1-(pent-1-enyl)naphthalene | 3099-63-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(pent-1-enyl)naphthalene
• 英文别名: 1-(1-Naphthyl)-penten-(1)；1-Pent-1-enylnaphthalene
• CAS: 3099-63-6
• 化学式: C₁₅H₁₆
• 分子量: 196.292
• InChiKey: AGZOIXITJLBHAX-UHFFFAOYSA-N

物化性质

• 沸点：
  322.3±9.0 °C(predicted)
• 密度：
  0.993±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  1-(pent-1-enyl)naphthalene 在 N-溴代丁二酰亚胺(NBS) 、 水 、 diethylzinc 、 三氟乙酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 4.0h， 生成 2-(naphthalen-1-yl)pentanal
  参考文献：
  名称：

  CF 3 CO 2 ZnEt介导的溴代醇的高度区域选择性重排为醛

  摘要：

  描述了由CF 3 CO 2 ZnEt介导的溴代醇对醛类的高效选择性重排反应。仲醛和叔醛是在温和的条件下以良好至极佳的收率（85–99％）制备的。还研究了这种重排过程的范围和局限性。

  DOI：

  10.1016/j.tetlet.2011.08.134
• 作为产物：
  描述：

  1-(1-naphthyl)-1-pentanol 在 氯化亚砜 、 sodium t-butanolate 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 12.03h， 生成 4-(4-n-pentylnaphthalen-1-yl)morpholine 、 1-(pent-1-enyl)naphthalene
  参考文献：
  名称：

  Palladium-Catalyzed Amination of Chloromethylnaphthalene and Chloromethylanthracene Derivatives with Various Amines

  摘要：

  Palladium-catalyzed amination of chloromethylnaphthalene and chloromethylanthracene derivatives to produce naphthylamines and anthrylamines in satisfactory to good yields has been developed. The unprecedented amination reactions proceeded smoothly under mild conditions in the presence of Pd(PPh3)(4) as a catalyst.

  DOI：

  10.1021/ja300164d

文献信息

• FeCl₂-catalyzed hydroboration of aryl alkenes with bis(pinacolato)diboron
  作者：Yang Liu、Yuhan Zhou、Huan Wang、Jingping Qu

  DOI：10.1039/c5ra14869c

  日期：——

  Alkylboronates were synthesized by a ligand-free ferrous chloride catalyzed anti-Markovnikov hydroboration of un-activated aryl alkenes with bis(pinacolato)diboron.

  烷基硼酸酯是通过无配体的氯化亚铁催化的非马尔科夫尼科夫氢硼化反应合成的，该反应使用双(邻苯二甲醇)二硼烷对未活化的芳基烯烃进行反应。
• 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。
• Copper-Free Asymmetric Allylic Alkylation with Grignard Reagents
  作者：Olivier Jackowski、Alexandre Alexakis

  DOI：10.1002/anie.201000577

  日期：2010.4.26

  Open wide and say AAA: The copper‐free asymmetric allylic alkylation reaction of Grignard reagents, catalyzed by N‐heterocyclic carbenes, is reported for allyl bromide derivatives. This reaction offers good enantioselectivity and good to excellent γ regioselectivity, particularly for the formation of quaternary chiral centers (see scheme; Mes=mesityl).

  张开嘴说AAA：据报道，N-杂环卡宾催化了格氏试剂的无铜不对称烯丙基烷基化反应，是烯丙基溴衍生物的反应。该反应提供了良好的对映选择性和良好的至优异的γ区域选择性，特别是对于形成四元手性中心（参见方案； Mes ＝甲磺酰基）。
• CF3CO2ZnEt-mediated highly regioselective rearrangement of bromohydrins to aldehydes
  作者：Zhihui Wang、Meiyi Li、Wenqin Zhang、Jiangnan Jia、Fei Wang、Song Xue

  DOI：10.1016/j.tetlet.2011.08.134

  日期：2011.11

  A highly efficient and selective rearrangement reaction of bromohydrins to aldehydes mediated by CF3CO2ZnEt was described. The secondary and tertiary aldehydes were prepared under mild conditions in good to excellent yields (85–99%). The scope and limitations of this rearrangement process were also investigated.

  描述了由CF 3 CO 2 ZnEt介导的溴代醇对醛类的高效选择性重排反应。仲醛和叔醛是在温和的条件下以良好至极佳的收率（85–99％）制备的。还研究了这种重排过程的范围和局限性。
• Palladium-Catalyzed Amination of Chloromethylnaphthalene and Chloromethylanthracene Derivatives with Various Amines
  作者：Sheng Zhang、Yi Wang、Xiujuan Feng、Ming Bao

  DOI：10.1021/ja300164d

  日期：2012.3.28

  Palladium-catalyzed amination of chloromethylnaphthalene and chloromethylanthracene derivatives to produce naphthylamines and anthrylamines in satisfactory to good yields has been developed. The unprecedented amination reactions proceeded smoothly under mild conditions in the presence of Pd(PPh3)(4) as a catalyst.