3,3',4,4'-tetramethyl-1,1'-biphospholyl | 86272-21-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3,3',4,4'-tetramethyl-1,1'-biphospholyl
• 英文别名: 3,4,3',4'-tetramethylbiphospholyl；1,1’-bis(3,4-dimethylphosphole)；3,4,3',4'-tetramethylbi-1,1'-phospholyl；1-(3,4-Dimethylphosphol-1-yl)-3,4-dimethylphosphole
• CAS: 86272-21-1
• 化学式: C₁₂H₁₆P₂
• 分子量: 222.207
• InChiKey: YGVZEDIOAJTMOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  3,3',4,4'-tetramethyl-1,1'-biphospholyl 在 sulfur 作用下， 以 甲苯 为溶剂， 反应 0.5h， 生成 2,2',3,3'-tetraphenyl-4,4',5,5'-tetramethyl-6,6'-bis(1-phosphanorborna-2,5-dienyl) P,P'-disulfide
  参考文献：
  名称：

  Bevierre, M. O.; Mercier, F.; Ricard, L., Bulletin de la Societe Chimique de France, 1992, # 1, p. 1 - 8

  摘要：

  DOI：
• 作为产物：
  描述：

  lithium 3,4-dimethylphospholide 在 四氯化钛 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以61%的产率得到3,3',4,4'-tetramethyl-1,1'-biphospholyl
  参考文献：
  名称：

  1-Trimethylstannylphospholes as precursors of η⁵-phospholyl complexes. Synthesis of (η⁵-phospholyl)trichlorotitanium(IV) complexes

  摘要：

  锂磷脂与 Me3SnCl 反应生成 1-三甲基锡磷脂，在甲苯和正己烷溶液中与 TiCl4 反应，生成（δ-5-膦酰基）三氯钛（IV）络合物。

  DOI：

  10.1039/c39880000770

文献信息

• The unexpected chemistry of a bis(phospholyl)acetylene
  作者：Matthew P. Duffy、Bruno Donnadieu、François Mathey

  DOI：10.1002/hc.20457

  日期：2008.7

  The reaction of lithium 3,4-dimethyl-phospholide with tetrachloroethylene gives the corresponding 1,2-bis(phospholyl)acetylene that has been characterized by X-ray crystal structure analysis of its bis(pentacarbonylmolybdenum) complex. The reaction with sulfur leads to the corresponding disulfide that spontaneously undergoes a self-condensation via a Diels--Alder cycloaddition between the CC triple

  3,4-二甲基磷化锂与四氯乙烯反应生成相应的 1,2-双（磷酰基）乙炔，其双（五羰基钼）配合物的 X 射线晶体结构分析已对其进行表征。与硫的反应导致相应的二硫化物通过 CC 三键和磷二烯体系之间的 Diels--Alder 环加成自发进行自缩合，在失去磷桥的芳构化后，得到相应的 1,2-双（磷酰基）苯。© 2008 Wiley Periodicals, Inc. 杂原子化学 19:537–541, 2008; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20457
• Asymmetric Phospha-Diels-Alder Reaction: A Stereoselective Approach towards P-Chiral Phosphanes through Diastereotopic Face Differentiation
  作者：Tobias Möller、Menyhárt B. Sárosi、Evamarie Hey-Hawkins

  DOI：10.1002/chem.201203671

  日期：2012.12.21

  Old principles, new chemistry: A facile stereoselective synthesis of P‐chiral phosphanes is described in which the principle of enantiotopic and diastereotopic face differentiation used in carbon chemistry is extended to a phosphorus atom in a planar environment, that is, 2H‐phospholes.

  旧原理，新化学方法：描述了对映异构的手性膦的轻松立体选择性合成，其中碳化学中使用的对映异构和非对映异构的面分化原理在平面环境中扩展为一个磷原子，即2 H磷脂。
• Synthesis and Molecular Structure of Bis(pentamethylcyclopentadienyl) Phospholyl- and Arsolylsamarium(III) Complexes: Influence of Steric and Electronic Factors
  作者：François Nief、Louis Ricard

  DOI：10.1021/om010317n

  日期：2001.9.1

  The title complexes could be easily synthesized respectively from the following biphospholyls: 2,3,4,5,2 ' ,3 ' ,4 ' ,5 ' -octamethylbi-1,1 ' -phospholyl (1); 3,4,3 ' ,4 ' -tetramethylbi-1,1 ' -phospholyl (2); 2,5,2 ' ,5 ' -tetra-tert-butylbi-1,1 ' -phospholyl (3), and CP*Sm-2 or Cp*Sm-2(Et2O) (Cp* = pentamethylcyclopentadienyl). 3,4,3 ' ,4 ' -Tetramethylbi-1,1 ' -arsolyl (4), a precursor of the new 3,4-dimethylarsolyl ligand, was prepared in three steps from the known 1-chloro-2,5-di(trimethylsilyl)-3,4-dimethylarsole (5). The reaction of 4 with CP*Sm-2 afforded the title complex 12. Although the unsubstituted bi-1,1 ' -phospholyl could be observed by NMR, it decomposed during the isolation, and thus the title complex 13 with the unsubstituted phospholyl was prepared from Cp*Sm-2(Et2O) and the new thallium phospholide 8, synthesized by metathesis of lithium phospholide with thallous ethoxide. Compounds 8-13 were characterized by X-ray crystallography. The solid state structures of complexes 9-13 vary depending on the substitution pattern on the phospholyl ligand. They can be eta (1)- or eta (5)-coordinated monomers (respectively 9 and 12), a mu:eta (1):eta (5)- symmetrical dimer (13), or even unsymmetrical dimers where both the eta (1)- and the mu:eta (1),eta (5)-coordination modes are found (10 and 11). These structures are discussed by taking into account the electronic and steric properties of the phospholyl and arsolyl ligands.
• Laporte, F.; Mercier, F.; Ricard, L., Bulletin de la Societe Chimique de France, 1993, vol. 130, p. 843 - 850
  作者：Laporte, F.、Mercier, F.、Ricard, L.、Mathey, F.

  DOI：——

  日期：——
• Preparation of 3,3',4,4'-tetramethyl-1,1'-biphospholyl and its reactions with iron and cobalt carbonyls. Synthesis and x-ray crystal structure of a phospholyl complex with a chain of four cobalt atoms
  作者：Serge Holand、Francois Mathey、Jean Fischer、Andre Mitschler

  DOI：10.1021/om50003a027

  日期：1983.9