10-phenyl-10λ⁵-phenoxaphosphine 10-oxide | 1091-27-6

• 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: 10-phenyl-10λ⁵-phenoxaphosphine 10-oxide
• 英文别名: 10-phenyl-10H-phenoxaphosphinine 10-oxide；10-phenyl-10H-phenoxaphosphine 10-oxide；10-phenylphenoxaphosphine 10-oxide；10-phenyl-10H-phenoxaphosphine 10-oxide；10-phenyl-10H-phenoxaphosphin-10-oxide；10-Phenyl-10H-phenoxaphosphin-10-oxid；10-phenylphenoxaphosphinine 10-oxide
• CAS: 1091-27-6
• 化学式: C₁₈H₁₃O₂P
• 分子量: 292.274
• InChiKey: XTSYWNMFJLRCLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  10-phenyl-10λ⁵-phenoxaphosphine 10-oxide 在 氢氧化钾 作用下， 以60%的产率得到(2-苯氧基苯基)-苯基次膦酸
  参考文献：
  名称：

  Skvortsov, N. K.; Toldov, S. V.; Bel'skii, V. K., Russian Journal of General Chemistry, 1994, vol. 64, # 4.1, p. 550 - 553

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2-dilithiumdiphenyl ether 在 双氧水 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 3.17h， 生成 10-phenyl-10λ⁵-phenoxaphosphine 10-oxide
  参考文献：
  名称：

  Toldov, S. V.; Kostenko, N. L.; Bel'skii, V. K., Journal of general chemistry of the USSR, 1990, vol. 60, # 6, p. 1120 - 1127

  摘要：

  DOI：

文献信息

• The alkaline hydrolysis of some cyclic phosphonium salts: ring-opening and ring-expansion reactions
  作者：David W. Allen、Ian T. Millar

  DOI：10.1039/j39690000252

  日期：——

  The alkaline hydrolysis of some five- and six-membered cyclic phosphonium salts has been examined, and the results have been related to current views on the structure and stereochemistry of the phosphorane intermediates of such reactions.

  已经研究了一些五元和六元环状phospho盐的碱水解，其结果与有关此类反应的膦烷中间体的结构和立体化学的当前观点有关。
• Palladium-Catalyzed Synthesis of Six-Membered Benzofuzed Phosphacycles via Carbon–Phosphorus Bond Cleavage
  作者：Katsuaki Baba、Mamoru Tobisu、Naoto Chatani

  DOI：10.1021/ol503252t

  日期：2015.1.2

  The palladium-catalyzed synthesis of dibenzofused six-membered phosphacycles via carbon–phosphorus bond cleavage is developed. This method is compatible with a range of functional groups, such as esters, amides, and carbamates, which is in sharp contrast to the limitations of the classical method using organolithium reagents.

  开发了通过碳-磷键裂解的钯催化合成二苯并稠合六元磷环化合物。该方法与一系列官能团（例如酯，酰胺和氨基甲酸酯）兼容，这与使用有机锂试剂的传统方法的局限性形成鲜明对比。
• New Access to Six-Membered Phosphacycle Annulated Polyaromatic Ring System
  作者：Erbing Si、Peng Zhao、Lili Wang、Zheng Duan、François Mathey

  DOI：10.1002/ejoc.201901753

  日期：2020.2.14

  A facile access to six‐membered phosphacycle annulated polyaromatic ring system through Ag‐catalyzed intramolecular C–P bond formation reaction, from easily accessible phosphine oxides, has been developed, Several new heteroatoms fused π‐conjugated molecules were synthesized from this procedure with their structures confirmed by X‐ray structure analysis.

  通过易于催化的氧化膦，通过Ag催化的分子内C-P键形成反应，可轻松访问六元磷环环氧基的多芳族环系统。通过该程序合成了几种新的杂原子稠合的π-共轭分子，其结构通过X射线结构分析确认。
• Cyclization of Bisphosphines to Phosphacycles via the Cleavage of Two Carbon–Phosphorus Bonds by Nickel Catalysis
  作者：Hayato Fujimoto、Momoka Kusano、Takuya Kodama、Mamoru Tobisu

  DOI：10.1021/acs.orglett.9b01355

  日期：2019.6.7

  The nickel-catalyzed cyclization of bisphosphine derivatives to form various phosphacycles is reported. The reaction proceeds via the cleavage of two carbon–phosphorus bonds of the bisphosphine. Unlike the previously reported palladium catalysts, the use of nickel as a catalyst allows for the cyclization that requires C(alkyl)–P bond cleavage. A phospha-nickelacycle intermediate was successfully isolated

  据报道双膦衍生物在镍催化下环化形成各种磷环。该反应通过双膦的两个碳-磷键的裂解而进行。与先前报道的钯催化剂不同，使用镍作为催化剂可实现需要C（烷基）-P键断裂的环化反应。磷-nickelacycle中间体已成功分离，并通过X射线晶体学进行了表征。
• Palladium-catalyzed Cyclization of Bisphosphines to Phosphacycles via the Cleavage of Two Carbon–Phosphorus Bonds
  作者：Katsuaki Baba、Yoshihiro Masuya、Naoto Chatani、Mamoru Tobisu

  DOI：10.1246/cl.170581

  日期：2017.9.5

  A catalytic method for the synthesis of dibenzophosphole derivatives using bisphosphines as the starting material is developed. The reaction proceeds through the cleavage of two carbon–phosphorus bonds of the bisphosphine substrate. The reaction can also be used in the synthesis of six-membered phosphacycles.

  开发了一种以双膦为原料合成二苯并磷衍生物的催化方法。该反应通过双膦底物的两个碳-磷键的断裂而进行。该反应还可用于合成六元磷酸环。