(S)-4-(1-methylprop-2-enyl)-1,2-dihydronaphthalene | 874919-15-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-4-(1-methylprop-2-enyl)-1,2-dihydronaphthalene
• 英文别名: 4-[(2S)-but-3-en-2-yl]-1,2-dihydronaphthalene
• CAS: 874919-15-0
• 化学式: C₁₄H₁₆
• 分子量: 184.281
• InChiKey: WANXOSSAVXKJJM-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (S)-4-(1-methylprop-2-enyl)-1,2-dihydronaphthalene 在 9-borabicyclo[3.3.1]nonane dimer 、 Crabtree's catalyst 、 氢气 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 65.5h， 生成 (3S)-3-(1,2,3,4-tetrahydronaphthalen-1-yl)butan-1-ol
  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
• 作为产物：
  描述：

  3,4-dihydro-1-vinylnaphthalene 、 乙烯 在 bi(allylnickel bromide) 、 chiral phosphoramidite ligand 、 Na{[1,3-(CF₃)2C₆H₃]4B} 作用下， 以 二氯甲烷 为溶剂， -55.0 ℃ 、101.32 kPa 条件下， 反应 5.0h， 生成 (S)-4-(1-methylprop-2-enyl)-1,2-dihydronaphthalene
  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

• Hydrovinylation of 1,3-Dienes:  A New Protocol, an Asymmetric Variation, and a Potential Solution to the Exocyclic Side Chain Stereochemistry Problem
  作者：Aibin Zhang、T. V. RajanBabu

  DOI：10.1021/ja0561338

  日期：2006.1.1

  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.