1-(1-苯基乙烯基)-萘 | 28358-65-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-(1-苯基乙烯基)-萘
• 英文名称: 1-(1-naphthyl)styrene
• 英文别名: 1-(1-phenylvinyl)naphthalene；1-(1-phenylethenyl)naphthalene；1-(1-naphthyl)-1-phenylethene；1-Phenyl-1--aethylen
• CAS: 28358-65-8
• 化学式: C₁₈H₁₄
• 分子量: 230.309
• InChiKey: DMMHJGCQMUODLJ-UHFFFAOYSA-N

物化性质

• 熔点：
  60-61 °C
• 沸点：
  377.5±12.0 °C(Predicted)
• 密度：
  1.066±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2902909090

反应信息

• 作为反应物：
  描述：

  1-(1-苯基乙烯基)-萘 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以84%的产率得到1-(1-phenylethyl)naphthalene
  参考文献：
  名称：

  Enantiodifferentiation of a silane and the analogous hydrocarbon by the dirhodium method—silane⋯dirhodium complex interaction

  摘要：

  Chiral silane 1 was enantiodifferentiated by recording NMR spectra in the presence of the chiral dirhodium corn lex Rh-2((II))[(R)-(+)-MtPA(4)] (Rh*). This is the first report of direct chiral recognition by spectroscopic methods with this class of compounds. A comparison with the carba-analogue 2 shows that 1 is a soft Lewis-base ligand and that the Si-H hydrogen is the binding site, presumably by forming an adduct with a (3c-2e) silicon-hydrogen-rhodium contact (end-on), which exists in equilibrium with the free ligands. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.05.030
• 作为产物：
  描述：

  1-(1-Methoxy-but-3-enyl)-2-phenylethynyl-benzene 在 platinum(II) bromde 作用下， 以 1,4-二氧六环 为溶剂， 反应 45.0h， 以76%的产率得到1-(1-苯基乙烯基)-萘
  参考文献：
  名称：

  PtBr₂-Catalyzed Consecutive Enyne Metathesis−Aromatization of 1-(1-Methoxy-but-3-enyl)-2-(1-alkynyl)benzenes:  Dual Role of the Pt Catalyst

  摘要：

  1,7-Enynes 1, connected through an aromatic ring and bearing a leaving methoxy group at the 4-position, underwent the PtBr2-catalyzed enyne metathesis followed by aromatization in one pot to afford vinyl naphthalenes 3 in good to acceptable yields. The cyclobutene intermediate 11a and another intermediate 2a were isolated, indicating that PtBr2 acts as a dual role catalyst: (1) as a transition metal catalyst, it induces the eryne metathesis to produce 11a starting from 1a, and (2) as a Lewis acid catalyst, it facilitates elimination of MeOH from 2a to give the aromatized product 3a.

  DOI：

  10.1021/jo048273q

文献信息

• Direct synthesis of 1,1-diarylalkenes from alkenyl phosphates via nickel(0)-catalysed Suzuki–Miyaura coupling
  作者：Anders L. Hansen、Jean-Philippe Ebran、Thomas M. Gøgsig、Troels Skrydstrup

  DOI：10.1039/b609064h

  日期：——

  A combination of Ni(COD)(2) and PCy(3) promotes effectively the Suzuki-Miyaura cross coupling of 1-arylalkenyl phosphates with aryl boronic acids with yields attaining 99%.

  Ni（COD）（2）和PCy（3）的组合有效地促进了1-芳基烯基磷酸酯与芳基硼酸的Suzuki-Miyaura交叉偶联，收率达到99％。
• Traceless directing group mediated branched selective alkenylation of unbiased arenes
  作者：Soumitra Agasti、Aniruddha Dey、Debabrata Maiti

  DOI：10.1039/c6cc07032a

  日期：——

  –COOH group assisted branched selective olefination of simple arenes.

  –COOH基团辅助简单芳烃的分支选择性烯基化。

• Synergistic combination of visible-light photo-catalytic electron and energy transfer facilitating multicomponent synthesis of β-functionalized α,α-diarylethylamines
  作者：Yanan Wu、Yipin Zhang、Mingjie Jiang、Xunqing Dong、Hitesh B. Jalani、Guigen Li、Hongjian Lu

  DOI：10.1039/c9cc02465d

  日期：——

  combination of electron and energy transfer processes has been developed. The mild reaction conditions allow the radical–radical cross-coupling phenomenon for the multicomponent synthesis of β-arylsulfonyl(diarylphosphinoyl)-α,α-diarylethyl-amines from readily available arylsulfinic acids (diarylphosphine oxides), 1,1-diarylethylenes and arylazides.

  已经开发出一种具有电子和能量转移过程的可见光光催化协同组合的合成策略。温和的反应条件使自由基-自由基的交叉偶联现象可以由易得的芳基亚磺酸（二芳基膦氧化物），1，1-二芳基乙烯和芳基叠氮化物进行多组分合成β-芳基磺酰基（二芳基膦酰基）-α，α-二芳基乙基胺。
• Cobalt-Catalyzed Asymmetric Hydrogenation of 1,1-Diarylethenes
  作者：Jianhui Chen、Chenhui Chen、Chonglei Ji、Zhan Lu

  DOI：10.1021/acs.orglett.6b00453

  日期：2016.4.1

  Highly enantioselective cobalt-catalyzed hydrogenation of 1,1-diarylethenes was developed by using bench-stable chiral oxazoline iminopyridine–cobalt complexes as precatalysts. A unique o-chloride effect was observed to achieve high enantioselectivity. Easy removal as well as further transformations of the chloro group make this protocol a potentially useful alternative to synthesize various chiral

  通过使用稳定的手性恶唑啉亚氨基吡啶-钴络合物作为前催化剂，开发了对映体选择性高的钴催化的1,1-二芳烃的氢化反应。观察到独特的邻氯化物效应实现了高对映选择性。易于除去以及氯基团的进一步转化使该方案成为合成各种手性1,1-二芳基乙烷的潜在有用替代品。此过程可以在室温下1克大气压的氢气中以克为单位成功进行。
• Aqueous Sodium Hydroxide Promoted Cross-Coupling Reactions of Alkenyltrialkoxysilanes under Ligand-Free Conditions
  作者：Emilio Alacid、Carmen Nájera

  DOI：10.1021/jo702570q

  日期：2008.3.1

  alkenyltrialkoxysilanes with aryl iodides, bromides, and chlorides are performed on water using sodium hydroxide as activator at 120 °C under normal or microwave heating. This process occurs in the presence of Pd(OAc)2 or 4-hydroxyacetophenone oxime-derived palladacycle 1 as precatalysts under ligand-free conditions with low Pd loadings (0.01−1 mol %) and using tetra-n-butylammonium bromide as additive. Different

  链烯基三烷氧基硅烷与芳基碘化物，溴化物和氯化物的无氟交叉偶联反应是在120℃下在正常或微波加热下，使用氢氧化钠作为活化剂的，在水中进行的。这个过程发生在钯的存在下（OAC）2或4-羟基乙酰苯酮肟衍生钯化合物1作为具有低的Pd负载量无配体的条件下的预催化剂（0.01-1摩尔％），并用四Ñ-丁基溴化铵作为添加剂。在这些反应条件下，可以将不同的市售乙烯基烷氧基硅烷与相应的苯乙烯交联，最好的底物是乙烯基三甲氧基硅烷或乙烯基三乙氧基硅烷。通过威尔金森催化的炔烃与三乙氧基硅烷的加氢硅烷化反应制得的烯基三乙氧基硅烷，在中等至高β/α区域选择性的微波辐射下，经芳基和乙烯基卤化物立体定向芳基化，分别得到不对称的对苯二甲酸酯，烯基苯和共轭二烯。这种简单的程序允许通过萃取分离产物中的钯进行三步操作，从钯相中回收钯，其中钯的含量非常低（芳基碘化物为2-27.5 ppm，溴化物为76 ppm）。