub.x--C.sub.6H.sub.5，其中x为1至4的整数；和--CO（CH.sub.2）.sub.x-1--C.sub.6H.sub.5；R.sub.0为氧代，亚甲基或有2至4个碳原子的烷二氧基；R'为R或R.sub.0；Z为（a）有1至9个碳原子的烷基；（b）-(alk.sub.1).sub.m-X-(alk.sub.2).sub.n-，其中（alk.sub.1）和（alk.sub.2）分别为有1至9个碳原子的烷基，但要求（alk.sub.1）加（alk.sub.2）的碳原子总数不大于9；m和n分别为0或1；X为0，S，SO或SO.sub.2；W为氢，甲基，##STR2## 其中W.sub.1为氢，氯或氟；吡啶基，哌啶基，有3至7个碳原子的环烷基或单取代的环烷基，其中取代基为##STR3## 其中W.sub.2为氢，氯或氟；以及式I，II和IV化合物的药物可接受的酸盐和式II，III和IV化合物的缩醛，其中缩醛基团具有2至4个碳原子。
• 9-Hydroxyoctahydrobenzo[C]quinolines and intermediates therefor
  申请人：Pfizer Inc.

  公开号：US04340737A1

  公开（公告）日：1982-07-20

  1,9-Dihydroxyoctahydrobenzo[c]quinolines (I), 1-hydroxyhexahydrobenzo-[c]quinoline-9(8H)-ones (II), and 1-hydroxy-tetrahydrobenzo[c]quinolines (IV) useful as CNS agents, especially as analgesics and tranquilizers, as hypotensives, as agents for the treatment of glaucoma and as diuretics; intermediates therefor (III) and derivatives thereof having the formulae ##STR1## wherein R is hydroxy, alkanoyloxy having from one to five carbon atoms and hydroxymethyl; R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl having from one to five carbon atoms or --CO--(CH.sub.2).sub.p --NR.sub.2 R.sub.3 wherein p is 0 or an integer from 1 to 4; each of R.sub.2 and R.sub.3 when taken individually is hydrogen or alkyl having from one to four carbon atoms; R.sub.2 and R.sub.3 when taken together with the nitrogen to which they are attached form a 5- to 6-membered heterocyclic ring (piperidino, pyrrolo, pyrrolidino, morpholine and N-alkylpiperazino having from one to four carbon atoms in the alkyl group); R.sub.4 is hydrogen, alkyl having from 1 to 6 carbon atoms and --(CH.sub.2).sub.z --C.sub.6 H.sub.5 wherein z is an integer from 1 to 4; R.sub.5 is hydrogen, methyl or ethyl; R.sub.6 is hydrogen, --(CH.sub.2).sub.y -carbalkoxy having from 1 to 4 carbon atoms in the alkoxy group wherein y is 0 or an integer from 1 to 4; carbobenzyloxy, formyl, alkanoyl having from two to five carbon atoms, alkyl having from one to six carbon atoms; --(CH.sub.2).sub.x --C.sub.6 H.sub.5 wherein x is an integer from 1 to 4; and --CO(CH.sub.2).sub.x-1 --C.sub.6 H.sub.5 ; R.sub.0 is oxo, methylene or alkylenedioxy having from two to four carbon atoms; R' is R or R.sub.0 ; Z is (a) alkylene having from one to nine carbon atoms; (b) --(alk.sub.1).sub.m --X--(alk.sub.2).sub.n --wherein each of (alk.sub.1) and (alk.sub.2) is alkylene having from one to nine carbon atoms, with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.2) is not greater than 9; each of m and n is 0 or 1; X is 0, S, SO or SO.sub.2 ; and W is hydrogen, methyl, ##STR2## wherein W.sub.1 is hydrogen, chloro or fluoro; pyridyl, piperidyl, cycloalkyl having from 3 to 7 carbon atoms, or monosubstituted cycloalkyl wherein the substituent is ##STR3## wherein W.sub.2 is hydrogen, chloro or fluoro; and pharmaceutically-acceptable acid addition salts of compounds of formulae I, II and IV and the ketals of compounds of formulae II, III and IV wherein the ketal moiety has from two to four carbon atoms.

  1,9-二羟基八氢苯并[c]喹啉(I)，1-羟基六氢苯并[c]喹啉-9(8H)-酮(II)，以及1-羟基四氢苯并[c]喹啉(IV)可用作中枢神经系统制剂，特别是作为镇痛剂和镇静剂，作为降压剂，作为治疗青光眼的制剂以及作为利尿剂；其中间体(III)和其衍生物具有以下式子：##STR1## 其中R为羟基，从一到五个碳原子的烷酰氧基和羟甲基；R.sub.1为氢，苯甲基，苯甲酰基，从一到五个碳原子的烷酰基或--CO--(CH.sub.2).sub.p --NR.sub.2 R.sub.3，其中p为0或1到4的整数；当R.sub.2和R.sub.3分别为氢或含有从一到四个碳原子的烷基时；当R.sub.2和R.sub.3与它们连接的氮一起形成一个5-到6-成员的杂环环(哌啶，吡咯，吡咯烷，吗啉和N-烷基哌嗪，烷基中的碳原子数从一到四)；R.sub.4为氢，含有1到6个碳原子的烷基和--(CH.sub.2).sub.z --C.sub.6 H.sub.5，其中z为1到4的整数；R.sub.5为氢，甲基或乙基；R.sub.6为氢，--(CH.sub.2).sub.y-碳基氧酰基，其中烷氧基中的碳原子数为1到4，y为0或1到4的整数；羧苄氧基，甲酰基，从二到五个碳原子的烷酰基，含有从一到六个碳原子的烷基；--(CH.sub.2).sub.x --C.sub.6 H.sub.5，其中x为1到4的整数；和--CO(CH.sub.2).sub.x-1 --C.sub.6 H.sub.5；R.sub.0为氧代，亚甲基或含有从二到四个碳原子的亚烷基二氧基；R'为R或R.sub.0；Z为(a)含有从一到九个碳原子的烷基；(b)--(alk.sub.1).sub.m --X--(alk.sub.2).sub.n --其中(alk.sub.1)和(alk.sub.2)都是含有从一到九个碳原子的烷基，但是(alk.sub.1)加上(alk.sub.2)的碳原子总和不大于9；m和n都为0或1；X为0，S，SO或SO.sub.2；W为氢，甲基，##STR2## 其中W.sub.1为氢，氯或氟；吡啶基，哌啶基，含有从3到7个碳原子的环烷基或单取代的环烷基，其中取代基为##STR3## 其中W.sub.2为氢，氯或氟；以及具有式I、II和IV的化合物的药学上可接受的酸加成盐和具有式II、III和IV的酮的缩醛，其中缩醛基团具有从二到四个碳原子。
• US4143139A
  申请人：——

  公开号：US4143139A

  公开（公告）日：1979-03-06
• US4243674A
  申请人：——

  公开号：US4243674A

  公开（公告）日：1981-01-06