trans-1,2-diphenyl-1,2-dihydronaphtho[1,8-cd][1,2]diphosphole

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: trans-1,2-diphenyl-1,2-dihydronaphtho[1,8-cd][1,2]diphosphole
• 英文别名: trans-naphthalene-1,8-diphenyldiphosphine；(2R,3R)-2,3-diphenyl-2,3-diphosphatricyclo[6.3.1.04,12]dodeca-1(11),4,6,8(12),9-pentaene
• 化学式: C₂₂H₁₆P₂
• 分子量: 342.317
• InChiKey: MNJNXGIXBLVTLE-DNQXCXABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  trans-1,2-diphenyl-1,2-dihydronaphtho[1,8-cd][1,2]diphosphole 以 正己烷 为溶剂， 以94%的产率得到cis-naphthalene-1,8-diphenyldiphosphine
  参考文献：
  名称：

  PhP–PPh group bound to 1,8-positions of naphthalene: Preparation of cis isomer and synthesis of binuclear complex

  摘要：

  A thermodynamically less stable cis isomer of 1,2-diphosphacycle was prepared from the corresponding trans isomer. Diphosphine, in which a PhP-PPh bond bridges the 1,8-positions of naphthalene, 1,2-diphenyl-1,2-dihydronaphtho[1,8-cd][1,2] diphosphole (1), was first prepared according to a previously reported method, and the trans isomer of 1 was irradiated in tetrahydrofuran with UV-vis light to reach equilibrium with cis-1 in a trans: cis ratio of 1:2. When a similar photochemical conversion was carried out using a saturated hexane solution of trans-1, cis-1 was precipitated in a good yield of 94%. The configuration of cis-1 was confirmed by X-ray analysis. Both cis-and trans-1 diphosphine ligands were used for the preparation of binuclear gold complexes. The crystal structure of (mu-cis-1)-[AuCl](2) demonstrated that the two lone pairs of cis-1 are suitably directed for arrangement of the two gold centers in close proximity to each other. The two independent (mu-cis-1)-[AuCl](2) molecules in the crystal were found to form a dimer through the multiple intermolecular interaction among the gold centers. (C) 2011 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2011.07.030
• 作为产物：
  描述：

  1-溴代萘 、 苯基二氯化磷 在 正丁基锂 、 四甲基乙二胺 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 3.5h， 以1.9%的产率得到cis-naphthalene-1,8-diphenyldiphosphine
  参考文献：
  名称：

  PhP–PPh group bound to 1,8-positions of naphthalene: Preparation of cis isomer and synthesis of binuclear complex

  摘要：

  A thermodynamically less stable cis isomer of 1,2-diphosphacycle was prepared from the corresponding trans isomer. Diphosphine, in which a PhP-PPh bond bridges the 1,8-positions of naphthalene, 1,2-diphenyl-1,2-dihydronaphtho[1,8-cd][1,2] diphosphole (1), was first prepared according to a previously reported method, and the trans isomer of 1 was irradiated in tetrahydrofuran with UV-vis light to reach equilibrium with cis-1 in a trans: cis ratio of 1:2. When a similar photochemical conversion was carried out using a saturated hexane solution of trans-1, cis-1 was precipitated in a good yield of 94%. The configuration of cis-1 was confirmed by X-ray analysis. Both cis-and trans-1 diphosphine ligands were used for the preparation of binuclear gold complexes. The crystal structure of (mu-cis-1)-[AuCl](2) demonstrated that the two lone pairs of cis-1 are suitably directed for arrangement of the two gold centers in close proximity to each other. The two independent (mu-cis-1)-[AuCl](2) molecules in the crystal were found to form a dimer through the multiple intermolecular interaction among the gold centers. (C) 2011 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2011.07.030

文献信息

• Formation of a Hexacarbonyl Diiron Complex Having a Naphthalene-1,8-bis(phenylphosphido) Bridge and the Electrochemical Behavior of Its Derivatives
  作者：Yuichi Teramoto、Kazuyuki Kubo、Shoko Kume、Tsutomu Mizuta

  DOI：10.1021/om4006142

  日期：2013.12.9

  complexes can be protonated with the strong acid TfOH in CH2Cl2 to form cationic complexes having a μ-H bridge between the two iron centers. The parent hexacarbonyl complex 3 could act as a proton reduction catalyst at −2.0 V in the presence of TsOH as the proton source in CH2Cl2. When protonated complexes having MeCN or phosphine ligands were used, the proton reduction potentials catalyzed by these complexes

  所述的P-P键的顺式- 1个配体（μ-顺式- 1）的[Fe（CO）4 ] 2（顺式- 1 =萘-1,8- diphenyldiphosphine）通过CO解离后在两个铁中心切割从铁中心，尽管所P-P键的顺式- 1是立体化学与鲁棒萘基团稳定化，不象通常的二膦，缺乏这样的支持。将得到的（μ-nabip）的[Fe（CO）3 ] 2（3 ; nabip =萘-1,8-二（phenylphosphido））具有由bisphosphido桥连接的二铁芯。由于反式异构体（μ-反式- 1）的[Fe（CO）4 ] 2是在环境条件下稳定，顺两个的Fe（CO）的配置4个片段负责用于P-P键的断裂。的一个或两个终端CO配体3即PME：可以通过的MeCN和一系列膦配位体来代替3，PPH 3，顺式- 1，和反式- 1。有趣的是，人们发现，二膦顺- 1可以协调铁中心在一个不寻常κ 2形成三元环，这已通过NMR光谱和X射
• PhP–PPh group bound to 1,8-positions of naphthalene: Preparation of cis isomer and synthesis of binuclear complex
  作者：Yuichi Teramoto、Kazuyuki Kubo、Tsutomu Mizuta

  DOI：10.1016/j.jorganchem.2011.07.030

  日期：2011.10

  A thermodynamically less stable cis isomer of 1,2-diphosphacycle was prepared from the corresponding trans isomer. Diphosphine, in which a PhP-PPh bond bridges the 1,8-positions of naphthalene, 1,2-diphenyl-1,2-dihydronaphtho[1,8-cd][1,2] diphosphole (1), was first prepared according to a previously reported method, and the trans isomer of 1 was irradiated in tetrahydrofuran with UV-vis light to reach equilibrium with cis-1 in a trans: cis ratio of 1:2. When a similar photochemical conversion was carried out using a saturated hexane solution of trans-1, cis-1 was precipitated in a good yield of 94%. The configuration of cis-1 was confirmed by X-ray analysis. Both cis-and trans-1 diphosphine ligands were used for the preparation of binuclear gold complexes. The crystal structure of (mu-cis-1)-[AuCl](2) demonstrated that the two lone pairs of cis-1 are suitably directed for arrangement of the two gold centers in close proximity to each other. The two independent (mu-cis-1)-[AuCl](2) molecules in the crystal were found to form a dimer through the multiple intermolecular interaction among the gold centers. (C) 2011 Elsevier B. V. All rights reserved.