4-(4-(2-(isochroman-1-yl)ethyl)-piperazin-1-yl)benzenesulfonamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-(4-(2-(isochroman-1-yl)ethyl)-piperazin-1-yl)benzenesulfonamide
• 英文别名: (+)-sonepiprazole；(R)-(+)-4-[4-[2-(isochroman-1-yl)ethyl]piperazin-1-yl]benzenesulfonamide；4-[4-((R)-2-Isochroman-1-yl-ethyl)-piperazin-1-yl]-benzenesulfonamide；4-[4-[2-[(1R)-3,4-dihydro-1H-isochromen-1-yl]ethyl]piperazin-1-yl]benzenesulfonamide
• 化学式: C₂₁H₂₇N₃O₃S
• 分子量: 401.53
• InChiKey: WNUQCGWXPNGORO-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  异色满 在 lithium aluminium tetrahydride 、 叔丁基锂 、 三乙胺 、 (4S,4′S)-(-)-2,2′-(3-戊烯基)双(4-异丙基噁唑啉) 作用下， 以 正己烷 为溶剂， 反应 2.5h， 生成 4-(4-(2-(isochroman-1-yl)ethyl)-piperazin-1-yl)benzenesulfonamide
  参考文献：
  名称：

  External chiral ligand-induced enantioselective lithiation/SE2 reactions of isochroman and phthalan

  摘要：

  Treatment of isochroman and phthalan with a t-BuLi/chiral bis(oxazoline) complex followed by reaction with carbon-electrophiles such as benzaldehyde and CO2 is shown to afford the a-substituted derivatives in moderate-to-high enantioselectivities (up to 97% ee and 83% ee, respectively). The asymmetric induction is proved to occur at the post-lithiation step. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01028-5

文献信息

• Heterocyclic compounds for the treatment of CNS and cardiovascular
  申请人：Pharmacia & Upjohn Company

  公开号：US05877317A1

  公开（公告）日：1999-03-02

  Novel aromatic bicyclic amines of formula (I) ##STR1## are useful in treating central nervous system disorders and cardiac arrhythmias and cardiac fibrillation.

  新型芳香族双环胺化合物的化学式（I）##STR1## 在治疗中枢神经系统疾病、心律失常和心房颤动方面具有用处。
• [EN] HETEROCYCLIC COMPOUNDS FOR THE TREATMENT OF CNS AND CARDIOVASCULAR DISORDERS<br/>[FR] COMPOSES HETEROCYCLIQUES POUR LE TRAITEMENT DES TROUBLES DU SYSTEME NERVEUX CENTRAL ET DES TROUBLES CARDIOVASCULAIRES
  申请人：THE UPJOHN COMPANY

  公开号：WO1995018118A1

  公开（公告）日：1995-07-06

  (EN) Novel aromatic bicyclic amines of formula (I) are useful in treating central nervous system disorders and cardiac arrhythmias and cardiac fibrillation.(FR) L'invention concerne de nouvelles amines bicycliques aromatiques de formule (I) destinées à être utilisées pour le traitement des troubles du système nerveux central, des arythmies cardiaques et de la fibrillation cardiaque.

  (中) 公式（I）的新型芳香族双环胺在治疗中枢神经系统疾病、心律失常和心房颤动方面具有用途。
• (<i>S</i>)-(−)-4-[4-[2-(Isochroman-1-yl)ethyl]piperazin-1-yl]benzenesulfonamide, a Selective Dopamine D₄ Antagonist
  作者：Ruth E. TenBrink、Carol L. Bergh、J. Neil Duncan、Douglas W. Harris、R. M. Huff、Robert A. Lahti、Charles F. Lawson、Barry S. Lutzke、Iain J. Martin、Susan A. Rees、Siusaidh K. Schlachter、John C. Sih、Martin W. Smith

  DOI：10.1021/jm960084f

  日期：1996.1.1
• Organocatalytic, Enantioselective Synthesis of 1- and 3-Substituted Isochromans via Intramolecular Oxa-Michael Reaction of Alkoxyboronate: Synthesis of (+)-Sonepiprazole
  作者：Barnala Ravindra、Sanjay Maity、Braja Gopal Das、Prasanta Ghorai

  DOI：10.1021/acs.joc.5b00719

  日期：2015.7.17

  The enantioselective oxa-Michael reaction of alkoxyboronate strategy was demonstrated to provide a new and practical route to enantioriched 1- and 3-substituted isochromans using a chiral bifunctional organocatalyst. Furthermore, this methodology was extended to the enantioselective synthesis of (+)-sonepiprazole, a dopamine receptor antagonist.
• HETEROCYCLIC COMPOUNDS FOR THE TREATMENT OF CNS AND CARDIOVASCULAR DISORDERS
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：EP0737189B1

  公开（公告）日：1999-07-28