2-phenyl-2-oxo-5,6-benzo-1,3,2-dioxaphosphepane | 133611-21-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 2-phenyl-2-oxo-5,6-benzo-1,3,2-dioxaphosphepane
• 英文别名: 2-phenyl-2-oxo-5,6-benzo-1,3,2-dioxaphosphepine；2,4,3-Benzodioxaphosphepin, 1,5-dihydro-3-phenyl-, 3-oxide；3-phenyl-1,5-dihydro-2,4,3λ5-benzodioxaphosphepine 3-oxide
• CAS: 133611-21-9
• 化学式: C₁₄H₁₃O₃P
• 分子量: 260.229
• InChiKey: ZAFSLNWLKWPIJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻苯二甲醇 在 双氧水 、 三溴化磷 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 2-phenyl-2-oxo-5,6-benzo-1,3,2-dioxaphosphepane
  参考文献：
  名称：

  新型 3 取代 1,5-dihydro-2,4,3-benzodioxaphosphepine 3-oxides 的合成和抗菌活性

  摘要：

  在三乙胺存在下，在 0-30°C 下，通过 1,2-苯二甲醇 (1) 与三溴化磷反应，合成了新型 3 取代的 1,5-二氢-2,4,3-苯并二氧杂膦 3-氧化物 (5a-h)以及随后单溴化物 (2) 与不同格氏试剂 (3) 在室温下的反应。通过在室温下用 H2O2 氧化，产物 (4) 被转化为相应的氧化物 5a-i。所有产品的化学结构均通过分析、IR 和 NMR（1H、13C 和 31P）光谱数据确认。还评估了它们的抗真菌和抗菌活性。大多数这些化合物在试验中表现出中等的抗微生物活性。© 2005 Wiley Periodicals, Inc. 杂原子化学 16:572–575, 2005; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20154

  DOI：

  10.1002/hc.20154

文献信息

• Molecular and crystal structure of 2-phenyl-2-oxo-5,6 -benzo-1,3,2-dioxaphosphepine
  作者：I. A. Litvinov、O. N. Kataeva、V. A. Naumov、R. P. Arshinova、S. G. Gnevashev

  DOI：10.1007/bf00959663

  日期：1991.1

  The seven-membered heterocycle in the crystal structure of 2-phenyl-2-oxo-5,6-benzo-1,3,2-dioxaphosphepine has distorted (asymmetric) twist conformation and the plane of the phenyl substituent at the phosphorus atom does not coincide with the bisector of the plane of the OPO fragment of the heterocycle and is not perpendicular to it.
• Conformational analysis of 2-phenyl-2-oxo-5,6-benzo-1,3,2-dioxaphosphepine with data from vibrational spectroscopy, dipole moments, and the kerr effect
  作者：I. Kh. Shakirov、R. R. Shagidullin、S. G. Gnevashev、R. P. Arshinova

  DOI：10.1007/bf00961351

  日期：1991.5

  2-Phenyl-2-oxo-5,6-benzo-1,3,2-dioxaphosphepine exists in a melt and solutions in polar solvents as a three-component equilibrium of two chair forms (C) with axial and equatorial arrangement of the phenyl group and the twist-boat form (TB) with a pseudoequatorial position of the phenyl substituent, a-C reversible e-C reversible e-TB. The two-component equilibrium e-C reversible e-TB is observed in nonpolar solvents. The e-TB conformation occurs in the crystalline state. The dipole moment of the P = O groups is 3.5 D. The angle of rotation of the plane of the phenyl group with respect to the P = O bond in the e-TB conformation was 54 or 129-degrees.
• Synthesis and conformational analysis of torsionally constrained 1,3,2-dioxaphosphepanes
  作者：William N. Setzer、Milton L. Brown、Xiao Jing Yang、Melody A. Thompson、Kylen W. Whitaker

  DOI：10.1021/jo00036a011

  日期：1992.5

  A series of benzo-fused and norbornene-fused 1,3,2-dioxaphosphepanes have been synthesized and conformationally studied by proton and phosphorus-31 NMR, infrared spectroscopy, and X-ray crystallography. The NMR data are best interpreted in terms of chair-chair equilibria in which substituents on phosphorus (phenoxy, dimethylamino, and phenyl) show a remarkable preference for axial positions. Twist conformations cannot be completely ruled out, however. X-ray crystal structures have been determined for two of the norbornene-fused compounds, trans-5,6-(endo,endo-2',3'-bicyclo[2.2.1]hept-5'-eno)-2-oxo-2-phenoxy-1,3,2-dioxaphosphepane (trans-2a) and trans-5,6-(endo,endo-2',3'-bicyclo[2.2.l]hept-5'-eno)-2-oxo-2-phenyl-1,3,2-dioxaphosphepane (trans-2b), and one of the benzo-fused compounds, 5,6-benzo-2-oxo-2-phenyl-1,3,2-dioxaphosphepane (1b). The X-ray structures of the two norbornene-fused dioxaphosphepanes confirm the stereochemical assignments for these materials and show the seven-membered ring to adopt a chair conformation. A twist conformation is seen in the structure of the benzo-fused dioxaphosphepane, on the other hand.
• Synthesis and antimicrobial activity of novel 3 substituted 1,5-dihydro-2,4,3-benzodioxaphosphepine 3-oxides
  作者：P. Haranath、M. F. Stephen Babu、U. Anasuyamma、C. Naga Raju、C. Suresh Reddy

  DOI：10.1002/hc.20154

  日期：——

  Novel 3 substituted 1,5-dihydro-2,4,3-benzodioxaphosphepine 3-oxides (5a–h) were synthesized by reacting 1,2-benzenedimethanol (1) with phosphorus tribromide in the presence of triethylamine at 0–30°C and subsequent reaction of the monobromide (2) with different Grignard reagents (3) at room temperature. The products (4) were converted to corresponding oxides 5a–i by oxidation with H2O2 at room temperature

  在三乙胺存在下，在 0-30°C 下，通过 1,2-苯二甲醇 (1) 与三溴化磷反应，合成了新型 3 取代的 1,5-二氢-2,4,3-苯并二氧杂膦 3-氧化物 (5a-h)以及随后单溴化物 (2) 与不同格氏试剂 (3) 在室温下的反应。通过在室温下用 H2O2 氧化，产物 (4) 被转化为相应的氧化物 5a-i。所有产品的化学结构均通过分析、IR 和 NMR（1H、13C 和 31P）光谱数据确认。还评估了它们的抗真菌和抗菌活性。大多数这些化合物在试验中表现出中等的抗微生物活性。© 2005 Wiley Periodicals, Inc. 杂原子化学 16:572–575, 2005; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20154