3-phenoxypropyl methanesulfonate | 119967-33-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-phenoxypropyl methanesulfonate
• 英文别名: 3-phenoxy-1-propanol methanesulphonate；methanesulfonic acid 3-phenoxypropyl ester
• CAS: 119967-33-8
• 化学式: C₁₀H₁₄O₄S
• 分子量: 230.285
• InChiKey: RPRHPCTXZAZXGB-UHFFFAOYSA-N

物化性质

• 沸点：
  406.9±28.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-phenoxypropyl methanesulfonate 在 gold(III) chloride 、 silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 48.0h， 以45%的产率得到3,4-二氢-1H-苯并吡喃
  参考文献：
  名称：

  Direct Functionalization of Arenes by Primary Alcohol Sulfonate Esters Catalyzed by Gold(III)

  摘要：

  Alkylation of arenes by primary alcohol triflate or methanesulfonate esters can be efficiently catalyzed by AuCl3 with silver triflate.

  DOI：

  10.1021/ja046890q
• 作为产物：
  描述：

  烯丙基苯基醚 在 dimethyl sulfide borane 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 生成 3-phenoxypropyl methanesulfonate
  参考文献：
  名称：

  Discovery of LASSBio-772, a 1,3-benzodioxole N-phenylpiperazine derivative with potent alpha 1A/D-Adrenergic receptor blocking properties

  摘要：

  We described herein the discovery of 1-(2-(benzo[d] [1,3]dioxol-6-yl)ethyl)-4-(2-methoxyphenyl) piperazine (LASSBio-772), as a novel potent and selective alpha 1A/1D adrenoceptor (AR) antagonist selected after screening of functionalized N-phenylpiperazine derivatives in phenylephrine-induced vasoconstriction of rabbit aorta rings. The affinity of LASSBio-772 for alpha 1A and alpha 1B AR subtypes was determined through displacement of [(3)H]prazosin binding. We obtained Ki values of 0.14 nM for the alpha 1A-AR, similar to that displayed by tamsulosin (K(i) = 0.13 nM) and 5.55 nM for the alpha 1B-AR, representing a 40-fold higher affinity for alpha 1A-AR. LASSBio-772 also presented high affinity (K(B) = 0.025 nM) for the alpha 1D-AR subtype in the functional rat aorta assay, showing to be equipotent to tamsulosin (K(B) = 0.017 nM). (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.032

文献信息

• New antihistaminic N-heterocyclic 4-piperidinamines. 3. Synthesis and antihistaminic activity of N-(4-piperidinyl)-3H-imidazo[4,5-b]pyridin-2-amines
  作者：Frans Janssens、Joseph Torremans、Marcel Janssen、Raymond A. Stokbroekx、Marcel Luyckx、Paul A. J. Janssen

  DOI：10.1021/jm00150a030

  日期：1985.12

  the bioisosteric replacement of a 2-pyridyl ring for a phenyl nucleus in astemizole, a series of N-(4-piperidinyl)-3H-imidazo[4,5-b]pyridin-2-amines was synthesized and evaluated. The title compounds were obtained starting from either 8a or 8b by four synthetic methods. The in vivo antihistamine activity was evaluated by the compound 48/80-induced lethality test in rats and the histamine-induced lethality

  为了研究阿司咪唑中苯基核的2-吡啶基环的生物立体取代，合成并评估了一系列N-（4-哌啶基）-3H-咪唑并[4,5-b]吡啶-2-胺。通过四种合成方法从8a或8b开始获得标题化合物。口服和/或皮下给药后，通过化合物48/80在大鼠中的致死性测试和豚鼠中组胺在致死性中的测试来评估体内抗组胺活性。化合物37（阿司咪唑的等排物）在大鼠中显示出最有效的抗组胺特性。但是，就作用持续时间和总效力而言，阿司咪唑优于37。
• Chemical compounds
  申请人：Glaxo Group Limited

  公开号：US04937268A1

  公开（公告）日：1990-06-26

  This invention relates to compounds of the general formula (I) and physiologically acceptable salts and solvates thereof wherein Ar represents ##STR1## where R.sup.3 is a bond or a straight or branched C.sub.1-2 alkylene group, R.sup.4 is a hydroxy group or a group R.sup.5 NH-- where R.sup.5 represents a group CH.sub.3 SO.sub.2 --, HCO-- or NH.sub.2 CO--, ##STR2## where R.sup.6 is a chlorine atom or the group F.sub.3 C--, ##STR3## k represents an integer from 1 to 8, m represents zero or an integer from 2 to 7 and n represents an integer from 2 to 7 with the proviso that the sum total of k, m and n is 4 to 12; R.sup.1 and R.sup.2 each represents a hydrogen atom or a methyl or ethyl group with the proviso that the sum total of carbon atoms in R.sup.1 and R.sup.2 is not more than 2; R.sup.30 represents hydrogen or C.sub.1-2 alkyl; X represents an oxygen or sulphur atom; and Y and Q may each represent a bond or an oxygen or sulphur atom with the provisos that at least one of Y and Q represents an oxygen or sulphur atom and when Y is a bond m is zero, or when Y represents an oxygen or sulphur atom m is an integer from 2 to 7; P represents a phenyl group optionally substituted by one or more substituents selected from halogen atoms, or the groups C.sub.1-3 alkyl, C.sub.1-3 alkoxy, hydroxy, --CH.sub.2 OH--, --(CH.sub.2).sub.2 OH, --CO.sub.2 H, --CO.sub.2 CH.sub.3, --CO.sub.2 (CH.sub.2).sub.2 CH.sub.3, --R.sup.7, COR.sup.7, --NHCOR.sup.8 and --NR.sup.9 SO.sub.2 R.sup.10 ; where R.sup.7 represents an amino, aminoC.sub.1-3 alkyl, aminoC.sub.1-3 dialkyl, pyrrolidino, piperidino, hexamethyleneimino, piperazino, N-methylpiperazino or morpholino group; R.sup.8 represents a hydrogen atom or a C.sub.1-4 alkyl, C.sub.1-4 alkoxy, phenyl or amino group; R.sup.9 represents a hydrogen atom or a methyl group; R.sup.10 represents a methyl, phenyl, amino or dimethylamino group; or P represents a pyridyl group optionally substituted by one or two substitutents selected from halogen atoms or hydroxy, C.sub.1-3 alkyl and C.sub.1-3 alkoxy groups. The compounds have a stimulant action at .beta..sub.2 -adrenoreceptors and are useful, in particular, in the treatment of diseases associated with reversible airways obstruction such as asthma and chronic bronchitis.

  本发明涉及一般式（I）的化合物及其生理上可接受的盐和溶剂化物，其中Ar代表##STR1##其中R.sup.3是键或直链或支链C.sub.1-2烷基，R.sup.4是羟基或R.sup.5 NH--基团，其中R.sup.5代表CH.sub.3 SO.sub.2 --，HCO--或NH.sub.2 CO--，##STR2##其中R.sup.6是氯原子或F.sub.3 C--基团，##STR3##k表示1至8的整数，m表示零或2至7的整数，n表示2至7的整数，但k、m和n的总和为4至12；R.sup.1和R.sup.2分别表示氢原子或甲基或乙基基团，但R.sup.1和R.sup.2中的碳原子总数不超过2；R.sup.30代表氢或C.sub.1-2烷基；X代表氧或硫原子；Y和Q可以分别表示键或氧或硫原子，但至少有一个Y和Q表示氧或硫原子，当Y是键时，m为零，或当Y表示氧或硫原子时，m为2至7的整数；P表示苯基，可选地取代一个或多个从卤原子中选择的取代基，或羟基，--CH.sub.2 OH--，--（CH.sub.2）.sub.2 OH，--CO.sub.2 H，--CO.sub.2 CH.sub.3，--CO.sub.2（CH.sub.2）.sub.2 CH.sub.3，--R.sup.7，COR.sup.7，--NHCOR.sup.8和--NR.sup.9 SO.sub.2 R.sup.10；其中R.sup.7表示氨基，氨基C.sub.1-3烷基，氨基C.sub.1-3二烷基，吡咯烷基，哌啶基，己亚甲基亚胺基，哌嗪基，N-甲基哌嗪基或吗啉基团；R.sup.8表示氢原子或C.sub.1-4烷基，C.sub.1-4烷氧基，苯基或氨基团；R.sup.9表示氢原子或甲基基团；R.sup.10表示甲基，苯基，氨基或二甲基氨基基团；或P表示吡啶基，可选地取代一个或两个从卤原子或羟基，C.sub.1-3烷基和C.sub.1-3烷氧基中选择的取代基。这些化合物在β.sub.2-肾上腺素受体上具有刺激作用，特别适用于治疗可逆性气道阻塞相关疾病，如哮喘和慢性支气管炎。
• Methods of treating alzheimer's disease
  申请人：Nieman A. James

  公开号：US20060079533A1

  公开（公告）日：2006-04-13

  Disclosed are methods for treating Alzheimer's disease, and other diseases, and/or inhibiting beta-secretase enzyme, and/or inhibiting deposition of A beta peptide in a mammal, by use of 3,4-disubstituted piperidinyl compounds of formula (I) wherein the variables R 1 , R 2 , R 3 , R 4 , Q, W, X, Z, m, and n are defined herein.

  本发明公开了一种治疗阿尔茨海默病和其他疾病、抑制β-分泌酶酶和/或抑制哺乳动物中A beta肽沉积的方法，使用式(I)的3,4-二取代哌啶基化合物，其中变量R1、R2、R3、R4、Q、W、X、Z、m和n在此定义。
• Ethanolamine derivates, processes for their preparation and pharmaceutical compositions containing them
  申请人：GLAXO GROUP LIMITED

  公开号：EP0286242A2

  公开（公告）日：1988-10-12

  This invention relates to compounds of the general formula (I) and physiologically acceptable salts and solvates thereof where Ar represents where R3 is a bond or a straight or branched C1 2alkylene group, R4 is a hydroxy group or a group R5NH-where R5 represents a group CH3SO2-, HCO-or NH2CO-, where R6 is a chlorine atom or the group F3C-, k represents an integer from 1 to 8, m represents zero or an integer from 2 to 7 and n represents an integer from 2 to 7 with the proviso that the sum total of k. m and n is 4 to 12; R1 and R2 each represents a hydrogen atom or a methyl or ethyl group with the proviso that the sum total of carbon atoms in R1 and R2 is not more than 2; R30 represents hydrogen or C12alkyl; X represents an oxygen or sulphur atom: and Y and Q may each represent a bond or an oxygen or sulphur atom with the provisos that at least one of Y and Q represents an oxygen or sulphur atom and when Y is a bond m is zero, or when Y represents an oxygen or sulphur atom m is an integer from 2 to 7: P represents a phenyl group otionally substituted by one or more substituents selected from halogen atoms, or the groups C1 3alkyl, C1 3alkoxy, hydroxy, -CH2OH-, -(CH2)2OH, -CO2H. -CO2CH3, ·CO2(CH2)-2CH3, -R7, COR7, -NHCORs and ·NR9SO2R10; where R7 represents an amino, aminoC1 3alkyl, aminoC, 3dialkyl, pyrrolidino. piperidino. hexamethyleneimino, piperazino, N-methylpiperazino or morpholino group; R8 represents a hydrogen atom or a C, 4alkyl, C, 4alkoxy, phenyl or amino group; R9 represents a hydrogen atom or a methyl group; R10 represents a methyl, phenyl, amino or dimethylamino group; or P represents a pyridyl group optionally substituted by one or two substitutents selected from halogen atoms or hydroxy, C, 3alkyl and C1 3alkoxy groups. The compounds have a stimulant action at β2-adrenoreceptors and are useful, in particular, in the treatment of diseases associated with reversible airways obstruction such as asthma and chronic bronchitis.

  本发明涉及通式 (I) 的化合物 及其生理上可接受的盐和溶剂 其中 Ar 代表 其中 R3 是键或直链或支链 C1 2 烯基、 R4 是羟基或基团 R5NH，其中 R5 代表基团 CH3SO2-、HCO-或 NH2CO-、 其中 R6 是氯原子或基团 F3C-、 k 代表 1 至 8 的整数、 m 代表零或 2 至 7 的整数，以及 n 代表 2 至 7 的整数，但 k、m 和 n 的总和为 4 至 12； R1 和 R2 各自代表氢原子或甲基或乙基，但 R1 和 R2 中的碳原子总数不超过 2 个； R30 代表氢或 C12 烷基； X 代表氧原子或硫原子 Y 和 Q 可各自代表键或氧原子或硫原子，但条件是 Y 和 Q 中至少有一个代表氧原子或硫原子，当 Y 为键时，m 为零，或当 Y 代表氧原子或硫原子时，m 为 2 至 7 的整数： P 代表可被一个或多个取代基取代的苯基，取代基可选自卤素原子或 C1 3 烷基、C1 3 烷氧基、羟基、-CH2OH-、-(CH2)2OH、-CO2H.-CO2CH3、-CO2(CH2)-2CH3、-R7、COR7、-NHCORs 和 -NR9SO2R10；其中 R7 代表氨基、氨基 C1 3 烷基、氨基 C、3 二烷基、吡咯烷基、哌啶基、六亚甲基亚氨基、哌嗪基、N-甲基哌嗪基或吗啉基； R8 代表氢原子或 C，4-烷基、C，4-烷氧基、苯基或氨基； R9 代表氢原子或甲基 R10 代表甲基、苯基、氨基或二甲基氨基； 或 P 代表吡啶基，可任选被一个或两个选自卤素原子或羟基、C, 3 烷基和 C1 3 烷氧基的取代基取代。 这些化合物对 β2-肾上腺素受体有刺激作用，尤其适用于治疗与可逆性气道阻塞有关的疾病，如哮喘和慢性支气管炎。
• Multi-receptor drug design: Haloperidol as a scaffold for the design and synthesis of atypical antipsychotic agents
  作者：Kwakye Peprah、Xue Y. Zhu、Suresh V.K. Eyunni、Vincent Setola、Bryan L. Roth、Seth Y. Ablordeppey

  DOI：10.1016/j.bmc.2011.12.019

  日期：2012.2

  Using haloperidol as a scaffold, new agents were designed to investigate the structural contributions of various groups to binding at CNS receptors associated with atypical antipsychotic pharmacology. It is clear that each pharmacophoric group, the butyrophenone, the piperidine and the 4-chlorophenyl moieties contributes to changes in binding to the receptors of interest. This strategy has resulted in the identification of several new agents, compounds 16, 18, 19, 23, 24 and 25, with binding profiles which satisfy our stated criteria for agents to act as potential atypical antipsychotics. This research demonstrates that haloperidol can serve as a useful lead in the identification and design of new agents that target multiple receptors associated with antipsychotic pharmacology. Published by Elsevier Ltd.