(Z)-1-(2-naphthyl)-2-trimethylsilylethene | 168007-00-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-1-(2-naphthyl)-2-trimethylsilylethene
• 英文别名: trimethyl-[(Z)-2-naphthalen-2-ylethenyl]silane
• CAS: 168007-00-9
• 化学式: C₁₅H₁₈Si
• 分子量: 226.393
• InChiKey: AAZTYVWKVIOGRA-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  16
• 可旋转键数：
  2
• 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：

  (Z)-1-(2-naphthyl)-2-trimethylsilylethene 在 N-碘代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 以86%的产率得到(Z)-2-(2-iodovinyl)naphthalene
  参考文献：
  名称：

  Synthesis of the racemic forms of carbon–carbon double bond locked analogues of strobilurins which are characterized by a 2-arylcyclopropane ring cis-substituted at C-1 by the methyl (E)-3-methoxypropenoate unit

  摘要：

  The racemic forms of three new carbon-carbon double bond locked analogues of strobilurins, which are characterized by a 2-arylcyclopropane ring cis-substituted at C-1 by the methyl (E)-3-methoxypropenoate unit, have been synthesized according to a strategy which involves the palladiuin-catalyzed synthesis of methyl (E)-3-methoxy-2-[(Z)-2-(aryl)ethenyl]propenoates and their stereospecific cyclopropanation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00334-4
• 作为产物：
  描述：

  trimethyl(2-(naphthalen-2-yl)ethynyl)silane 在 1-甲基吡咯烷 、 二异丁基氢化铝 、 水 、 Rochelle's salt 作用下， 以 正己烷 为溶剂， 反应 70.0h， 以79%的产率得到(Z)-1-(2-naphthyl)-2-trimethylsilylethene
  参考文献：
  名称：

  Synthesis of the racemic forms of carbon–carbon double bond locked analogues of strobilurins which are characterized by a 2-arylcyclopropane ring cis-substituted at C-1 by the methyl (E)-3-methoxypropenoate unit

  摘要：

  The racemic forms of three new carbon-carbon double bond locked analogues of strobilurins, which are characterized by a 2-arylcyclopropane ring cis-substituted at C-1 by the methyl (E)-3-methoxypropenoate unit, have been synthesized according to a strategy which involves the palladiuin-catalyzed synthesis of methyl (E)-3-methoxy-2-[(Z)-2-(aryl)ethenyl]propenoates and their stereospecific cyclopropanation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00334-4

文献信息

• Acid-catalyzed reactions of (3-(naphthalen-2-yl)-2,2-bis(trimethylsilyl)oxiran. A new synthesis of functional-group-substituted vinylsilanes
  作者：Kazem D. Safa、Farnaz Behmagham、Khatereh Ghorbanpour

  DOI：10.1016/j.jorganchem.2011.02.024

  日期：2011.5

  The magnesium bromide-diethyl etherate-catalyzed ring-opening of (3-(naphthalen-2-yl)-2,2-bis(trimethylsilyl)oxiran 2 with thiophenols affords (1-trimethylsilylvinyl)sulfides 3 and the (1-bromovinyl)silane 4. Nucleophilic attack occurs regioselectively at the position α- to silicon. The compound 2 has been converted into the (1-trimethylsilylvinyl)amide 5 with an excess of acetonitrile and into the

  溴化镁-二乙基醚化物催化的（3-（萘-2-基）-2,2-双（三甲基硅烷基）环氧乙烷2与硫酚的开环反应）提供（1-三甲基硅烷基乙烯基）硫化物3和（1-溴乙烯基）硅烷4.亲核性攻击发生在区域α-上，对硅区域选择性地发生，化合物2已与过量的乙腈转化为（1-三甲基硅烷基乙烯基）酰胺5，并与乙酸/乙酸转化为乙酸（1-三甲基硅烷基乙烯基）乙酸酯6。酸酐：这些反应在催化量的三氟化硼-乙醚中进行，仅用乙酸处理2即可得到萘甲醛，环氧化物2也与MgBr 2 OEt 2，MeLi / CuI，HX（X Br或Cl）和LiAlH 4发生反应，并在双（三甲基甲硅烷基）取代的碳上发生亲核攻击。
• Highly Enantioselective Epoxidation of<i>cis</i>-Alkenylsilanes
  作者：Kazuhiro Matsumoto、Takuya Kubo、Tsutomu Katsuki

  DOI：10.1002/chem.200901048

  日期：2009.7.6

  A general and highly enantioselective method for the epoxidation of cis‐alkenylsilanes, in which the epoxysilanes were obtained with complete enantioselectivity in the presence of 0.5–2 mol % of a Ti–Salalen complex. The combination of this epoxidation method and the following transformations is a powerful approach that provides synthetically important epoxides, such as styrene oxides and geminally

  顺式-烯基硅烷环氧化的一种通用且高度对映选择性的方法，其中在0.5–2 mol％的Ti–Salalen配合物存在下，具有完全对映选择性的环氧硅烷被获得。该环氧化方法与以下转化的结合是一种强大的方法，可以提供对映纯形式的合成上重要的环氧化物，例如氧化苯乙烯和双晶双取代的环氧化物。
• IPy2BF4 is also a useful reagent for stereospecific iodine-silicon exchange in open chain trimethylsilylalkenes
  作者：José Barluenga、Lorenzo J. Alvarez-García、JoséM. González

  DOI：10.1016/0040-4039(95)00199-m

  日期：1995.3

  Reaction of the title monosubstituted vinylsilanes with IPy(2)BF(4)/HBF4 gives iodoalkenes through the ipso-substitution process with stereospecific retention of configuration.
• Barluenga Jose, Alvarez-Garcia Lorenzo J., Gonzalez Jose M., Tetrahedron Lett., 36 (1995) N 12, S 2153-2156
  作者：Barluenga Jose, Alvarez-Garcia Lorenzo J., Gonzalez Jose M.

  DOI：——

  日期：——