2-(2-phenoxyethoxy)ethyl methanesulfonate | 86902-13-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(2-phenoxyethoxy)ethyl methanesulfonate
• CAS: 86902-13-8
• 化学式: C₁₁H₁₆O₅S
• 分子量: 260.311
• InChiKey: YPSHOERJJFCIRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[2-羟基-3-(丙-2-基氨基)丙氧基]苯酚 、 2-(2-phenoxyethoxy)ethyl methanesulfonate 在 sodium hydride 作用下， 生成 1-[4-[2-(2-Phenoxyethoxy)ethoxy]phenoxy]-3-(propan-2-ylamino)propan-2-ol
  参考文献：
  名称：

  .beta.1-Selective adrenoceptor antagonists. 2. 4-Ether-linked phenoxypropanolamines

  摘要：

  A series of 4-substituted phenoxypropanolamines was prepared and examined for beta-adrenoceptor activity. Some of the compounds, especially the [4-[2-[[2-(4-fluorophenyl)ethyl] oxy]ethoxy]phenoxy]propanolamines (14, 15, and 24), showed potent beta 1-blockade with virtually no beta 2-blockade at doses over a 1000 times greater. The compounds also possessed partial agonist activity. Structure-activity relationships are discussed, and conclusions are drawn about the binding sites on beta-adrenoceptors.

  DOI：

  10.1021/jm00365a005
• 作为产物：
  描述：

  二乙二醇二甲烷磺酸酯 、 苯酚 在 sodium hydride 作用下， 生成 2-(2-phenoxyethoxy)ethyl methanesulfonate
  参考文献：
  名称：

  .beta.1-Selective adrenoceptor antagonists. 2. 4-Ether-linked phenoxypropanolamines

  摘要：

  A series of 4-substituted phenoxypropanolamines was prepared and examined for beta-adrenoceptor activity. Some of the compounds, especially the [4-[2-[[2-(4-fluorophenyl)ethyl] oxy]ethoxy]phenoxy]propanolamines (14, 15, and 24), showed potent beta 1-blockade with virtually no beta 2-blockade at doses over a 1000 times greater. The compounds also possessed partial agonist activity. Structure-activity relationships are discussed, and conclusions are drawn about the binding sites on beta-adrenoceptors.

  DOI：

  10.1021/jm00365a005

文献信息

• [EN] BENZENESULPHONAMIDES AND PROCESS FOR THEIR PREPARATION<br/>[FR] BENZENESULPHONAMIDES ET PROCEDES D'ELABORATION CORRESPONDANTS
  申请人：RICHTER GEDEON VEGYESZET

  公开号：WO2004022532A1

  公开（公告）日：2004-03-18

  New process for industrial preparation of R-(-)-tamsulosine HCl of formula (I). In this process (R,S)-5-[2-(N-benzyl-amino)-propyl]-2-methoxy-benzenesulphonamide of formula (I), acid addition salts and enantiomers thereof and R-5-[2-[N-(2-ethoxy-phenoxy)-ethyl]-N-benzyl]-amino]-propyl-2-methoxy-benzenesulphonamide of formula (III) are new intermediates. R-(-)-tamsulosine HCl of formula (I) is prepared by reacting the secondary benzylamine of formula (II) with an alkylating agent to R-5-[2-[N-(2-ethoxy-phenoxy)-ethyl]-N-benzyl]-amino]-propyl-2-methoxy-benzenesulphonamide of formula (III), the benzyl protecting group is removed and then HCl salt is formed. The optically active compound of formula (II) is prepared by reductive condensation of (4-methoxy-3-sulphamoyl-phenyl)-acetone and benzylamine and the obtained racemic compound is optically resolved by chiral acid.

  工业制备R-(-)-坦索洛辛盐酸盐的新工艺。在这个工艺中，公式（I）的（R,S）-5-[2-(N-苄基氨基)-丙基]-2-甲氧基苯磺酰胺、其酸盐和对映体以及公式（III）的R-5-[2-[N-(2-乙氧基-苯氧基)-乙基]-N-苄基]-氨基]-丙基-2-甲氧基苯磺酰胺是新的中间体。通过将公式（II）的二苄胺与烷基化剂反应制备公式（III）的R-5-[2-[N-(2-乙氧基-苯氧基)-乙基]-N-苄基]-氨基]-丙基-2-甲氧基苯磺酰胺，然后去除苄保护基形成HCl盐，从而制备公式（I）的R-(-)-坦索洛辛盐酸盐。通过对（4-甲氧基-3-磺胺基苯基）-丙酮和苄胺进行还原缩合制备公式（II）的光学活性化合物，然后通过手性酸对得到的外消旋化合物进行光学分离。
• MACHIN, P. J.;HURST, D. N.;BRADSHAW, R. M.;BLABER, L. C.;BURDEN, D. T.;FR+, J. MED. CHEM., 1983, 26, N 11, 1570-1576
  作者：MACHIN, P. J.、HURST, D. N.、BRADSHAW, R. M.、BLABER, L. C.、BURDEN, D. T.、FR+

  DOI：——

  日期：——
• BENZENESULPHONAMIDES AND PROCESS FOR THEIR PREPARATION
  申请人：RICHTER GEDEON VEGYESZETI GYAR R.T.

  公开号：EP1539684A1

  公开（公告）日：2005-06-15
• .beta.1-Selective adrenoceptor antagonists. 2. 4-Ether-linked phenoxypropanolamines
  作者：Peter J. Machin、David N. Hurst、Rachel M. Bradshaw、Leslie C. Blaber、David T. Burden、Allison D. Fryer、Rosemary A. Melarange、Celia Shivdasani

  DOI：10.1021/jm00365a005

  日期：1983.11

  A series of 4-substituted phenoxypropanolamines was prepared and examined for beta-adrenoceptor activity. Some of the compounds, especially the [4-[2-[[2-(4-fluorophenyl)ethyl] oxy]ethoxy]phenoxy]propanolamines (14, 15, and 24), showed potent beta 1-blockade with virtually no beta 2-blockade at doses over a 1000 times greater. The compounds also possessed partial agonist activity. Structure-activity relationships are discussed, and conclusions are drawn about the binding sites on beta-adrenoceptors.