cis-2-(3,3-dimethyl-1-butenyl)naphthalene | 80014-42-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: cis-2-(3,3-dimethyl-1-butenyl)naphthalene
• 英文别名: cis-3,3-dimethyl-1-(2-naphthyl)-1-butene；(Z)-2-(3,3-dimethylbut-1-en-1-yl)naphthalene；2-[(Z)-3,3-dimethylbut-1-enyl]naphthalene
• CAS: 80014-42-2
• 化学式: C₁₆H₁₈
• 分子量: 210.319
• InChiKey: HUVKAKJAEPNATB-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  cis-2-(3,3-dimethyl-1-butenyl)naphthalene 在 2-萘乙酮 作用下， 生成 (E)-2-(3,3-dimethylbut-1-en-1-yl)naphthalene
  参考文献：
  名称：

  氧对 3,3-二甲基-1-(2-萘基)-1-丁烯三联体敏化异构化中光稳态组成的影响

  摘要：

  测定了苯中 3,3-二甲基-1-(2-萘基)-1-丁烯的三重敏化异构化的光稳态组成和量子产率。光稳定状态下反式异构体的比例随着氧气浓度的增加而增加，这与 azulene 效应相结合，表明 transoid 和扭曲的三联体都被氧气淬灭。

  DOI：

  10.1246/cl.1980.1335
• 作为产物：
  描述：

  2-(3,3-dimethylbut-1-yn-1-yl)naphthalene 在 乙醇 、 potassium tert-butylate 、 1,3-双(2,4,6-三甲基苯基)氯化咪唑 、 联硼酸频那醇酯 、 copper(l) chloride 作用下， 反应 5.0h， 以62%的产率得到cis-2-(3,3-dimethyl-1-butenyl)naphthalene
  参考文献：
  名称：

  Diboron-Assisted Copper-Catalyzed Z-Selective Semihydrogenation of Alkynes Using Ethanol as a Hydrogen Donor

  摘要：

  We herein describe a B(2)Pin(2)-assisted copper-catalyzed semihydrogenation of alkynes. A variety of alkenes were obtained in good to excellent yields with Z-selectivity under mild reaction conditions. Mechanistic studies indicated that a transfer hydrogenation process was involved and ethanol acted as both a solvent and a hydrogen donor in this reaction. The present protocol enabled convenient synthesis of deuterium-substituted Z-alkenes such as Z-Combretastain A4-d(2) in a high deuteration ratio by using readily available ethanol-d(1) as the deuterium source.

  DOI：

  10.1021/acs.joc.9b00321

文献信息

• Cu-mediated or metal-free alkylation of gem-dibromoalkenes with tertiary, secondary and primary alkyl Grignard reagents
  作者：Yupian Deng、Xuxue Zhang、Chuan Liu、Song Cao

  DOI：10.1016/j.tet.2020.131804

  日期：2021.2

  A novel copper-mediated or transition-metal-free alkylation of gem-dibromoalkenes with tertiary, secondary and primary alkyl Grignard reagents was described. The outcomes of these reactions were found to be highly dependent on the reaction conditions and the type of Grignard reagents used. Specifically, the tertiary alkylation of gem-dibromoalkenes proceeded efficiently in the presence of 50 mol% CuCN

  描述了用叔，仲和伯烷基格氏试剂对宝石-二溴烯烃进行新型的铜介导或无过渡金属的烷基化。发现这些反应的结果高度依赖于反应条件和所用格氏试剂的类型。具体地说，在50mol％的CuCN存在下或在无过渡金属的条件下，宝石-二溴烯烃的叔烷基化有效地进行，从而以高收率提供了叔烷基取代的单溴烯烃或烯烃。
• Action of Electron-Accepting Quenchers in Photoisomerization of Naphthylethylenes in Polar and Nonpolar Solvents
  作者：Takahisa Oguchi、Tatsuo Arai、Hirochika Sakuragi、Katsumi Tokumaru

  DOI：10.1246/bcsj.60.2395

  日期：1987.7

  The quantum yield of trans-cis isomerization of 3,3-dimethyl-1-(2-naphthyl)-1-butene was measured in the presence of various electron-accepting quenchers in benzene or in acetonitrile. In benzene the quantum yield was increased by addition of some of the quenchers; however, in acetonitrile it was decreased under similar conditions. This was attributed to more efficient formation of olefin triplets through an exciplex in benzene than through radical ion pairs in acetonitrile.

  在苯或乙腈中，测量了 3,3-二甲基-1-(2-萘基)-1-丁烯在各种电子接受淬灭剂存在下的反式-顺式异构化量子产率。在苯中，加入某些淬灭剂后，量子产率会增加；但在乙腈中，在类似条件下，量子产率会降低。这是因为在苯中通过赋形剂形成烯烃三胞胎比在乙腈中通过自由基离子对形成烯烃三胞胎更有效。
• Solvent Dependence of Magnetic Field Effects upon Photoisomerization of 2-(3,3-Dimethyl-1-butenyl)naphthalene in the Presence of Electron Acceptors
  作者：Hirochika Sakuragi、Ryoichi Nakagaki、Kazuhiko Naitoh、Takahisa Oguchi、Tatsuo Arai、Katsumi Tokumaru、Saburo Nagakura

  DOI：10.1246/bcsj.67.86

  日期：1994.1

  The efficiency of isomerization of trans-2-(3,3-dimethyl-1-butenyl)naphthalene (t-BN) in the presence of electron acceptors was reduced by an applied magnetic field in polar solvents such as acetonitrile. This effect together with laser flash photolysis studies indicates that the precursor of isomerization is the BN triplet arising from intersystem crossing of a singlet radical pair consisting of a

  在电子受体存在下，反式-2-(3,3-二甲基-1-丁烯基)萘 (t-BN) 的异构化效率因在极性溶剂（如乙腈）中施加磁场而降低。这种效应与激光闪光光解研究一起表明异构化的前体是由 t-BN 阳离子和受体阴离子组成的单线态自由基对的系统间交叉产生的 BN 三线态。使用外部磁场效应以及激光闪光光解来估计离子自由基对在各种溶剂中对二氰基苯存在下对 t-BN 异构化的贡献。在所用溶剂中，几乎通过氯仿中的激基复合物 (e = 4.8) 最有效地生产 t-BN 三重峰。
• Intermediates for Photoisomerization of a Butenylnaphthalene in the Presence of Electron Acceptors as Studied by Solvent Dependence of Magnetic Field Effects
  作者：Kazuhiko Naitoh、Takahisa Oguchi、Ryoichi Nakagaki、Tatsuo Arai、Hirochika Sakuragi、Katsumi Tokumaru、Saburo Nagakura

  DOI：10.1246/cl.1992.1077

  日期：1992.6

  isomerization of trans-2-(3,3-dimethyl-1-butenyl)naphthalene (t-BN) in the presence of an electron acceptor in various solvents. The precursor of isomerization, t-BN triplet, was produced most efficiently almost through an exciplex in chloroform (e = 4.8) among the employed solvents.

  外部磁场效应以及激光闪光光解被用来估计离子自由基对对反式-2-（3,3-二甲基-1-丁烯基）萘（t-BN）异构化的贡献。各种溶剂中的电子受体。异构化的前体，t-BN 三重态，在所用溶剂中几乎通过在氯仿 (e = 4.8) 中的激基复合物最有效地生产。
• TOKUMARU, KOKKI, GEHNDAJ KAGAKU,(1988) N07, S. 16-23
  作者：TOKUMARU, KOKKI

  DOI：——

  日期：——