2,3-Dihydro-4-phenyl-1H-benzindene | 13225-63-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 2,3-Dihydro-4-phenyl-1H-benzindene
• 英文别名: 4-phenyl-2,3-dihydro-1H-cyclopenta[b]naphthalene；4-phenyl-2,3-dihydro-1H-cyclopenta[b]naphtalene；4-Phenyl-2,3-dihydro-14-benzinden
• CAS: 13225-63-3
• 化学式: C₁₉H₁₆
• 分子量: 244.336
• InChiKey: LZKTWCOKXVUUCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  phenyl 2-(trimethylsilylethynyl)phenyl ketone 在 tungsten pentacarbonyl tetrahydrofuran 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 29.0h， 生成 2,3-Dihydro-4-phenyl-1H-benzindene
  参考文献：
  名称：

  五羰基苯并吡喃基钨(0)配合物的新合成及其与富电子烯烃的Diels-Alder反应

  摘要：

  DOI：

  10.1021/ja001481p

文献信息

• Phthalazines. XV. Ring transformation of phthalazines into naphthalenes by means of inverse-electron-demand Diels-Alder reaction.
  作者：Etsuo OISHI、Naokata TAIDO、Ken-ichi IWAMOTO、Akira MIYASHITA、Takeo HIGASHINO

  DOI：10.1248/cpb.38.3268

  日期：——

  The 1-substituted phthalazines 6 underwent inverse-electron-demand Diels-Alder reaction with the enamines 3 and ynamines 9, resulting in the formation of 1-substituted naphthalenes.Thus, 1-phthalazinecarbonitrile (6b) reacted with 3a-i to give the corresponding 1-naphthonitriles 7a-e, g, h and 2, 3-kihydro-1-naphthonitriles 8f, i, respectively. Similarly, reaction of 1-(methylsulfonyl)phthalazine (6c) with 3a, b, d, f gave the corresponding 1-(methylsulfonyl)naphthalenes 10a, b, d and 1-(methylsulfonyl)-2, 3-dihydronaphthalene 11f. Furthermore, 1-methylthio- (6e), 1-phenyl- (6f), 1-methyl-(6b), 1-chlorophthalazines (6h) and phthalazine (6a) reacted with 3a to afford the corresponding 4-substituted 2, 3-dihydro-1H-benz[f]indenes 12e-h, a, respectively.A similar ring transformation was found to proceed between 1, 4-phthalazinedicarbonitrile (14) and 1-methyl-1H-indole (13), giving the benzo[b]carbazoledicarbonitrile (15).Compounds 6b and 6c also underwent inverse-electron-demand Diels-Alder reaction with the ynamines 9a, b to give the corresponding 1-cyano-16a, b and 1-(methylsulfonyl)naphthalenes 17a, b, respectively.

  因此，1-酞嗪甲腈（6b）与 3a-i 反应，分别得到相应的 1-萘甲腈 7a-e、g、h 和 2、3-基氢-1-萘甲腈 8f、i。同样，1-（甲磺酰基）酞嗪（6c）与 3a、b、d、f 反应，得到相应的 1-（甲磺酰基）萘 10a、b、d 和 1-（甲磺酰基）-2，3-二氢萘 11f。此外，1-甲硫基（6e）、1-苯基（6f）、1-甲基（6b）、1-氯酞嗪（6h）和酞嗪（6a）与 3a 反应，分别得到相应的 4-取代的 2，3-二氢-1H-苯并[f]茚 12e-h、a。化合物 6b 和 6c 还与亚萘胺 9a 和 b 发生了反电子需求的 Diels-Alder 反应，分别得到了相应的 1-氰基-16a、b 和 1-（甲磺酰基）萘 17a、b。
• Thermal and Au(I)-Catalyzed Intramolecular [4+2] Cycloaddition of Aryl-Substituted 1,6-Diynes for the Synthesis of Biaryl Compounds
  作者：Takanori Shibata、Ryo Fujiwara、Daisuke Takano

  DOI：10.1055/s-2005-871959

  日期：——

  1,6-Diynes, possessing aryl groups on their termini, undergo an intramolecular [4+2] cycloaddition via strained cyclic allene intermediates to give various biaryl compounds. Under thermal conditions, isomerization of the intermediates occurs, while, in the presence of a cationic gold catalyst, skeletal rearrangement is a major pathway.

  1,6-二炔在其末端具有芳基，通过紧张的环状丙二烯中间体进行分子内[4+2]环加成，得到各种联芳基化合物。在热条件下，中间体发生异构化，而在阳离子金催化剂的存在下，骨架重排是主要途径。
• Gold-Catalyzed Synthesis of Bicyclo[4.3.0]nonadiene Derivatives via Tandem 6-<i>endo-dig</i>/Nazarov Cyclization of 1,6-Allenynes
  作者：Guan-You Lin、Chun-Yao Yang、Rai-Shung Liu

  DOI：10.1021/jo0707939

  日期：2007.8.31

  Catalytic cyclization of 1,6-allenynes was achieved by AuPPh3SbF6 (5 mol %) in cold CH2Cl2 (0 °C, 0.5−4 h) to form bicyclo[4.3.0]nonadiene products; this cyclization proceeded more efficiently for a substrate bearing R = alkyl (yields >70%). We propose a reaction mechanism involving a 6-endo-dig cyclization of Au(I)-π-alkyne, followed by Nazarov cyclization.

  1，6-炔烃的催化环化反应是通过AuPPh 3 SbF 6（5 mol％）在冷CH 2 Cl 2（0°C，0.5-4 h）中形成双环[4.3.0]壬二烯产物形成的。对于带有R =烷基的底物（收率> 70％），该环化反应更有效地进行。我们提出了一种反应机理，涉及Au（I）-π-炔烃的6-内挖-环化，然后是Nazarov环化。
• Gold-Catalyzed Intramolecular [3 + 2]-Cycloaddition of Arenyne-Yne Functionalities
  作者：Jian-Jou Lian、Po-Chiang Chen、Yau-Ping Lin、Hao-Chun Ting、Rai-Shung Liu

  DOI：10.1021/ja0643826

  日期：2006.9.1

  We report a new efficient intramolecular [3 + 2]-cycloaddition of unactivated arenyne (or enyne)-yne functionalities, catalyzed mainly by the AuPPh3SbF6 complex (2 mol %) under ambient conditions. The value of this cyclization is reflected by its applicability to a wide range of diyne substrates bearing various functional groups.
• Z-selective, anti-Markovnikov addition of alkoxides to terminal alkynes: an electron transfer pathway?
  作者：James Cuthbertson、Jonathan D. Wilden

  DOI：10.1016/j.tet.2015.04.038

  日期：2015.6

  Potassium alkoxides undergo anti-Markovnikov addition to aryl-substituted alkynes with Z selectivity in DMF as the solvent. The yields and efficiency of the reaction was also found to be enhanced by the addition of a secondary amine ligand such as N,N'-dimethylethylenediamine. Mechanistic investigations suggest that the products, reaction rates and selectivity can be explained via a single electron transfer from the alkoxide to the alkyne. This leads to a radical anion intermediate, which then rapidly combines with the alkoxide to yield a vinyl anion whose lifetime governs the E:Z selectivity observed in the products. (C) 2015 The Authors. Published by Elsevier Ltd.