(1R,2R)-2-(4-phenylpiperazin-1-yl)-1,2-dihydronaphthalen-1-ol | 1235703-66-8

• 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: (1R,2R)-2-(4-phenylpiperazin-1-yl)-1,2-dihydronaphthalen-1-ol
• 英文别名: (1R,2R)-2-(4-phenylpiperidin-1-yl)-1,2-dihydronaphthalen-1-ol
• CAS: 1235703-66-8
• 化学式: C₂₀H₂₂N₂O
• 分子量: 306.407
• InChiKey: FZVLCCPRAPSSPJ-WOJBJXKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,4-二氢-1,4-环氧萘 、 N-苯基哌嗪 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 碘化铵 、 PPF-P(t-Bu)2 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以95%的产率得到(1R,2R)-2-(4-phenylpiperazin-1-yl)-1,2-dihydronaphthalen-1-ol
  参考文献：
  名称：

  高效铑催化的氧杂苯并降冰片二烯与胺亲核试剂的不对称开环反应

  摘要：

  研究了铑催化的氧杂苯并降冰片二烯与脂肪族伯胺和取代的 N-苯基哌嗪的不对称开环反应。这些反应的特点是通过桥头氧与胺亲核试剂的分子间烯丙基置换形成新的碳 - 氮键，这提供了相应的产品，收率良好（高达 97%）和优异的对映选择性（高达 99 %ee).图形摘要研究了铑催化的氧杂苯并降冰片二烯与脂肪族伯胺和取代的N-苯基哌嗪的不对称开环反应。这些反应的特点是通过桥头氧与胺亲核试剂的分子间烯丙基置换形成新的碳氮键，

  DOI：

  10.1007/s10562-010-0383-3

文献信息

• Iridium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with N-Substituted Piperazine Nucleophiles
  作者：Wen Yang、Renshi Luo、Dingqiao Yang

  DOI：10.3390/molecules201219748

  日期：——

  Iridium-catalyzed asymmetric ring-opening of oxabenzonorbornadienes with N-substituted piperazines was described. The reaction afforded the corresponding ring-opening products in high yields and moderate enantioselectivities in the presence of 2.5 mol % [Ir(COD)Cl]2 and 5.0 mol % (S)-p-Tol-BINAP. The effects of various chiral bidentate ligands, catalyst loading, solvent, and temperature on the yield and enantioselectivity were also investigated. A plausible mechanism was proposed to account for the formation of the corresponding trans-ring opened products based on the X-ray structure of product 2i.

  报道了铱催化的氧杂苯并降冰片二烯与N-取代哌嗪的不对称开环反应。在2.5 mol% [Ir(COD)Cl]2和5.0 mol% (S)-对甲苯-BINAP的存在下，该反应以高产率和中等对映选择性提供了相应的开环产物。还研究了各种手性双齿配体、催化剂用量、溶剂和温度对产率和对映选择性的影响。基于产物2i的X射线结构，提出了一个合理的机理来解释相应反式开环产物的形成。
• Asymmetric ring-opening of oxabenzonorbornadiene with amines promoted by a chiral iridium-monophosphine catalyst
  作者：Renshi Luo、Jianhua Liao、Ling Xie、Wenjun Tang、Albert S. C. Chan

  DOI：10.1039/c3cc46009f

  日期：——

  A new iridium-monophosphine catalyst is found to be efficient for asymmetric ring-opening of benzonorbornadiene with amines, providing a series of chiral substituted dihydronaphthalenes in high yields (up to 98%) and excellent enantioselectivities (>99%).

  发现一种新的铱单膦催化剂可有效地使苯并降冰片二烯与胺发生不对称开环，从而以高收率（高达98％）和出色的对映选择性（> 99％）提供一系列手性取代的二氢萘。
• Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles
  作者：Dingqiao Yang、Ping Hu、Yuhua Long、Yujuan Wu、Heping Zeng、Hui Wang、Xiongjun Zuo

  DOI：10.3762/bjoc.5.53

  日期：——

  Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with various aliphatic and aromatic secondary amines are reported for the first time. The reaction gave the corresponding trans-1,2-dihydronaphthalenol derivatives in good yields with moderate enantioselectivities in the presence of 2.5 mol % [Ir(COD)Cl](2) and 5 mol % bisphosphine ligand (S)-p-Tol-BINAP. The trans-configuration

  首次报道了铱催化的氧杂环烯烃与各种脂肪族和芳香族仲胺的不对称开环反应。在 2.5 mol% [Ir(COD)Cl](2) 和 5 mol% 双膦配体 (S)-p-Tol-比纳普。X 射线晶体学证实了 3f 的反式构型。
• Rhodium-catalyzed asymmetric ring opening reaction of oxabenzonorbornadienes with amines using ZnI₂ as the activator
  作者：Xin Xu、Jingchao Chen、Zhenxiu He、Yongyun Zhou、Baomin Fan

  DOI：10.1039/c5ob02331a

  日期：——

  [Rh(COD)Cl]2 and (R,R)-BDPP was used as an effective catalyst for the asymmetric ring opening reaction of oxabenzonorbornadienes with various amines by employing ZnI2 as the activator. Under the optimized reaction conditions, high enantioselectivities with good yields could be obtained from a wide scope of oxabenzonorbornadienes and amines.

  [Rh（COD）Cl] 2和（R，R）-BDPP的配合物通过使用ZnI 2作为活化剂，用作氧杂苯并降冰片二烯与各种胺的不对称开环反应的有效催化剂。在优化的反应条件下，可以从各种范围的草酰苯并降冰片二烯和胺中获得高对映选择性，并具有良好的收率。
• Iridium-catalyzed highly enantioselective ring opening reaction of oxabenzonorbornadienes with amines
  作者：Yongyun Zhou、Zhiwu Lu、Baiqiu Han、Chaoyuan Zeng、Zhenhua Zhang、Baomin Fan

  DOI：10.1016/j.tetasy.2015.10.017

  日期：2015.12

  The complex of [Ir(COD)Cl](2) and (R)-xylyl-phanephos was used as an effective catalyst for the asymmetric ring opening reaction of oxabenzonorbomadienes with various amines. Under the optimized reaction conditions, high enantioselectivities with moderate to good yields could be obtained from a wild scope of oxabenzonorbornadienes and amines. (C) 2015 Elsevier Ltd. All rights reserved.