(R)-2,3-dihydro-2-(naphthalen-2-yl)furan | 131516-09-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-2,3-dihydro-2-(naphthalen-2-yl)furan
• 英文别名: 2-(2-naphthyl)-2,3-dihydrofuran；(R)-2-(2-naphthyl)-2,3-dihydrofuran；(R)-2-(Naphthalen-2-yl)-2,3-dihydrofuran；(2R)-2-naphthalen-2-yl-2,3-dihydrofuran
• CAS: 131516-09-1
• 化学式: C₁₄H₁₂O
• 分子量: 196.249
• InChiKey: UKPUMDLVNAKFTB-CQSZACIVSA-N

物化性质

• 沸点：
  339.9±42.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-2,3-dihydro-2-(naphthalen-2-yl)furan 在 lithium aluminium tetrahydride 、 四氯化钛 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 N-[(R)-1-((2S,3R,5R)-2-Cyano-5-naphthalen-2-yl-tetrahydro-furan-3-yl)-2-hydroxy-ethyl]-4-methyl-benzenesulfonamide
  参考文献：
  名称：

  TiCl₄-Promoted Multicomponent Reaction:  A New Entry to Functionalized α-Amino Acids

  摘要：

  TiCl4-promoted multicomponent reactions involving N-tosyl imino ester, cyclic enol ether, and silane reagents in a single one-pot operation provide functionalized alpha-amino acids with multiple stereogenic centers in good to excellent yields. Cis/trans selectivities with optically active substituted dihydrofurans have been investigated.

  DOI：

  10.1021/ol048302j
• 作为产物：
  描述：

  2,3-二氢呋喃 、 2-萘基三氟甲烷磺酸 在 C₁₈H₂₈Cl₂N₂NiP₂ 、 锌 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以67%的产率得到(R)-2,3-dihydro-2-(naphthalen-2-yl)furan
  参考文献：
  名称：

  镍催化的芳基三氟甲磺酸酯，甲磺酸酯和甲苯磺酸酯的对映选择性分子间Heck和还原Heck反应

  摘要：

  镍催化的环烯烃的分子间Heck反应与芳基三氟甲磺酸酯，甲磺酸酯和甲苯磺酸酯的对映体比率极好。不对称的还原性Heck反应也适用于2-环戊烯酮缩酮，这相当于烯酮本身的共轭芳基化。

  DOI：

  10.1002/anie.202011036

文献信息

• Rational design of cyclopropane-based chiral PHOX ligands for intermolecular asymmetric Heck reaction
  作者：Marina Rubina、William M Sherrill、Alexey Yu Barkov、Michael Rubin

  DOI：10.3762/bjoc.10.158

  日期：——

  rigid cyclopropyl backbone was synthesized and tested in the intermolecular asymmetric Heck reaction. Mechanistic modelling and crystallographic studies were used to predict the optimal ligand structure and helped to design a very efficient and highly selective catalytic system. Employment of the optimized ligands in the asymmetric arylation of cyclic olefins allowed for achieving high enantioselectivities

  合成了一类新的具有构象刚性环丙基骨架的手性磷酰基-恶唑啉 (PHOX) 配体，并在分子间不对称 Heck 反应中进行了测试。机械建模和晶体学研究用于预测最佳配体结构，并有助于设计非常有效和高选择性的催化系统。在环烯烃的不对称芳基化中使用优化的配体可以实现高对映选择性并显着抑制产物异构化。确定了影响选择性和异构化速率的因素。表明这种异构化的性质不同于先前使用手性二膦配体所证明的性质。
• The Regioselectivity of the Asymmetric Intermolecular Heck Reaction with Planar Chiral Diphosphine–Oxazoline Ferrocenyl Ligands
  作者：Tao Tu、Wei-Ping Deng、Xue-Long Hou、Li-Xin Dai、Xi-Cheng Dong

  DOI：10.1002/chem.200204450

  日期：2003.7.7

  chiral diphosphine-oxazoline ferrocenyl ligands were synthesized and used efficiently in the palladium-catalyzed asymmetric intermolecular Heck reaction of 2,3-dihydrofuran with aryl triflate and cyclohexenyl triflate. The tuning of the regioselectivity was realized by means of different palladium precursors and by changing the electronic factor of the ligands. A plausible rationale based on the existed

  合成了一系列新型平面手性二膦-恶唑啉二茂铁配体，并有效地用于钯催化的 2,3-二氢呋喃与三氟甲磺酸芳基酯和三氟甲磺酸环己烯酯的不对称分子间 Heck 反应。区域选择性的调节是通过不同的钯前体和改变配体的电子因子来实现的。提供了基于现有机制的合理理由。
• Palladium-catalyzed asymmetric arylation of 2,3-dihydrofuran: 1,8-Bis(dimethylamino)naphthalene as an efficient base
  作者：Fumiyuki Ozawa、Akihiko Kubo、Tamio Hayashi

  DOI：10.1016/s0040-4039(00)91654-x

  日期：1992.3

  Reaction of 2,3-dihydrofuran with aryl triflate (1) in the presence of a base and a palladium catalyst, generated in situ from Pd(OAc)2 and (R)-BINAP, gave (R)-2-aryl-2,3-dihydrofuran (2) and a small amount of (S)-2-aryl-2,5-dihydrofuran (3). The enantiomeric purity of major product 2 was strongly affected by the base. 1,8-Bis(dimethylamino)naphthalene (proton sponge) as a highly basic and sterically

  在碱和钯催化剂存在下，由Pd（OAc）2和（R）-BINAP原位产生的2,3-二氢呋喃与三氟甲磺酸芳基酯（1）反应，得到（R）-2-芳基-2 ，3-二氢呋喃（2）和少量的（S）-2-芳基-2,5-二氢呋喃（3）。碱强烈影响主要产物2的对映体纯度。1,8-双（二​​甲基氨基）萘（质子海绵）是一种高度碱性且对空间有要求的胺，对于各种芳基三氟甲磺酸酯，其（R）-2的对映选择性高（> 96-87％ee）。
• Kinetic resolution of 2-substituted-2,3-dihydrofurans by a palladium-catalyzed asymmetric Heck reaction
  作者：Hao Li、Shi-Li Wan、Chang-Hua Ding、Bin Xu、Xue-Long Hou

  DOI：10.1039/c5ra17374d

  日期：——

  The kinetic resolution of 2-substituted-dihydrofurans via a Pd-catalyzed asymmetric Heck reaction was realized for the first time.

  通过Pd催化的不对称Heck反应，首次实现了对2-取代二氢呋喃的动力学分辨。
• Exploiting the<i>gem</i>-Disubstitution Effect in FcPHOX and HetPHOX P,N Ligands: Synthesis and Applications in Pd-Catalyzed Intermolecular Heck Reactions
  作者：Dennis McCartney、Chris Nottingham、Helge Müller-Bunz、Patrick J. Guiry

  DOI：10.1021/acs.joc.5b01764

  日期：2015.10.16

  The synthesis of a range of novel gem-disubstituted and electronically varied thiophene-oxazoline (HetPHOX) ligands and ferrocene-oxazoline (FcPHOX) ligands and their application in the Pd-catalyzed intermolecular asymmetric Heck reaction (IAH) is described. These investigations show that gem-disubstitution of i-Pr-PHOX-type ligands can lead to effective and cost-efficient alternatives to the corresponding t-Bu-PHOX systems. The Pd complexes of these ligands were very effective in the IAH, providing phenylated products in up to 100% conversion with up to 97% ee.