(S)-1-(1-methylprop-2-enyl)naphthalene | 56796-86-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-1-(1-methylprop-2-enyl)naphthalene
• 英文别名: (S)-3-(1-naphthyl)-1-butene；(-)-1-((S)-but-3-en-2-yl)naphthalene；(S)-1-(but-3-en-2-yl)naphthalene；(-)-(S)-1-(But-3-en-2-yl)naphthalene；1-[(2S)-but-3-en-2-yl]naphthalene
• CAS: 56796-86-2
• 化学式: C₁₄H₁₄
• 分子量: 182.265
• InChiKey: FPPAXQRBHIIHGV-NSHDSACASA-N

物化性质

• 沸点：
  280.5±10.0 °C(Predicted)
• 密度：
  0.984±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  (S)-4-(1-methylprop-2-enyl)-1,2-dihydronaphthalene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 生成 (S)-1-(1-methylprop-2-enyl)naphthalene
  参考文献：
  名称：

  Hydrovinylation of 1,3-Dienes:  A New Protocol, an Asymmetric Variation, and a Potential Solution to the Exocyclic Side Chain Stereochemistry Problem

  摘要：

  Cyclic and acyclic 1,3-dienes undergo efficient (substrate/catalyst = 72) heterodimerization with ethylene in the presence of a Ni catalyst prepared from [o-(PhCH2O)]C6H4PPh2, [(allyl)2NiBr]2, and Na+ BAr4- (Ar = 3,5-bis-trifluromethylphenyl), giving 1,2-addition products. Yields up to 99% can be realized for several 1-vinylcycloalkenes and 1-substituted 1,3-butadienes. Phospholanes with suitably placed hemilabile ligating groups and phosphoramidites derived from binaphthol are excellent ligands for an asymmetric variation of this reaction, the latter giving 99% yield and >95% ee's for selected substrates. An example of how an exocyclic chiral center can be used to install other stereo-centers in the ring (e. g., the carbon to which the side chain is attached) is also provided. These discoveries open an expeditious entry into several biologically relevant classes of compounds, especially those carrying tetrahydronaphthalene and related heterocyclic moieties.

  DOI：

  10.1021/ja0561338

文献信息

• Bidentate Hydroxyalkyl NHC Ligands for the Copper-Catalyzed Asymmetric Allylic Substitution of Allyl Phosphates with Grignard Reagents
  作者：Magaly Magrez、Yann Le Guen、Olivier Baslé、Christophe Crévisy、Marc Mauduit

  DOI：10.1002/chem.201203969

  日期：2013.1.21

  Demonstrating their potential: Bidentate alkoxy NHC ligands have been used in the copper‐catalyzed asymmetric allylic alkylation of allyl phosphates with Grignard reagents (see scheme). The method provides access to tertiary and quaternary chiral centers with high regio‐ and enantioselectivity. The system is also applied to the synthesis of chiral E,E‐dienes, a key structural motif prevalent in natural

  证明其潜力：用格氏试剂在铜催化的烯丙基磷酸的不对称烯丙基烷基化反应中使用了确定的烷氧基NHC配体（参见方案）。该方法可进入具有高区域和对映选择性的三级和四级手性中心。该系统还适用于手性E，E-二烯的合成，手性E，E-二烯是天然产物中普遍存在的关键结构基序。
• Chelating Hydroxyalkyl NHC as Efficient Chiral Ligands for Room-Temperature Copper-Catalyzed Asymmetric Allylic Alkylation
  作者：Christophe Crévisy、Marc Mauduit、Thomas Jennequin、Joanna Wencel-Delord、Diane Rix、Julien Daubignard

  DOI：10.1055/s-0029-1220127

  日期：2010.7

  The application of chiral chelating hydroxy NHC in copper-catalyzed asymmetric allylic alkylation (Cu-AAA) involving various dialkylzincs and allylic phosphate substrates is reported here. From a library of 11 chiral chelating hydroxyalkyl NHC, a fine-tuning has been done to identify the best architectural features enabling to produce the expected γ-adducts in total regioselectivity, good isolated

  本文报道了手性螯合羟基 NHC 在涉及各种二烷基锌和烯丙基磷酸酯底物的铜催化不对称烯丙基烷基化 (Cu-AAA) 中的应用。从 11 种手性螯合羟烷基 NHC 库中，进行了微调以确定最佳结构特征，从而能够在总区域选择性、良好的分离产率和出色的对映选择性（范围从 93% 到 >98 % ee）。
• Highly enantioselective Cu-catalysed allylic substitutions with Grignard reagents
  作者：Fernando López、Anthoni W. van Zijl、Adriaan J. Minnaard、Ben L. Feringa

  DOI：10.1039/b513887f

  日期：——

  A catalyst system able to perform highly enantioselective Cu-catalysed allylic alkylations with Grignard reagents is described.

  描述了能够利用格氏试剂进行高度对映选择性的Cu催化的烯丙基烷基化的催化剂体系。
• Palladium-Catalyzed Asymmetric Reduction of Racemic Allylic Esters with Formic Acid: Effects of Phosphine Ligands on Isomerization of π-Allylpalladium Intermediates and Enantioselectivity
  作者：Motoi Kawatsura、Yasuhiro Uozumi、Masamichi Ogasawara、Tamio Hayashi

  DOI：10.1016/s0040-4020(99)01107-2

  日期：2000.4

  A new MOP ligand (1b), (R)-(+)-2-(bis(3-trifluoromethylphenyl)phosphino)-2′-methoxy-1,1′-binaphthyl, was found to be more enantioselective than other MOP ligands for the palladium-catalyzed asymmetric reduction of α,α-disubstituted allylic esters with formic acid. The reduction of dl-2-(1-naphthyl)-3-buten-2-yl benzoate gave 3-(1-naphthyl)-1-butene of 90% ee. The higher enantioselectivity of 1b is

  发现一种新的MOP配体（1b）（R）-（+）-2-（双（3-三氟甲基苯基）膦基）-2'-甲氧基-1,1'-联萘基比其他MOP配体对映选择性更高用甲酸催化钯催化α，α-二取代的烯丙基酯的不对称还原。还原苯甲酸dl-2-（1-萘基）-3-丁烯-2-基酯得到90％ee的3-（1-萘基）-1-丁烯。的对映体选择性高1B是归因于快速顺-反通过氧化加成烯丙基酯与钯（0）物种形成π烯丙基钯中间体的异构化。的速率顺-反异构化是通过在磁化饱和转移测定11 H NMR。
• Palladium-Catalyzed asymmetric reduction of allylic esters with a new chiral monodentate ligand, 8-diphenylphosphino-8′-methoxy-1,1′-binaphthyl
  作者：Kaoru Fuji、Minoru Sakurai、Takayoshi Kinoshita、Takeo Kawabata

  DOI：10.1016/s0040-4039(98)01342-2

  日期：1998.8

  8-diphenylphosphino-8′-methoxy-1,1′-binaphthyl (8-MeO-MOP), was used for palladium-catalyzed reduction of allylic carbonates with formic acid. Various methylcarbonates of 3,3′-disubstituted allylic alcohols were converted to the corresponding optically active 1-olefins with this ligand.

  一种新的手性单齿配体8-二苯基膦基8'-甲氧基-1,1'-联萘基（8-MeO-MOP）用于钯催化甲酸还原烯丙基碳酸酯。3，3'-二取代的烯丙基醇的各种碳酸甲酯通过该配体转化为相应的旋光性1-烯烃。