4-[2-(环丙基甲氧基)乙基]苯酚 | 63659-16-5

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 4-[2-(环丙基甲氧基)乙基]苯酚
• 英文名称: 4-[2-(cyclopropylmethoxy)-ethyl]-phenol
• 英文别名: 4-<2-(cyclopropylmethoxy)ethyl>phenol；4-<(cyclopropylmethoxy)ethyl>phenol；para-[2-(cyclopropylmethoxy)ethyl] phenol；4-(2-cyclopropylmethoxyethyl)phenol；p-cyclopropylmethyloxyethylphenol；4-[2-(cyclopropylmethoxy)ethyl]phenol
• CAS: 63659-16-5
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: WNEQFDSWDCYKOE-UHFFFAOYSA-N

物化性质

• 沸点：
  304.4±17.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2909500000

制备方法与用途

用途：用于制备医药中间体。

反应信息

• 作为反应物：
  描述：

  4-[2-(环丙基甲氧基)乙基]苯酚 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 60.0h， 生成 倍他索洛尔
  参考文献：
  名称：

  Synthesis of a series of compounds related to betaxolol, a new .beta.1-adrenoceptor antagonist with a pharmacological and pharmacokinetic profile optimized for the treatment of chronic cardiovascular diseases

  摘要：

  A series of para-substituted phenoxypropanolamines has been synthesized and tested for beta-adrenoceptor blocking activity. Some derivatives (8, 11, 12, 20, 21) exhibited greater in vitro potency than the reference drugs metoprolol and propranolol. This series, in contrast to propranolol but similar to metoprolol, possesses cardioselectivity. The 3-[p-[(cycloalkylmethoxy)ethyl]phenoxy]-1-substituted-amino-2-prop anol derivatives 8 (cyclopropylmethoxyethyl: betaxolol) and 11 (cyclobutylmethoxyethyl) produced antihypertensive effects in spontaneously hypertensive rats. Betaxolol (Kerlon, 8) was found to exhibit an appropriate preclinical pharmacological and human pharmacokinetic profile (elevated oral bioavailability and prolonged plasma half-life) for the treatment of chronic cardiovascular diseases such as hypertension and angina.

  DOI：

  10.1021/jm00389a008
• 作为产物：
  描述：

  2-(4-苯甲氧基苯基)乙醇 在 potassium tert-butylate 、 氢气 、 diethylzinc 、 镍 作用下， 以 甲醇 、 正己烷 、 二甲基亚砜 为溶剂， 40.0 ℃ 、448.16 kPa 条件下， 反应 13.0h， 生成 4-[2-(环丙基甲氧基)乙基]苯酚
  参考文献：
  名称：

  A convenient synthesis of the enantiomerically pure β-blocker (S)-betaxolol using hydrolytic kinetic resolution

  摘要：

  Enantiopure (S)-betaxolol was prepared in an extremely simple and practical way using hydrolytic kinetic resolution of a terminal epoxide by Jacobsen's catalyst. High enantiomeric purity (99% ee) has been achieved and the method is amenable to industrial scale-up. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.028
• 作为试剂：
  描述：

  4-[2-(环丙基甲氧基)乙基]苯酚 、 在 4-[2-(环丙基甲氧基)乙基]苯酚 作用下， 生成
  参考文献：
  名称：

  J. Med. Chem. 1987, 30, 1003-1011

  摘要：

  DOI：

文献信息

• [EN] DIARYLAMIDE-SPIRODIAMINE DERIVATIVE<br/>[FR] DÉRIVÉ DE DIARYLAMIDE-SPIRODIAMINE
  申请人：BANYU PHARMA CO LTD

  公开号：WO2010147234A1

  公开（公告）日：2010-12-23

  To provide a melanin concentrating hormone receptor antagonist useful as medicines for central system disorders, cardiovascular disorders and metabolic disorders. Provided is a compound of a formula (I): wherein R1a and R1b each are a hydrogen atom, etc.; R2 is a hydrogen atom, a C1-6 alkyl, etc.; Ar1 is a 6-membered aromatic carbocyclic group or a 6-membered aromatic nitrogen-containing heterocyclic group; Ar2 is a group to be formed by removing two hydrogen atoms from a 6-membered aromatic carbon ring, a 6-membered aromatic nitrogen-containing hetero ring, etc.; Ar3 is a mono- or bi-cyclic aromatic carbocyclic group or aromatic heterocyclic group; m1, m2, m3 and m4 are independently 0, 1, 2, 3 or 4, provided that the total of m1 and m2 is from 2 to 6, and the total of m3 and m4 is from 2 to 6. The compound is useful as medicines for central system disorders, cardiovascular disorders and metabolic disorders.

  提供一种黑色素浓缩激素受体拮抗剂，用作治疗中枢系统疾病、心血管疾病和代谢性疾病的药物。提供的化合物具有如下结构（I）：其中R1a和R1b分别是氢原子等；R2是氢原子、C1-6烷基等；Ar1是6元芳香碳环基团或6元芳香氮杂环基团；Ar2是由6元芳香碳环中去除两个氢原子形成的基团，或者是6元芳香氮杂环等；Ar3是单环或双环芳香碳环基团或芳香杂环基团；m1、m2、m3和m4独立地为0、1、2、3或4，要求m1和m2的总和为2到6，m3和m4的总和为2到6。该化合物可用作治疗中枢系统疾病、心血管疾病和代谢性疾病的药物。
• Design and synthesis of a series of combined vasodilator-.beta.-adrenoceptor antagonists based on 6-arylpyridazinones
  作者：R. A. Slater、W. Howson、G. T. G. Swayne、E. M. Taylor、D. R. Reavill

  DOI：10.1021/jm00397a013

  日期：1988.2

  synthesized and evaluated as combined vasodilator/beta-adrenoceptor antagonists and potential antihypertensive agents. Many of the early compounds displayed an unacceptably high level of intrinsic sympathomimetic activity (ISA) and a relatively short duration of action. Disubstitution in the 2,3-positions or in the 4-position of the aryloxy ring gave compounds with low ISA levels and, in some instances,

  已经合成了一系列新的6- [4-[[（（芳氧基）酰基]氨基]苯基] -4,5-二氢吡啶并酮，并被评估为血管扩张剂/β-肾上腺素能受体拮抗剂和潜在的降压药。许多早期化合物显示出高水平的固有拟交感神经活性（ISA）和相对较短的作用时间。在芳氧基环的2，3-位或4-位二取代得到的化合物具有较低的ISA水平，并且在某些情况下改善了作用时间。所有这些化合物都是血管扩张药，但5-甲基哒嗪酮衍生物的抗高血压活性始终高于其5-H较低的同系物。
• Selective Terminal Heck Arylation of Vinyl Ethers with Aryl Chlorides:  A Combined Experimental−Computational Approach Including Synthesis of Betaxolol
  作者：Gopal K. Datta、Henrik von Schenck、Anders Hallberg、Mats Larhed

  DOI：10.1021/jo0602367

  日期：2006.5.1

  medium. The selectivity for linear β-product in PEG-200 is slightly higher than in aqueous DMF. DFT calculations support a ligand-driven selectivity rationale, where the electronic and steric influence of bulky P(t-Bu)3 ligand provides improved β-selectivity in the essential insertion step also with electron-rich aryl chlorides. A tentative computational rationalization of the improved selectivity in non-methylated

  反应条件对于具有高的区域选择性非环状乙烯基醚类的钯催化的终端（β-）芳基化使用廉价的芳基氯作为原料，和P（已开发吨-Bu）3释放preligand [（吨-Bu 3）PH] BF 4作为关键添加剂。这种快速而直接的方案利用了非惰性条件和受控的微波加热，以最大程度地减少了处理和加工时间，并使用了DMF水溶液或环保型PEG-200作为反应介质。PEG-200中线性β产物的选择性略高于水性DMF。DFT计算支持配体驱动的选择性原理，其中大体积P（t-Bu）3配体在必要的插入步骤中也利用富电子的芳基氯化物提供了改进的β-选择性。讨论了在非甲基化PEG中提高选择性的初步计算合理性。最后，该合成方法被用于从对硝基苯氯（一种合成β-肾上腺素阻断剂倍他洛尔的关键中间体）中有效地获得直链对-[2-（环丙基甲氧基）乙基]苯酚。
• Vasodilators and .beta.-adrenoceptor antagonists
  申请人：Smith Kline & French Laboratories Ltd.

  公开号：US04652563A1

  公开（公告）日：1987-03-24

  This invention relates to dihydropyridazinone compounds having a cyclopropylmethoxyethyl group in the 6-substituent. These compounds are vasodilators and .beta.-adrenoceptor antagonists. A particular compound of the invention is 6-[4-[3-[2-hydroxy-3-[4-(2-(cyclopropylmethoxy) ethyl)phenoxy]propylamino]propionamido]phenyl]-5-methyl-4,5-dihydro-3 (2H)-pyridazinone.

  这项发明涉及具有6-取代物中环丙基甲氧乙基基团的二氢吡啶基酮化合物。这些化合物是血管扩张剂和β-肾上腺素受体拮抗剂。该发明的一种特定化合物是6-[4-[3-[2-羟基-3-[4-(2-(环丙基甲氧基)乙基)苯氧基]丙基氨基]丙酰氨基]苯基]-5-甲基-4,5-二氢-3(2H)-吡啶酮。
• PROCESS FOR PREPARATION OF S-(-)-BETAXOLOL AND SALTS THEREOF
  申请人：Joshi Anna Ramesh

  公开号：US20060004109A1

  公开（公告）日：2006-01-05

  The present invention relates to an improved process for preparation of S-(−)-betaxolol salts. More particularly the present invention relates to the preparation of hydrochloride salt of S-(−)-betaxolol of formula (1).

  本发明涉及一种改进的制备S-(−)-贝他索洛盐的方法。更具体地，本发明涉及制备S-(−)-贝他索洛的盐酸盐，化学式为(1)。