trityl-phosphonic acid diethyl ester | 63923-56-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: trityl-phosphonic acid diethyl ester
• 英文别名: diethyl triphenylmethylphosphonate；diethyl tritylphosphonate；Ph3CP(O)(OEt)2；TrPO(OEt)2；Triphenylmethylphosphonsaeure-diaethylester；Trityl-phosphonsaeure-diaethylester；Diethyl (triphenylmethyl)phosphonate；[diethoxyphosphoryl(diphenyl)methyl]benzene
• CAS: 63923-56-8
• 化学式: C₂₃H₂₅O₃P
• 分子量: 380.423
• InChiKey: AEMDEBJSSOOMNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trityl-phosphonic acid diethyl ester 在 五氯化磷 、 苯 作用下， 生成 ditrityl-diphosphonic acid diethyl ester
  参考文献：
  名称：

  191.三苯甲烷某些磷衍生物的组成

  摘要：

  DOI：

  10.1039/jr9330000776
• 作为产物：
  描述：

  trityl tetrafluoroborate 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 trityl-phosphonic acid diethyl ester
  参考文献：
  名称：

  Dimroth,K.; Nuerrenbach,A., Chemische Berichte, 1960, vol. 93, p. 1649 - 1658

  摘要：

  DOI：

文献信息

• Photolysis of Triarylmethylphosphonic Acids and Their Esters
  作者：Min Shi、Yoshiki Okamoto、Setsuo Takamuku

  DOI：10.1246/bcsj.63.453

  日期：1990.2

  Upon UV-irradiation in an alkaline alcohol solution, some triarylmethylphosphonic acids underwent C–P bond cleavage to give triarylmethanes and alkyl dihydrogenphosphates, while, in an acidic or a neutral alcohol solution, they afforded biaryls. Their dimethyl esters gave also biaryls and dimethyl [alkoxy(aryl)methyl]phosphonates, which were derived from the insertion of (dialkoxyphosphinyl)arylcarbenes

  在碱性醇溶液中紫外线照射后，一些三芳基甲基膦酸发生 C-P 键断裂，得到三芳基甲烷和磷酸二氢烷基酯，而在酸性或中性醇溶液中，它们得到联芳基化合物。它们的二甲酯也产生联芳基和 [烷氧基（芳基）甲基]膦酸二甲酯，它们源自（二烷氧基膦基）芳基卡宾插入醇的 OH 键。卡宾是通过光-α,α-消除膦酸酯的两个芳基而产生的。
• The Complex Role of the Triphenylmethyl Motif in Anticancer Compounds
  作者：Rahul Palchaudhuri、Vitaliy Nesterenko、Paul J. Hergenrother

  DOI：10.1021/ja8020999

  日期：2008.8.1

  Compounds incorporating the triphenylmethyl motif constitute an emerging family of potent anticancer agents. Although several small molecules containing this pharmacophore have now been identified, the mechanism of cell death induction for some of these compounds is unknown. In an effort to define their mechanism of action, and to distinguish subtypes within the group of compounds containing the triphenylmethyl

  包含三苯甲基基序的化合物构成了一个新兴的强效抗癌剂家族。虽然现在已经鉴定了几种含有这种药效团的小分子，但其中一些化合物的细胞死亡诱导机制尚不清楚。为了确定它们的作用机制，并区分含有三苯甲基部分的化合物组中的亚型，我们创造了新的含有三苯甲基的小分子，并在一系列生物测定中对其进行了评估。在这里，我们展示了几种具有三苯甲基基序的膦酸盐和膦酰氯，可有效诱导培养中多种癌细胞系的死亡。评估导致细胞周期停滞、抑制微管蛋白聚合的能力的进一步分析，
• A highly efficient nucleophilic substitution reaction between R₂P(O)H and triarylmethanols to synthesize phosphorus-substituted triarylmethanes
  作者：Long Chen、Xin-Yue Fang、Yun-Xiang Zou

  DOI：10.1039/c7ob02970e

  日期：——

  A highly efficient and general nucleophilic substitution reaction between dialkyl H-phosphonates or diarylphosphine oxides and triarylmethanols catalyzed by HOTf (trifluoromethanesulfonic acid) has been developed. It provides an atom-economical protocol for the synthesis of various symmetrical and unsymmetrical phosphorus-substituted triarylmethanes that constitute an emerging family of potent anticancer

  已经开发了由HOTf（三氟甲磺酸）催化的H-膦酸二烷基酯或二芳基膦氧化物与三芳基甲醇之间的高效且通用的亲核取代反应。它为合成各种对称和不对称的磷取代的三芳基甲烷提供了一种原子经济的方法，这些化合物构成了新兴的强效抗癌剂家族，具有丰富的多样性，产率为40％至96％。该协议的综合适用性已通过克量级的制备证明。
• A Facile Synthesis and Crystallographic Analysis of Seven Trityl Phosphorus Compounds and Two Nickel(II) Phosphine Side-Products
  作者：Audra F. Gushwa、Yamina Belabassi、Jean-Luc Montchamp、Anne F. Richards

  DOI：10.1007/s10870-008-9481-0

  日期：2009.5

  The syntheses and X-ray analyses of triphenylmethyl (trityl=Tr) phosphorus compounds are reported and the structural similarities, differences and 31P chemical shifts compared. A series of seven trityl-substituted phosphorus-containing compounds have been characterized by single crystal X-ray diffraction. Ph3CPPh2, 1, a bulky P(III) compound crystallizes in the triclinic space group $$ \textP}}\overline1} $$ , a = 7.5624(6) Å, b = 9.5470(8) Å, c = 16.9722(14) Å, α = 83.4720(10)°, β = 80.541(2)°, γ = 68.1580(10)°, the borane complex of 1, 2, Ph3CPPh2(BH3) crystallizes as monoclinic colorless crystals, P21/c, a = 10.0972(12) Å, b = 9.6955(12) Å, c = 25.197(3) Å, β = 90.258(2)°. The analogous methyl substituted, 3, Ph3CPMe2(BH3) is monoclinic, C2/c, a = 15.628(3) Å, b = 12.770(3) Å, c = 18.406(4) Å, β = 103.968(3)°. Compounds 4–7 are trityl substituted P(V) compounds: Ph3CP(Ph)(O)(OH), 4, crystallizes in the triclinic space group $$ \textP}}\overline1} $$ , a = 8.9847(18) Å, b = 9.7443(19) Å, c = 12.786(3) Å, α = 72.045(3)°, β = 72.031(3)°, γ = 78.769(3)°. Esterification of 4 affords TrCP(O)(Ph)OBn 5, space group, P21/c, a = 7.9196(5) Å, b = 31.701(2) Å, c = 19.8062(13) Å, β = 99.7750(10)°. A phosphonate diester was also characterized, Ph3CP(O)(OEt)2, 6, triclinic, $$ \textP}}\overline1} $$ , a = 7.9521(17) Å, b = 9.2205(19) Å, c = 14.471(3) Å, α = 85.906(4)°, β = 83.031(4)°, γ = 68.283(4)°. Treatment of the trityl H-phosphinic acid, Ph3CPO2H2, with elemental selenium yields yellow crystals of 7, [Ph3CP(O)(OH)Se]2, P21/c, a = 9.0603(4) Å, b = 22.3652(11) Å, c = 16.9134(7) Å, β = 107.035(2)°. In our efforts to isolate a nickel-phosphine complex, two Ni(II) complexes were crystallographically analyzed, [Ni(OP(H)Ph2)6]2BF4 − 8 and 9. Complex 8 with an uncoordinated BF4 − ion crystallizes as yellow orthorhombic crystals, Pbca, a = 18.8247(12) Å, b = 18.5518(12) Å, c = 21.0976(14) Å, while crystals of 9 are trigonal, $$ \text R} \bar 3} \text c} $$ , a = b = 13.1545(12) Å, c = 68.461(9) Å. The syntheses and X-ray analyses of triphenylmethyl (trityl=Tr) phosphorus compounds are reported and the structural similarities, differences and 31P chemical shifts compared.

  报告了三苯甲基（triityl=Tr）磷化合物的合成和 X 射线分析，并比较了其结构的相似性、差异性和 31P 化学位移。单晶 X 射线衍射表征了七种三苯甲基含磷化合物系列。Ph3CPPh2, 1 是一种大分子 P（III）化合物，在三菱空间群 $$ \P}}\overline1} $$ 中结晶，a = 7。5624(6) Å, b = 9.5470(8) Å, c = 16.9722(14) Å, α = 83.4720(10)°, β = 80.541（2）°，γ = 68.1580（10）°，1，2，Ph3CPPh2（BH3）的硼烷络合物结晶为单斜无色晶体，P21/c，a = 10.0972(12) Å, b = 9.6955(12) Å, c = 25.197(3) Å, β = 90.258(2)°.类似的甲基取代物 3, Ph3CPMe2(BH3) 为单斜 C2/c，a = 15.628(3) 埃，b = 12.770(3) 埃，c = 18.406(4) 埃，β = 103.968(3)°。化合物 4-7 是三苯甲基取代的 P(V)化合物：Ph3CP(Ph)(O)(OH), 4 在三linic 空间群 $$ \textP}}\overline1} $$ 中结晶，a = 8.9847(18) Å, b = 9.7443(19) Å, c = 12.786(3) Å, α = 72.045(3)°, β = 72.031(3)°, γ = 78.769(3)°.4 的酯化反应生成 TrCP(O)(Ph)OBn 5，空间群，P21/c，a = 7.9196(5) 埃，b = 31.701(2) 埃，c = 19.8062(13) 埃，β = 99.7750(10)°。还表征了一种膦酸二酯，Ph3CP(O)(OEt)2, 6, 三菱形, $$ text\P}}\overline1} $$ , a = 7.9521(17) Å, b = 9.2205(19) Å, c = 14.471(3) Å, α = 85.906(4)°, β = 83.031(4)°, γ = 68.283(4)°.用硒元素处理三苯甲基 H-膦酸 Ph3CPO2H2，得到黄色晶体 7，[Ph3CP(O)(OH)Se]2，P21/c，a = 9。0603(4) Å, b = 22.3652(11) Å, c = 16.9134(7) Å, β = 107.035(2)°.为了分离出一种镍膦配合物，我们对两种镍（II）配合物进行了晶体分析，它们是 [Ni(OP(H)Ph2)6]2BF4 - 8 和 9。带有非配位 BF4 - 离子的络合物 8 结晶为黄色正方晶，Pbca, a = 18.8247(12) 埃，b = 18.5518(12) 埃，c = 21.0976(14) 埃。\bar 3} \text c} $$ , a = b = 13.1545(12) Å, c = 68.461(9) Å.报告了三苯甲基（tr=Tr）磷化合物的合成和 X 射线分析，并比较了其结构的相似性、差异性和 31P 化学位移。
• REACTIONS OF 4-ALKYL-1-TRITYL-1-PHOSPHA-2,6,7-TRIOXABICYCLO[2.2.2]OCTANE CATIONS WITH BASES
  作者：Yeping Zhou、Andrzej E. Wroblewski、John G. Verkade

  DOI：10.1080/10426509808036986

  日期：1998.1.1

  Abstract The syntheses of 4-alkyl-1-trityl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane tetrafluorobo-rates (alkyl group = Me, 4; Et, 5; r-Bu, 6) are described. Compounds 4, 5 and 6 in the presence of base (pyridine, DBU) or base (pyridine, DBU) plus H2O undergo Arbuzov ring opening reactions to give pyridinium salts or a mixture of hydrolyzed products and pyridinium salts, respectively. The configurations

  摘要 4-烷基-1-三苯甲基-1-磷酸-2,6,7-三氧杂双环[2.2.2]辛烷四氟硼酸酯的合成（烷基 = Me, 4; Et, 5; r-Bu, 6）被描述。在碱（吡啶，DBU）或碱（吡啶，DBU）加水存在下，化合物 4、5 和 6 进行 Arbuzov 开环反应，分别得到吡啶鎓盐或水解产物和吡啶鎓盐的混合物。产物的构型通过核磁共振光谱和 X 射线晶体学研究得到解决。还制备了无环三苯甲基盐 [(RO)3 CPh,]+BF4(R = Et, 7;新戊基, 8) 并进行了它们与碱或碱加 H2O 的反应，以与多环三苯甲基盐的反应进行比较.