N-n-Propyl-3-(3-hydroxyphenyl)piperidine hydrochloride | 79054-96-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-n-Propyl-3-(3-hydroxyphenyl)piperidine hydrochloride
• 英文别名: (+/-)-3-PPP hydrochloride；(+/-)-3-(3-hydroxyphenyl)-N-propylpiperidine hydrochloride；Phenol, 3-(1-propyl-3-piperidinyl)-, hydrochloride；3-(1-propylpiperidin-3-yl)phenol;hydrochloride
• CAS: 79054-96-9
• 化学式: C₁₄H₂₁NO*ClH
• 分子量: 255.788
• InChiKey: NRHUDETYKUBQJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  23.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  氯磷酸二乙酯 、 N-n-Propyl-3-(3-hydroxyphenyl)piperidine hydrochloride 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以81%的产率得到3-<3-(diethylphosphono)phenyl>-N-propylpiperidine
  参考文献：
  名称：

  Carbamate ester derivatives as potential prodrugs of the presynaptic dopamine autoreceptor agonist (-)-3-(3-hydroxyphenyl)-N-propylpiperidine

  摘要：

  Twenty derivatives bearing substituents on the phenolic function of (-)-3-(3-hydroxyphenyl)-N-propylpiperidine [(-)-3-PPP] were synthesized and tested as prodrugs. The carbamate ester derivatives were found to be the most suitable prodrugs, and especially the 4-isopropylphenylcarbamate 20 was capable of escaping the first-pass metabolism and still generating high plasma levels of the parent compound. Four hours after an oral dose of 100 mumol/kg to rats, a plasma level of 2400 nmol/L of (-)-3-PPP was detected by an HPLC method. This was 90 times the level reached after 4 h (27 nmol/L) when (-)-3-PPP itself was given orally at the same dose.

  DOI：

  10.1021/jm00394a014
• 作为产物：
  描述：

  3-(3-aminophenyl)-N-n-propylpiperidine 在 sodium nitrite 作用下， 以 硫酸 、 水 为溶剂， 以0.059 g (20%)的产率得到N-n-Propyl-3-(3-hydroxyphenyl)piperidine hydrochloride
  参考文献：
  名称：

  Substituted phenyl piperidines

  摘要：

  该公式化合物为##STR1##，其中n为1或2，Y为OH，R.sup.1 COO--，R.sup.2 R.sup.3 NCOO--或R.sup.4 O，其中R.sup.1为烷基或可能取代的苯基，R.sup.2为烷基、苯乙基、苄基或苯基，R.sup.3为H或烷基，R.sup.4为烯丙基或苄基，R为烷基、羟基烷基、二甲基氨基烷基或甲硫基烷基或烯基，其制备方法以及利用这些化合物的药物制剂和治疗方法。这些化合物可用于治疗目的，尤其用于治疗中枢神经系统疾病。

  公开号：

  US04426386A1

文献信息

• Phenyl-azacykloalkanes
  申请人：Carlsson; Per Arvid Emil

  公开号：US04937346A1

  公开（公告）日：1990-06-26

  Compound of the formula ##STR1## wherein n is 1 or 2, Y is OH, R.sup.1 COO--, R.sup.2 R.sup.3 NCOO-- or R.sup.4 O whereby R.sup.1 is an alkyl group, or a possibly substituted phenyl group, R.sup.2 is an alkyl, phenethyl, or benzyl or phenyl group, R.sup.3 is H or an alkyl group and R.sup.4 is an allyl or benzyl group, and R is an alkyl, hydroxyalkyl, dimethylaminoalkyl or methylthioalkyl group or alkenyl group, processes for their preparations and methods of treatment employing such compounds. The compounds are useful for therapeutic purposes, especially for treatment of disorders in the central nervous system.

  化合物的公式为##STR1##其中n为1或2，Y为OH，R.sup.1 COO--，R.sup.2 R.sup.3 NCOO--或R.sup.4 O，其中R.sup.1是烷基或可能被取代的苯基，R.sup.2是烷基、苯乙基、苄基或苯基，R.sup.3是H或烷基，R.sup.4是烯丙基或苄基，R是烷基、羟基烷基、二甲氨基烷基或甲硫基烷基或烯基，其制备方法和应用这些化合物的治疗方法。这些化合物在治疗用途中非常有用，尤其是用于治疗中枢神经系统疾病。
• Phenyl-azacycloalkanes and use thereof in treatment of central nervous
  申请人：Carlsson; Per A. E.

  公开号：US04719219A1

  公开（公告）日：1988-01-12

  Compound of the formula ##STR1## wherein n is 1 or 2, Y is OH, R.sup.1 COO--, R.sup.2 R.sup.3 NCOO-- or R.sup.4 O whereby R.sup.1 is an alkyl group, or a possibly substituted phenyl group, R.sup.2 is an alkyl, phenethyl, or benzyl or phenyl group, R.sup.3 is H or an alkyl group and R.sup.4 is an allyl or benzyl group, and R is an alkyl, hydroxyalkyl, dimethylaminoalkyl or methylthioalkyl group or alkenyl group, processes for their preparations and methods of treatment employing such compounds. The compounds are useful for therapeutic purposes, especially for treatment of disorders in the central nervous system.

  该化合物的结构为##STR1##，其中n为1或2，Y为OH，R.sup.1 COO--，R.sup.2 R.sup.3 NCOO--或R.sup.4 O，其中R.sup.1为烷基或可能取代的苯基，R.sup.2为烷基、苯乙基、苄基或苯基，R.sup.3为H或烷基，R.sup.4为烯丙基或苄基，R为烷基、羟基烷基、二甲胺基烷基、甲硫基烷基或烯基，其制备方法和治疗方法。这些化合物可用于治疗目的，尤其是用于治疗中枢神经系统疾病。
• New phenyl-azacycloalkanes, processes for preparation and pharmaceutical preparations for such compounds
  申请人：Astra Läkemedel Aktiebolag

  公开号：EP0030526A1

  公开（公告）日：1981-06-17

  Compounds of the formula wherein n is 1 or 2, Y is OH, R'COO-, R2R3NCOO- or R4O whereby R1 is an alkyl group, or a possibly substituted phenyl group, R2 is an alkyl, phenethyl, benzyl or phenyl group, R3 is H or an alkyl group and R4 is an allyl or benzyl group, and R is an alkyl, hydroxyalkyl, dimethylaminoalkyl or methylthioalkyl group or alkenyl group, processes for their preparation and pharmaceutical preparations and methods of treatment employing such compounds. The compounds are useful for therapeutic purposes, especially for treatment of disorders in the central nervous system.

  式中化合物 其中 n 是 1 或 2，Y 是 OH、R'COO-、R2R3NCOO- 或 R4O 其中 R1 是烷基或可能取代的苯基，R2 是烷基、苯乙基、苄基或苯基，R3 是 H 或烷基，R4 是烯丙基或苄基，R 是烷基、羟基烷基、二甲基氨基烷基或甲硫基烷基或烯基，其制备工艺和药物制剂以及使用此类化合物的治疗方法。这些化合物可用于治疗目的，特别是治疗中枢神经系统疾病。
• New compounds useful as intermediates or starting materials for preparation of therapeutically useful phenyl-azacycloalkanes
  申请人：Carlsson, Per Arvid Emil

  公开号：EP0084920A2

  公开（公告）日：1983-08-03

  Compounds of the formula wherein Z3 is R or R6CO, wherein R is an alkyl group having 1-5 carbon atoms, a hydroxyalkyl, dimethylaminoalkyl or methylthioalkyl group having 2-6 carbon atoms in the alkyl part and having the heteroatom bound in a position other than 1-position, an alkenyl group having 3-5 carbon atoms other than an 1- alkenyl group, and R6 is an alkyl or alkoxy group containing 1-4 carbon atoms or an alkenyl group with 2-4 carbon atoms, R is an alkyl group with 1-5 carbon atoms, an allyl or benzyl group, and n is 1 or 2 provided that Z3 is other than methyl and ethyl when n is 2 and R7 is CH3 or an acid addition salt thereof. The compounds are useful as intermediates or starting materials for preparation of therapeutically useful substituted phenyl-azacycloalkanes.

  式中的化合物 其中 Z3 是 R 或 R6CO，其中 R 是含有 1-5 个碳原子的烷基、烷基部分含有 2-6 个碳原子且杂原子结合在 1 位以外位置的羟基烷基、二甲基氨基烷基或甲基硫代烷基、含有 3-5 个碳原子的烯基（1-烯基除外）、R6 是含有 1-4 个碳原子的烷基或烷氧基，或含有 2-4 个碳原子的烯基，R 是含有 1-5 个碳原子的烷基、烯丙基或苄基，n 是 1 或 2，条件是当 n 为 2 时，Z3 不是甲基和乙基，R7 是 CH3 或其酸加成盐。这些化合物可作为中间体或起始原料，用于制备对治疗有用的取代苯基氮杂环烷烃。
• Piperidine derivatives, processes for their preparation and pharmaceutical preparation containing them
  申请人：Carlsson, Per Arvid Emil

  公开号：EP0097628A2

  公开（公告）日：1984-01-04

  The pure enantiomeric form of a compound of the formula wherein Y is OH, R'COO, R2R3NCOO- or R4O whereby R' is an aliphatic hydrocarbon residue having 1-17 carbon atoms. a phenyl, 2,6-dimethylphenyl or 3- or 4-hydroxyphenyl group or a 3- or 4-alkanoyloxyphenyl group with the formula wherein R5 is an alkyl group having 1-6 cabon atoms, or RI is a group wherein R6 is hydrogen, an alkyl group having 1 to 5 carbon atoms or a phenyl group, R7 is hydrogen, an alkyl group having 1 to 5 carbon atoms or an acyl group and R8 is hydrogen or an alkyl group having 1 to 5 carbon atoms, R2 is hydrogen, an alkyl group having 1-5 carbon atoms, a phenethyl, benzyl or phenyl group which may be mono- or disubstituted in the aromatic part with a methyl, methoxy, hydroxy, nitro or cyano group or a halogen, R3 is H, an alkyl group having 1 to 5 carbon atoms or a phenyl group or R2 and R3 together with the nitrogen atom form a 5, 6 or 7 membered ring that may contain 1 to 3 double bonds andior 1 or 2 further heteroatoms selected from N, 0 and S, and R4 is an allyl or benzyl group, said enantiomer having the same absolute configuration at the asymmetric carbon atom (x) as that of the (-)-enantiomer of the compound of formula wherein Y is OH, as bases and pharmaceutically acceptable acid addition salts thereof, processes for their preparation and pharmaceutical preparations and methods of treatment employing such compounds. The compounds are useful for treatment of disorders in the central nervous system.

  式中化合物的纯对映体形式 式中 Y 为 OH、R'COO、R2R3NCOO- 或 R4O，其中 R'为具有 1-17 个碳原子的脂肪族烃残基。 式中苯基、2,6-二甲基苯基或 3-或 4-羟基苯基或 3-或 4-烷酰氧基苯基。 其中 R5 是具有 1-6 个碳原子的烷基，或 RI 是一个基团 其中 R6 是氢、1-5 个碳原子的烷基或苯基，R7 是氢、1-5 个碳原子的烷基或酰基，R8 是氢或 1-5 个碳原子的烷基，R2 是氢、1-5 个碳原子的烷基、苯乙基、苄基或苯基，其芳香部分可与甲基、甲氧基、羟基、硝基或氰基或卤素单取代或二取代，R3 是 H、1-5 个碳原子的烷基或苯基，或 R2 和 R3 与氮原子一起形成 5、R4是烯丙基或苄基，所述对映体在不对称碳原子（x）上的绝对构型与式化合物的（-）-对映体的绝对构型相同，其中Y是OH，作为其碱和药学上可接受的酸加成盐、其制备工艺和药物制剂以及采用此类化合物的治疗方法。这些化合物可用于治疗中枢神经系统疾病。