3-(2-benzyloxy-5-methylphenyl)-3-phenylpropanol | 854306-68-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(2-benzyloxy-5-methylphenyl)-3-phenylpropanol
• 英文别名: 3-(2-benzyloxy-5-methyl-phenyl)-3-phenyl-propan-1-ol；3-(5-methyl-2-phenylmethoxyphenyl)-3-phenylpropan-1-ol
• CAS: 854306-68-6
• 化学式: C₂₃H₂₄O₂
• 分子量: 332.442
• InChiKey: RKLIBBRRUITMAB-UHFFFAOYSA-N

物化性质

• 沸点：
  509.9±38.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-benzyloxy-5-methylphenyl)-3-phenylpropanol 在 盐酸 、 4-二甲氨基吡啶 、 palladium on activated charcoal 、 氢气 、 sodium carbonate 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 40.5h， 生成 (R)-托特罗定L-酒石酸盐
  参考文献：
  名称：

  Ligand–Phospholipid Conjugation: A Versatile Strategy for Developing Long-Acting Ligands That Bind to Membrane Proteins by Restricting the Subcellular Localization of the Ligand

  摘要：

  We hypothesized that if drug localization can be restricted to a particular subcellular domain where their target proteins reside, the drugs could bind to their target proteins without being metabolized and/or excreted, which would significantly extend the half-life of the corresponding drug target complex. Thus, we designed ligand phospholipid conjugates in which the ligand is conjugated with a phospholipid through a polyethylene glycol linker to restrict the subcellular localization of the ligand in the vicinity of the lipid bilayer. Here, we present the design, synthesis, pharmacological activity, and binding mode analysis of ligand phospholipid conjugates with muscarinic acetylcholine receptors as the target proteins. These results demonstrate that ligand phospholipid conjugation can be a versatile strategy for developing long-acting ligands that bind to membrane proteins in drug discovery.

  DOI：

  10.1021/acs.jmedchem.8b00041
• 作为产物：
  描述：

  溴甲苯 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 6.0h， 生成 3-(2-benzyloxy-5-methylphenyl)-3-phenylpropanol
  参考文献：
  名称：

  Ligand–Phospholipid Conjugation: A Versatile Strategy for Developing Long-Acting Ligands That Bind to Membrane Proteins by Restricting the Subcellular Localization of the Ligand

  摘要：

  We hypothesized that if drug localization can be restricted to a particular subcellular domain where their target proteins reside, the drugs could bind to their target proteins without being metabolized and/or excreted, which would significantly extend the half-life of the corresponding drug target complex. Thus, we designed ligand phospholipid conjugates in which the ligand is conjugated with a phospholipid through a polyethylene glycol linker to restrict the subcellular localization of the ligand in the vicinity of the lipid bilayer. Here, we present the design, synthesis, pharmacological activity, and binding mode analysis of ligand phospholipid conjugates with muscarinic acetylcholine receptors as the target proteins. These results demonstrate that ligand phospholipid conjugation can be a versatile strategy for developing long-acting ligands that bind to membrane proteins in drug discovery.

  DOI：

  10.1021/acs.jmedchem.8b00041

文献信息

• PROCESS FOR PREPARATION OF PHENOLIC MONOESTERS OF HYDROXYMETHYL PHENOLS
  申请人：DESAI Sanjay Jagdish

  公开号：US20110282094A1

  公开（公告）日：2011-11-17

  A process for the preparation of phenolic monoesters of 2-(3-diisopropylamino-1-phenylpropyl)-4-(hydroxymethyl)phenol by converting (±)6-halo-4-phenylchroman-2-one to (±)4-halo-2-(3-hydroxy-1-phenylpropyl)phenol. The two hydroxyl groups are protected and the protected compound is reacted with diisopropylamine to give (±)[3-(2-benzyloxy-5-halophenyl)-3-phenylpropyl]diisopropylamine. The halo substituent on the benzene ring is converted to corresponding benzyl alcohol and then the protection is removed to give racemic 5-HMT. Racemic 5-HMT is converted R enantiomer and then it is esterified.

  一种制备2-(3-二异丙基氨基-1-苯基丙基)-4-(羟甲基)酚的酚单酯的方法，通过将(±)6-卤代-4-苯基色苷-2-酮转化为(±)4-卤代-2-(3-羟基-1-苯基丙基)酚。两个羟基团被保护，保护化合物与二异丙基胺反应，得到(±)[3-(2-苄氧基-5-卤苯基)-3-苯基丙基]二异丙基胺。苯环上的卤代取代基被转化为相应的苄醇，然后去除保护作用，得到外消旋的5-HMT。外消旋的5-HMT转化为R对映体，然后酯化。
• Process for the Preparation of Fesoterodine
  申请人：Charugundla Kishore

  公开号：US20100217034A1

  公开（公告）日：2010-08-26

  Disclosed herein is an improved, commercially viable and industrially advantageous process for the preparation of Fesoterodine or a pharmaceutically acceptable salt thereof in high yield and purity. Disclosed also herein is an improved and industrially advantageous optical resolution method of racemic (±)-N,N-Diisopropyl-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropylamine and use thereof for the preparation of Fesoterodine.

  本文披露了一种改进的、商业可行的和工业上有利的制备Fesoterodine或其药用可接受盐的过程，其产率高且纯度高。本文还披露了一种改进的和工业上有利的光学分辨方法，用于制备Fesoterodine的混合对映体（±）-N，N-二异丙基-3-（2-苄氧基-5-溴苯基）-3-苯基丙胺及其应用。
• Process for the preparation of N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propaneamine
  申请人：Turchetta Stefano

  公开号：US20060079716A1

  公开（公告）日：2006-04-13

  A process is described for the preparation of N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propaneamine comprising substitution of the sulfonyloxy group of the compound of the formula in which the substituents R and R″ have the meanings stated in the description, in a solvent comprising an ionic liquid, to yield the tertiary amine of the formula and the subsequent deprotection thereof.

  描述了一种制备N，N-二异丙基-3-(2-羟基-5-甲基苯基)-3-苯基-丙胺的过程，包括在含有离子液体的溶剂中，通过替代具有所述描述中所述的R和R″含义的化合物的磺酰氧基来产生该化合物的三级胺，以及随后的去保护步骤。
• [EN] TOLTERODINE, COMPOSITIONS AND USES THEREOF, AND PREPARATION OF THE SAME<br/>[FR] TOLTERODINE, COMPOSITIONS ET LEURS UTILISATIONS, ET PREPARATIONS DESDITES COMPOSITIONS
  申请人：CIPLA LTD

  公开号：WO2005061432A1

  公开（公告）日：2005-07-07

  Racemic tolterodine free base in crystalline form, tolterodine with improved purity, compositions and uses thereof, and processes of preparing the same.

  左托吡啶盐酸盐的晶体形式，提高纯度的左托吡啶，其组合物和用途，以及制备这些物质的过程。
• Process for preparing tolterodine
  申请人：Venkataraman Sundaram

  公开号：US20060094904A1

  公开（公告）日：2006-05-04

  A process for preparing tolterodine with high purity.

  一种制备高纯度托特罗定的方法。