(1R,2R)-2-(phenylamino)-1,2-dihydronaphthalen-1-ol | 1239667-69-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R,2R)-2-(phenylamino)-1,2-dihydronaphthalen-1-ol
• 英文别名: (1R,2R)-2-anilino-1,2-dihydronaphthalen-1-ol
• CAS: 1239667-69-6
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: FGCAUBSLACVXMM-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,4-epoxy-1,4-dihydronaphthalene 、 苯胺 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 (2R,4R)-(+)-2,4-双(二苯基磷)戊烷 、 zinc(II) iodide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.27h， 以95%的产率得到(1R,2R)-2-(phenylamino)-1,2-dihydronaphthalen-1-ol
  参考文献：
  名称：

  使用ZnI 2作为活化剂，铑催化草酸苯并降冰片二烯与胺的不对称开环反应†

  摘要：

  [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。

  DOI：

  10.1039/c5ob02331a

文献信息

• Iridium-Catalyzed Asymmetric Ring-Opening Reactions of Oxabenzonorbornadienes with Amine Nucleophiles
  作者：Dingqiao Yang、Yuhua Long、Junfang Zhang、Heping Zeng、Sanyong Wang、Chunrong Li

  DOI：10.1021/om100384q

  日期：2010.8.23

  We have explored a new iridium-catalyzed ring-opening reaction of oxabenzonorbornadienes with a variety of primary aromatic amine or N-substituted piperazine nucleophiles, affording the corresponding products in excellent yields (up to 99%) with moderate enantioselectivity (25−81% ee). The trans configuration of product 2d was confirmed by X-ray crystallography.

  我们探索了氧杂苯并降冰片二烯与各种伯芳族胺或N-取代的哌嗪亲核试剂的铱催化开环反应，从而以中等收率（25-81％ee）以优异的收率（高达99％）提供了相应的产物）。通过X射线晶体学确认产物2d的反式构型。
• Chiral NHC-Iridium Complexes and Their Performance in Enantioselective Intramolecular Hydroamination and Ring-Opening Amination Reactions
  作者：Pengchao Gao、Daven Foster、Gellért Sipos、Brian W. Skelton、Alexandre N. Sobolev、Reto Dorta

  DOI：10.1021/acs.organomet.9b00770

  日期：2020.2.24

  More importantly, the catalyst performance of these chiral cationic NHC-iridium complexes was expanded to the enantioselective ring-opening aminations of oxabicycles, where a highly enantioselective catalyst system was identified. Furthermore, we discovered that using the opposite axial stereochemistry on the NHC ligand completely switched the absolute configuration of the product, again showing high

  一系列带有TFB（四氟苯并戊烯基），TCB（四氯苯并戊烯基），BB（苯并戊烯基）和COD（环辛二烯）的通式[（NHC *）Ir（二烯）Cl]的手性N-杂环卡宾（NHC）-铱配合物合成并充分表征了二烯配体。所用的手性NHC配体是我们小组先前报道的类型，具有骨架立体中心和轴向手性。阳离子NHC-铱配合物[（NHC *）Ir（二烯）] [PF 6 ]是通过用AgPF 6从[（NHC *）Ir（二烯）Cl]氯化物提取而获得的。。获得并分析了一些中性和阳离子配合物的X射线晶体学数据。使用SambVca 2.0程序计算了手性NHC配体的形貌空间位阻。试图获得不稳定的（R a，R a，S，S）-[（DiPh-2-SICyoctNap）Ir（BB）] [PF 6 ]配合物的单晶时，该分解物具有意外的钳型获得了NHC *-二烯配体。分离或新鲜制备了一系列手性阳离子NHC-铱络合物，并将其用于N的代表性对映选择性分子内氢胺化反应-苄基-2
• Developing NHC-Iridium Catalysts for the Highly Efficient Enantioselective Intramolecular Hydroamination Reaction
  作者：Pengchao Gao、Gellért Sipos、Daven Foster、Reto Dorta

  DOI：10.1021/acscatal.7b02508

  日期：2017.9.1

  introduced as catalysts for the intramolecular hydroamination reaction of unactivated aminoalkenes. The catalysts show high activity in the construction of pyrrolidines, which are accessed with excellent optical purity. Enantiomerically enriched piperidines and indolines are also produced, and various functional groups are tolerated with this LTM system. A reaction mechanism is proposed, and a major

  引入手性阳离子NHC-铱络合物作为未活化氨基烯烃的分子内加氢胺化反应的催化剂。所述催化剂在吡咯烷的构造中显示出高活性，其以优异的光学纯度被获得。还生产了对映体富集的哌啶和二氢吲哚，该LTM系统可耐受各种官能团。提出了一种反应机理，并提出和讨论了这些催化剂的主要失活途径。
• 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.
• Tunable chiral monophosphines as ligands in enantioselective rhodium-catalyzed ring-opening of oxabenzonorbornadienes with amines
  作者：Renshi Luo、Ling Xie、Jianhua Liao、Hu Xin、Albert S.C. Chan

  DOI：10.1016/j.tetasy.2014.03.017

  日期：2014.5

  A new tunable chiral monophosphine was used as a ligand for asymmetric rhodium-catalyzed ring-opening of oxabenzonorbornadiene with amines, providing a series of chiral ring-opened products in high yields (up to 97%) and with high enantioselectivities (>99%).The reaction can be performed at rt to obtain the desired product with high enantioselectivity. (C) 2014 Elsevier Ltd. All rights reserved.