10-hydroxy-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide | 36240-31-0

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 10-hydroxy-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide
• 英文别名: 6-hydroxy-6H-dibenzo [c,e][1,2]oxaphosphinine 6-oxide；DOPO-OH；6-hydroxybenzo[c][2,1]benzoxaphosphinine 6-oxide
• CAS: 36240-31-0
• 化学式: C₁₂H₉O₃P
• 分子量: 232.175
• InChiKey: YTLIXUAGIGBJAF-UHFFFAOYSA-N

物化性质

• 熔点：
  198-199 °C
• 沸点：
  455.2±28.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  10-hydroxy-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide 在 氯化亚砜 作用下， 反应 18.0h， 以92%的产率得到10-chloro-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide
  参考文献：
  名称：

  Process for preparing 10-chloro-9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide compound

  摘要：

  提供了一种制备10-氯-9,10-二氢-9-氧-10-磷代菲-10-氧化物（DOPO-C）化合物的过程，该过程包括以下步骤：将液体氯化剂与由式（B）表示的9,10-二氢-10-羟基-9-氧-10-磷代菲-10-氧化物化合物反应，形成混合物，该混合物包含由式（A）表示的DOPO-C化合物和未反应的液体氯化剂，将DOPO-C化合物和未反应的液体氯化剂从混合物中分离出来，以获得DOPO-C化合物；其中X1、X2和X3分别独立地选自氢原子、羟基、氰基、磺酸基、由—SO3R1表示的磺酸酯基、卤素原子、由—OR2表示的烷氧基、具有1至8个碳原子的非环烃基、具有3至8个碳原子的环烷基、芳基、杂环芳基和芳基烷基的群，其中R1和R2分别是具有1至8个碳原子的非环烃基。

  公开号：

  US08703986B1
• 作为产物：
  描述：

  10-氯-9,10-二氢-9-氧杂-10-磷杂菲 在 双氧水 作用下， 以 乙醇 为溶剂， 生成 10-hydroxy-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide
  参考文献：
  名称：

  Chernyshev,E.A. et al., Journal of general chemistry of the USSR, 1972, vol. 42, p. 88 - 90

  摘要：

  DOI：

文献信息

• DCC-assisted direct esterification of phosphinic and phosphoric acids with <i>O</i>-nucleophiles
  作者：Biquan Xiong、Gang Wang、Congshan Zhou、Yu Liu、Jiandong Li、Pangliang Zhang、Kewen Tang

  DOI：10.1080/10426507.2017.1395438

  日期：2018.4.3

  -promoted protocol for the selective and controllable esterification of P(O)OH compounds using O-nucleophiles (alcohols and phenols) as efficient esterification reagents is described. This method features a high efficiency and good functional-group tolerance, meaning a simple way to synthesize a broad spectrum of phosphinic and phosphoric acid esters from basic starting materials with moderate to excellent

  图形摘要 摘要描述了使用 O-亲核试剂（醇和酚）作为有效酯化试剂对 P(O)OH 化合物进行选择性和可控酯化的新型高效二环己基碳二亚胺促进方案。该方法具有高效率和良好的官能团耐受性，这意味着一种简单的方法可以从碱性原料合成广谱的次膦酸酯和磷酸酯，收率中等至极好。
• 一种以含P(O)-OH类化合物与醇高效酯化制 备有机膦酸酯类化合物的方法
  申请人：湖南理工学院

  公开号：CN106749396B

  公开（公告）日：2020-12-15

  本发明提供了一种高效、高选择性合成含不同取代官能团的有机膦酸酯类衍生物的方法，其采用多肽催化剂作为缩合试剂，以含P(O)‑OH类化合物与醇作为反应底物，反应体系加入了有机溶剂。该方法的优点：催化剂廉价易得；底物适用性高；反应条件温和，安全可靠；所得目标产物的选择性接近100%，产率高达90%以上。该方法解决了传统合成有机膦酸酯类化合物的反应选择性差、反应步骤繁琐、产率低以及需要用到对环境有害试剂等不足，具有良好的工业应用前景。本发明同时还提供了对应的含不同取代官能团的有机膦酸酯类衍生物。
• CDI-promoted direct esterification of P(O)-OH compounds with phenols
  作者：Biquan Xiong、Chenghong Hu、Haotian Li、Congshan Zhou、Pangliang Zhang、Yu Liu、Kewen Tang

  DOI：10.1016/j.tetlet.2017.05.036

  日期：2017.6

  efficient N,N′-carbonyl diimidazole-catalyzed protocol for the direct esterification of P(O)-OH compounds using phenols as efficient esterification reagents is illustrated. It is a simple way to synthesis a broad spectrum of functionalized O-aryl phosphinates, phosphonates, and phosphates from basic starting materials with moderate to excellent yields.

  说明了一种新颖且有效的N，N'-羰基二咪唑催化的方法，用于使用酚作为有效酯化剂的P（O）-OH化合物的直接酯化。这是一种简单的方法，可以从碱性原料中以中等到极好的收率合成各种功能化的O-芳基次膦酸酯，膦酸酯和磷酸盐。
• Organic–inorganic hybrid flame retardant: preparation, characterization and application in EVA
  作者：Li Yu、Li Chen、Liang-Ping Dong、Liang-Jie Li、Yu-Zhong Wang

  DOI：10.1039/c4ra00700j

  日期：——

  A novel organic–inorganic hybrid flame retardant (DOPA–ATH), which was prepared via reacting dibenzo[c,e][1,2]oxaphosphinic acid (DOPA) with aluminum trihydroxide (ATH), was incorporated in ethylene-vinyl acetate copolymer (EVA) to improve its flame retardance. The structure, morphology and thermal stability of the hybrid flame retardant were characterized by Fourier transform infrared spectroscopy (FTIR), Raman spectroscopy, X-ray diffraction (XRD), scanning electron microscopy (SEM), and thermogravimetric analysis (TGA). The results suggested that DOPA was grafted onto ATH successfully, therefore resulting in higher thermostability than ATH. The flame retardance and burning behaviour of EVA with DOPA–ATH were also studied using limiting oxygen index (LOI), Underwriter laboratory 94 vertical burning test (UL-94 V) and cone calorimeter test (CCT). Results of UL-94 tests and LOI tests showed that the flame retardance of EVA/DOPA–ATH was better than EVA/ATH binary and EVA/DOPA/ATH ternary flame-retardant composites. The data obtained from the CCT showed that the peak heat release rate (PHRR) of EVA with the addition of 50 wt% DOPA–ATH was reduced by about 25% comparing with EVA with equivalent ATH. Total heat release (THR) and total smoke production (TSP) were reduced remarkably as well. The thermogravimetric analysis (TGA) data showed that the thermal stability of EVA/DOPA–ATH was improved with increased initial decomposition temperature and char residue. SEM observations of cryogenically fractured and tension fractured surfaces showed that EVA/DOPA–ATH had better interfacial interaction comparing with those of EVA/ATH and EVA/DOPA/ATH, which resulted in better elongation at break and tensile strength.

  一种新型有机-无机杂化阻燃剂(DOPA-ATH),通过二苯并[c,e][1,2]氧膦酸(DOPA)与三水合氧化铝(ATH)反应制备而成,用于乙烯-醋酸乙烯酯共聚物(EVA)中以提高其阻燃性能。杂化阻燃剂的结构、形貌和热稳定性通过傅里叶变换红外光谱(FTIR)、拉曼光谱、X射线衍射(XRD)、扫描电子显微镜(SEM)和热重分析(TGA)进行表征。结果表明,DOPA成功接枝到ATH上,因此热稳定性高于ATH。通过极限氧指数(LOI)、美国保险商实验室94垂直燃烧试验(UL-94V)和锥形量热仪试验(CCT)研究了EVA与DOPA-ATH的阻燃性和燃烧行为。UL-94和LOI测试结果显示,EVA/DOPA-ATH的阻燃性能优于EVA/ATH二元和EVA/DOPA/ATH三元阻燃复合材料。从CCT获得的数据表明,与等量ATH的EVA相比,添加50 wt% DOPA-ATH的EVA的峰值热释放速率(PHRR)降低了约25%。总热释放量(THR)和总烟雾产生量(TSP)也显著降低。热重分析(TGA)数据表明,EVA/DOPA-ATH的热稳定性随着初始分解温度的升高和残碳量的增加而提高。低温断裂和拉伸断裂表面的SEM观察显示,EVA/DOPA-ATH的界面相互作用优于EVA/ATH和EVA/DOPA/ATH,从而导致更好的断裂伸长率和拉伸强度。
• Coordination Compounds of 9,10‐Dihydro‐9‐oxa‐10‐phosphaphenanthrene‐10‐Oxide (DOPO) Ligands: Extremely High Thermostability and Ligand Oxidation in the Solid State
  作者：Daniela Goedderz、Timmy Schäfer、Johannes Klitsch、Lais Weber、Bettina Weber、Olaf Fuhr、Gerd Buntkowsky、Frank Schönberger、Manfred Döring

  DOI：10.1002/ejic.202000269

  日期：2020.7.7

  phosphinates and phosphonates were obtained containing zinc, calcium and magnesium as cations by means of a salt metathesis reaction with sodium salts of DOPO and DOPO‐OH. The synthesized complexes [Zn(DOPO)2]n , [Zn(DOPO‐OH)2]n and [Ca(DOPO)2(H2O)]n are featured a polymeric structure. The open‐ring metal phosphinate coordination compound [Zn(DOPO)2]n is able to undergo a non‐reversible thermally induced

  通过与DOPO和DOPO-OH的钠盐进行盐复分解反应，获得了包含锌，钙和镁作为阳离子的不同金属次膦酸盐和膦酸盐。合成的配合物[Zn（DOPO）2 ] n ，[Zn（DOPO-OH）2 ] n 和[Ca（DOPO）2（H 2 O）] n 具有聚合物结构。开环金属次膦酸酯配位化合物[Zn（DOPO）2 ] n 能够经历不可逆的热诱导氧化环化反应生成相应的金属膦酸酯[Zn（DOPO-OH）2 ] n 。次膦酸镁和钙不能被氧化成其相应的金属膦酸酯配合物。通过X射线晶体学，NMR，TGA和TDMS分析了所有有机磷化合物。用DSC研究了[Zn（DOPO）2 ] n 的氧化环化反应。另外，配位聚合物[Zn（DOPO）2 ] n 可以通过添加氮配体（例如N-甲基咪唑）而转变成分子复合物，从而使膦酸酯配体从桥联配体变为单齿配体。合成的配位化合物表现出非常高的热稳定性，最高可达520°C。