1-(2-methoxy-5-methylphenyl)-1-phenyl-prop-2-ene-1-ol

• 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: 1-(2-methoxy-5-methylphenyl)-1-phenyl-prop-2-ene-1-ol
• 英文别名: 1-(2-Methoxy-5-methylphenyl)-1-phenylprop-2-en-1-ol
• 化学式: C₁₇H₁₈O₂
• 分子量: 254.329
• InChiKey: ZMMFNMJYYUQUOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  1-(2-methoxy-5-methylphenyl)-1-phenyl-prop-2-ene-1-ol 在 氯化亚砜 、 1,2-bis [(2S,5S)-2,5-diphenylphospholano]ethane 1,5-cyclooctadiene rhodium(I) tetrafluoroborate 、 氢溴酸 、 氢气 、 lithium tert-butoxide 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 、 甲苯 、 乙腈 为溶剂， 20.0~112.0 ℃ 、344.75 kPa 条件下， 反应 26.0h， 生成 托特罗定
  参考文献：
  名称：

  Highly Enantioselective Hydrogenation of Styrenes Directed by 2′-Hydroxyl Groups

  摘要：

  A new synthetic strategy that turns styrene-type olefins into excellent substrates for Rh-catalyzed asymmetric hydrogenation by Installing a 2'-hydroxyl substituent is described. This methodology accommodates trisubstituted olefinic substrates in various E/Z mixtures, leading to valuable benzylic chiral compounds including (R)-tolterodine. It is also demonstrated that the 2'-hydroxyl groups could be readily removed in high yield without loss of ee from the products. Thus, this technology represents an attractive alternative to the Ir(P-N) catalyst system for the asymmetric hydrogenation of unfunctionalized olefins.

  DOI：

  10.1021/ol200422p
• 作为产物：
  描述：

  (2-methoxy-5-methylphenyl)phenylmethanone 、 乙烯基溴化镁 以 四氢呋喃 为溶剂， 生成 1-(2-methoxy-5-methylphenyl)-1-phenyl-prop-2-ene-1-ol
  参考文献：
  名称：

  Highly Enantioselective Hydrogenation of Styrenes Directed by 2′-Hydroxyl Groups

  摘要：

  A new synthetic strategy that turns styrene-type olefins into excellent substrates for Rh-catalyzed asymmetric hydrogenation by Installing a 2'-hydroxyl substituent is described. This methodology accommodates trisubstituted olefinic substrates in various E/Z mixtures, leading to valuable benzylic chiral compounds including (R)-tolterodine. It is also demonstrated that the 2'-hydroxyl groups could be readily removed in high yield without loss of ee from the products. Thus, this technology represents an attractive alternative to the Ir(P-N) catalyst system for the asymmetric hydrogenation of unfunctionalized olefins.

  DOI：

  10.1021/ol200422p

文献信息

• WO2007/39918
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] NOVEL PROCESS FOR THE PREPARATION OF TOLTERODINE<br/>[FR] NOUVEAU PROCEDE DE PREPARATION DE TOLTERODINE
  申请人：NATCO PHARMA LTD

  公开号：WO2007039918A1

  公开（公告）日：2007-04-12

  [EN] The present invention relates to a novel and improved process for the preparation of tolterodine of formula I. Key steps involved in the process are a vinyl Grignard reaction on a benzophenone derivative of formula XXI to get the vinyl carbinol derivative of formula XXII and rearrangement of the carbinol derivative to an allylic alcohol derivative of formula XXIII to get the required carbon framework. Compound of formula XXIII is further converted to tolterodine in four steps. Tolterodine is a muscarinic receptor antagonist useful in treatment of urinary urge incontinence and other symptoms of bladder over activity.
  [FR] La présente invention concerne un procédé nouveau et amélioré de préparation de toltérodine représentée par la formule (I). Les étapes clés intervenant dans le procédé sont: une réaction Grignard de vinyle sur un dérivé de benzophénone représenté par la formule XXI pour obtenir le dérivé de carbinol de vinyle représenté par la formule XXII et le réarrangement du dérivé de carbinol en un dérivé d'alcool allylique représenté par la formule XXIII pour obtenir la structure de carbone requise. Le composé de la formule XXIII est ensuite converti en toltérodine en quatre étapes. La toltérodine est un antagoniste du récepteur muscarinique utilisé dans le traitement de l'incontinence urinaire d'urgence et d'autres symptômes liés à la suractivité de la vessie.
• Highly Enantioselective Hydrogenation of Styrenes Directed by 2′-Hydroxyl Groups
  作者：Xiang Wang、Anil Guram、Seb Caille、Jack Hu、J P. Preston、Michael Ronk、Shawn Walker

  DOI：10.1021/ol200422p

  日期：2011.4.1

  A new synthetic strategy that turns styrene-type olefins into excellent substrates for Rh-catalyzed asymmetric hydrogenation by Installing a 2'-hydroxyl substituent is described. This methodology accommodates trisubstituted olefinic substrates in various E/Z mixtures, leading to valuable benzylic chiral compounds including (R)-tolterodine. It is also demonstrated that the 2'-hydroxyl groups could be readily removed in high yield without loss of ee from the products. Thus, this technology represents an attractive alternative to the Ir(P-N) catalyst system for the asymmetric hydrogenation of unfunctionalized olefins.