(2-methylnaphthalen-1-yl)diphenylphosphane | 540483-74-7

• 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: (2-methylnaphthalen-1-yl)diphenylphosphane
• 英文别名: (2-Methylnaphthalen-1-yl)(diphenyl)phosphane；(2-methylnaphthalen-1-yl)-diphenylphosphane
• CAS: 540483-74-7
• 化学式: C₂₃H₁₉P
• 分子量: 326.378
• InChiKey: IMALWLLOKGKUJG-UHFFFAOYSA-N

物化性质

• 沸点：
  462.0±24.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 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：

  2-溴-2-甲基丙酸乙酯 、 (2-methylnaphthalen-1-yl)diphenylphosphane 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 1-金刚烷甲酸 、 sodium acetate 作用下， 反应 21.0h， 以65%的产率得到
  参考文献：
  名称：

  通过 P-Ru-C 键定向 δ-激活实现萘的远程 C5 选择性功能化

  摘要：

  在萘衍生物的邻位、间位和对位之外进行位点选择性功能化非常具有挑战性，尤其是对于相邻苯环对位的远程 C5 位置。在此，我们报告了萘的远程 C5 选择性功能化叔膦诱导的钌催化的δ键活化。该策略超越了传统的位点选择性，有效地将不同的官能团（烷基、氟烷基和醛）安装在 C5 位置，具有出色的区域选择性（C5/其他 >20:1）。此外，该协议还适用于多环芳烃和更偏远的 C8 位置。初步机理研究表明，叔膦基团在反应中起两个重要作用：第一，它有助于在 C8 位引入 Ru-C 键；其次，由于诱导效应，它通过形成供电子的 P-Ru-C 键来辅助 δ 键的活化。

  DOI：

  10.1021/acscatal.2c00839

文献信息

• Synthesis of <i>peri</i>-Substituted (Naphthalen-1-yl)phosphine Ligands by Rhodium(I)-Catalyzed Phosphine-Directed C–H Arylation
  作者：Xue Luo、Jia Yuan、Chang-Duo Yue、Zi-Yang Zhang、Jian Chen、Guang-Ao Yu、Chi-Ming Che

  DOI：10.1021/acs.orglett.8b00305

  日期：2018.4.6

  A novel protocol for effective rhodium(I)-catalyzed C–H arylation of tertiary phosphines has been devised. It is amenable to a wide range of substrates and gives the products in moderate to high yields. This strategy provides a simple and efficient route to peri-substituted (naphthalen-1-yl)phosphines.

  已经设计出有效的铑（I）催化叔膦的CH芳基化的新协议。它适用于各种基材，并能以中等到高产量提供产品。该策略提供了一种简单而有效的路线周围取代的（萘-1-基）膦。
• Efficient Bulky Phosphines for the Selective Telomerization of 1,3-Butadiene with Methanol
  作者：Mathieu J.-L. Tschan、Eduardo J. García-Suárez、Zoraida Freixa、Hélène Launay、Henk Hagen、Jordi Benet-Buchholz、Piet W. N. M. van Leeuwen

  DOI：10.1021/ja100521m

  日期：2010.5.12

  prepared. They were used in the preparation of new monophosphine-palladium(0)-dvds complexes, which were employed as catalysts for the selective telomerization of 1,3-butadiene with methanol to obtain 1-methoxyocta-2,7-diene (1-MOD), the key intermediate in the Dow 1-octene process. Several ligands showed improved selectivity and yield compared to that of the benchmark ligand PPh(3). Especially 2,7-di-tert-butyl-9

  制备了一系列含有取代联苯、2-甲基萘基或 2,7-二-叔丁基-9,9-二甲基呫吨部分的庞大膦。它们用于制备新的单膦-钯 (0)-dvds 配合物，该配合物用作 1,3-丁二烯与甲醇选择性调聚得到 1-甲氧基辛基-2,7-二烯 (1-MOD) 的催化剂)，陶氏 1-辛烯工艺中的关键中间体。与基准配体 PPh(3) 相比，几种配体显示出更高的选择性和产量。特别是 2,7-二叔丁基-9,9-二甲基黄原酸-4-基-二苯基膦（4，“mono-xantphos”）在产率、选择性和稳定性方面是一种出色的配体。
• Ru^(II)-catalyzed P^(III)-assisted C8-alkylation of naphthphosphines
  作者：Wen-Tao Ma、Mao-Gui Huang、Yueliuting Fu、Zhong-Hui Wang、Jun-Yang Tao、Jia-Wei Li、Yue-Jin Liu、Ming-Hua Zeng

  DOI：10.1039/d2cc02161g

  日期：——

  We report a phosphine-directed ruthenium-catalyzed C8-selective alkylation of naphthalenes with alkenes. This protocol provides straightforward access to a large library of electron-rich C8-alkyl substituent 1-naphthphosphines, which outperformed common commercial phosphines and their precursors in the Pd-catalyzed Suzuki–Miyaura coupling of aryl bromides with alkylboronic acid.

  我们报告了萘与烯烃的膦定向钌催化的 C8 选择性烷基化。该协议提供了对富含电子的 C8-烷基取代基 1-萘膦的大型库的直接访问，该库在芳基溴化物与烷基硼酸的 Pd 催化 Suzuki-Miyaura 偶联中优于常见的商业膦及其前体。
• Synthesis and characterization of phospha-palladacycles and their catalytic properties in the olefination of chloro- and bromoarenes
  作者：Guido D. Frey、Claus-Peter Reisinger、Eberhardt Herdtweck、Wolfgang A. Herrmann

  DOI：10.1016/j.jorganchem.2005.03.052

  日期：2005.7

  Acetylacetonates of phospha-palladacycles are new catalysts in the Heck coupling of aryl chlorides and bromides with styrene. Turnover numbers (TON) of much higher than 300,000 and product yields up to 99% are obtained. (c) 2005 Elsevier B.V. All rights reserved.
• o-Alkyl-substituted aromatic phosphanes for hydroformylation studies: synthesis, spectroscopic characterization and ab initio investigations
  作者：Helena Riihimäki、Pekka Suomalainen、Heidi K Reinius、Johanna Suutari、Sirpa Jääskeläinen、A.O.I Krause、Tapani A Pakkanen、Jouni T Pursiainen

  DOI：10.1016/s1381-1169(03)00022-0

  日期：2003.6

  In earlier hydroformylation studies modification of the rhodium catalyst with o-methyl-substituted or o-ethyl-substituted phosphane ligands have increased regioselectivity to branched aldehydes. The promising results achieved created a need for further studies. Hence, a wider group of o-substituted arylphosphane ligands, e.g. (2-cyclohexylphenyl)diphenylphosphane, (2-isopropylphenyl)diphenylphosphane, (2-methylnaphthyl)diphenylphosphane, (2,5-dimethylphenyl)diphenylphosphane and (2-phenylphenyl)diphenylphosphane were synthesized and tested in rhodium-catalyzed hydroformylation to support the,previous findings. Characterization of the ligands was made by NMR spectroscopy (H-1, P-31H-1}, C-13H-1}, HSQC, COSY-90 and COLOC). Additional parameters for evaluation of the stereoelectronic properties of the ligands were provided by quantum mechanical calculations and by synthesizing Rh(acac)(CO)(PR3) Complexes. In the rhodium-catalyzed hydroformylation of propene and 1-hexene the ligands increased the formation of branched aldehydes compared to triphenylphosphane. Additionally the increasing size of the o-alkyl-substituent was found to effect favorably to the iso-selectivity. (C) 2003 Elsevier Science B.V. All rights reserved.