(1-bromo-2-naphthylmethyl)triphenylphosphonium bromide | 61130-14-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1-bromo-2-naphthylmethyl)triphenylphosphonium bromide
• 英文别名: [(1-Bromonaphthalen-2-yl)methyl](triphenyl)phosphanium bromide；(1-bromonaphthalen-2-yl)methyl-triphenylphosphanium;bromide
• CAS: 61130-14-1
• 化学式: Br*C₂₉H₂₃BrP
• 分子量: 562.283
• InChiKey: ZWIAXAOXDPLCOU-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1-bromo-2-naphthylmethyl)triphenylphosphonium bromide 在 sodium amide 作用下， 以 苯 为溶剂， 生成 (1-bromo-2-naphthylidene)triphenylphosphorane
  参考文献：
  名称：

  Gupta, K. C.; Saxena, B. K.; Pathak, P. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 312 - 314

  摘要：

  DOI：
• 作为产物：
  描述：

  1-溴-2-甲基萘 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 xylene 为溶剂， 生成 (1-bromo-2-naphthylmethyl)triphenylphosphonium bromide
  参考文献：
  名称：

  1,4-二芳基丁烯炔的合成及光谱性质

  摘要：

  已经合成了几种新的二芳基丁烯炔，并描述了nmr和uv光谱的分析。对于平面反式异构体，发现构型偏爱于1-（α-萘基）-，而不是1-（β-萘基）-4-芳基丁烯。在C-1连接到较大芳基的α-或β-位置的化合物之间也发现了这种差异。

  DOI：

  10.1039/p29760001104

文献信息

• Dinaphthopentalenes: Pentalene Derivatives for Organic Thin-Film Transistors
  作者：Takeshi Kawase、Takeru Fujiwara、Chitoshi Kitamura、Akihito Konishi、Yasukazu Hirao、Kouzou Matsumoto、Hiroyuki Kurata、Takashi Kubo、Shoji Shinamura、Hiroki Mori、Eigo Miyazaki、Kazuo Takimiya

  DOI：10.1002/anie.201003609

  日期：2010.10.11

  Extended π system: A nickel(0)‐mediated reaction afforded dinaphthopentalene derivatives, whose electronic and electrochemical properties depend on the fusion patterns. Very high hole mobility was observed for an amorphous material, and the compounds are applicable to organic heterojunction photovoltaic cells (see picture).

  扩展π系统：镍（0）介导的反应提供了二萘并戊二烯衍生物，其电子和电化学性质取决于融合模式。对于非晶材料，观察到非常高的空穴迁移率，并且这些化合物适用于有机异质结光伏电池（参见图片）。
• Synthesis of Helicenes Utilizing Palladium-Catalyzed Double C−H Arylation Reaction
  作者：Ken Kamikawa、Ippei Takemoto、Shin Takemoto、Hiroyuki Matsuzaka

  DOI：10.1021/jo0711586

  日期：2007.9.1

  [5]- and [6]helicenes were synthesized in moderate to good yields from Z,Z-bis(bromostilbene)s by palladium-catalyzed double C−H arylation reaction. This method can be applied to the syntheses of helicenes possessing electron-deficient substituents.

  [5]-和[6]螺旋烯是通过钯催化的双CH芳基化反应从Z，Z-双（溴化苯乙烯）合成的，产率中等至良好。该方法可以应用于具有电子不足的取代基的螺旋烯的合成。
• Construction of Indoline/Indolenine Ring Systems by a Palladium-Catalyzed Intramolecular Dearomative Heck Reaction and the Subsequent Aza-semipinacol Rearrangement
  作者：Dong Gao、Lei Jiao

  DOI：10.1021/acs.joc.1c00209

  日期：2021.4.16

  The palladium-catalyzed intramolecular dearomative Heck reaction of 2,3-disubstituted indoles serves as an access to spiro-indoline products. Herein, we report an efficient construction of indoline/indolenine core stuctures via a dearomative Heck reaction of simple 2,3-disubstituted indoles with all-carbon tethers and the subsequent aza-semipinacol rearrangement. The Heck reaction features a high C2-selectivity

  2,3-二取代的吲哚的钯催化的分子内脱芳香性Heck反应可作为螺二氢吲哚产物的途径。在这里，我们报告了通过简单的2，3-二取代的吲哚与全碳系链的脱芳香性Heck反应以及随后的氮杂-semipinacol重排，有效构建吲哚啉/吲哚烯核心结构的方法。Heck反应具有高的C 2-选择性，并且已经通过DFT计算研究了立体有择的芳基/烷基迁移选择性。使用这种方法，我们完成了akuammiline生物碱长春花碱的正式全合成。
• Palladium(0)-Catalyzed Arylative Dearomatization of Phenols
  作者：Sophie Rousseaux、Jorge García-Fortanet、Miguel Angel Del Aguila Sanchez、Stephen L. Buchwald

  DOI：10.1021/ja203644q

  日期：2011.6.22

  The palladium-catalyzed arylative dearomatization of phenols to yield spirocyclohexadienone products in good to excellent yields has been developed. Preliminary results demonstrate that the formation of the spirocyclic all-carbon quaternary center can be accomplished with high levels of enantiocontrol (up to 91% ee).
• Synthesis of Bicyclic Dioxetanes Bearing a Hydroxyphenanthrene or Hydroxy[4]helicene Moiety and Their Base-Induced Chemiluminescent Decomposition
  作者：Masakatsu Matsumoto、Yohei Koyama、Nobuko Watanabe、Hisako K. Ijuin

  DOI：10.3987/com-14-s(k)43

  日期：——

  Six bicyclic dioxetanes bearing a 1-hydroxyphenanthren-3-yl 2-iv, 3-hydroxyphenanthren-1-yl 2-ov, 4-hydroxyphenanthren-2-yl 2-oh, 2-hydroxyphenanthren-4-yl 2-ih, 4-hydroxy[4]helicen-2-yl 3-iv and 2-hydroxy[4]helicen-4-yl group 3-ov were synthesized and their base-induced chemiluminescent decomposition was investigated in a TBAF (tetrabutylammonium fluoride) / MeCN system. For dioxetanes in the iv-series 2-iv and 3-iv including alpha-naphthol-analog 17a and those in the ov-series 2-ov and 3-ov including beta-naphthol-analog 17b, we investigated how the chemiluminescence properties changed with an increase in the number of fused benzene rings of a hydroxyarene moiety attached to a dioxetane ring. The results showed that a) maximum wavelength of chemiluminescence lambda(CL)(max) tended to shift to a longer wavelength region as the number of fused benzene rings increased, b) the k(CTID) values for the iv-series were >1000 times larger than those for the ov-series regardless of the number of fused benzene rings, and c) a dioxetane in the iv-series tended to have a higher singlet-chemiexcitation efficiency Phi(S) than the corresponding dioxetane in the ov-series. This tendency could be explained by the "syn/anti" rotational isomerism of an aromatic electron donor, where an anti-rotamer gives Phi(S) far more effectively than a syn-rotamer.