diethyl α-hydroxy-α-(3-trifluoromethylphenyl)methylphosphonate | 86208-43-7

• 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: diethyl α-hydroxy-α-(3-trifluoromethylphenyl)methylphosphonate
• 英文别名: diethyl (hydroxy)(3-trifluoromethylphenyl)methylphosphonate；[m-(trifluoromethyl)-α-hydroxybenzyl]phosphonic acid diethyl ester；alpha-Hydroxy-3-(trifluoromethyl)benzylphosphonic acid diethyl ester；diethoxyphosphoryl-[3-(trifluoromethyl)phenyl]methanol
• CAS: 86208-43-7
• 化学式: C₁₂H₁₆F₃O₄P
• 分子量: 312.226
• InChiKey: AXTRALIICWRSHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲基磺酰氯 、 diethyl α-hydroxy-α-(3-trifluoromethylphenyl)methylphosphonate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 Methanesulfonic acid (diethoxy-phosphoryl)-(3-trifluoromethyl-phenyl)-methyl ester
  参考文献：
  名称：

  Stabilization demands of diethyl phosphonate substituted carbocations as revealed by substituent effects

  摘要：

  DOI：

  10.1021/jo00212a033
• 作为产物：
  描述：

  3-三氟甲基苯甲醛 在 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 diethyl α-hydroxy-α-(3-trifluoromethylphenyl)methylphosphonate
  参考文献：
  名称：

  Stabilization demands of diethyl phosphonate substituted carbocations as revealed by substituent effects

  摘要：

  DOI：

  10.1021/jo00212a033

文献信息

• Highly Efficient Hydrophosphonylation of Aldehydes and Unactivated Ketones Catalyzed by Methylene-Linked Pyrrolyl Rare Earth Metal Amido Complexes
  作者：Shuangliu Zhou、Zhangshuan Wu、Jiewei Rong、Shaowu Wang、Gaosheng Yang、Xiancui Zhu、Lijun Zhang

  DOI：10.1002/chem.201102207

  日期：2012.2.27

  characterized by 1H NMR spectroscopic analyses. The structures of complexes 2, 3, 4, and 6 were determined by single‐crystal X‐ray analyses. Study of the catalytic activities of the complexes showed that these rare earth metal amido complexes were excellent catalysts for hydrophosphonylations of aldehydes and unactivated ketones. The catalyzed reactions between diethyl phosphite and aldehydes in the presence

  通过甲硅烷基胺消除反应制备了一系列带有亚甲基连接的吡咯基-酰胺基配体的稀土金属酰胺配合物，在无溶剂条件下，液态底物在醛和未活化酮的氢膦酰化反应中显示出很高的催化活性。的治疗[（ME 3 Si）的2 N] 3 LN（μ-Cl）的锂（THF）3与2-（2,6--ME 2 ç 6 ħ 3 NHCH 2）C 4 H ^ 3 NH（1，1个当量）在甲苯，得到相应的式三价稀土金属酰胺（μ-η 5：η 1）：η 1-2-[（2,6-Me 2 C 6 H 3）NCH 2 ]（C 4 H 3 N）LnN（SiMe 3）2 } 2 [Ln = Y（2），Nd（3），Sm（4），Dy（5），Yb（6）]，产量适中。所有化合物均通过光谱法和元素分析充分表征。钇配合物的特征还在于1 H NMR光谱分析。复合物的结构 2，3，4，和6由单晶X射线分析确定。配合物催化活性的研究表明，这些稀土金属酰胺配合物是醛和未活化
• Efficient Synthesis of Acylated, Dialkyl α-Hydroxy-Benzylphosphonates and Their Anticancer Activity
  作者：Petra R. Varga、Alexandra Belovics、Péter Bagi、Szilárd Tóth、Gergely Szakács、Szilvia Bősze、Rita Szabó、László Drahos、György Keglevich

  DOI：10.3390/molecules27072067

  日期：——

  optical purity was retained. A part of the acyloxyphosphonates was tested against eight tumor cell lines of different tissue origin at c = 50 μM concentration. The compounds elicited moderate cytostatic effect against breast, skin, prostate, colon, and lung carcinomas; a melanoma cell line; and against Kaposi’s sarcoma cell lines. Then, dose-dependent cytotoxicity was assayed, and benzoylation of the

  开发了一种以酰氯为试剂对α-羟基苄基膦酸二烷基酯的受阻羟基进行酰化的有效方法。该程序不需要任何催化剂。S C也进行了一些酰化-α-羟基苄基膦酸二甲酯的对映异构体，并保持光学纯度。在 c = 50 μM 浓度下，针对八种不同组织来源的肿瘤细胞系测试了一部分酰氧基膦酸盐。这些化合物对乳腺癌、皮肤癌、前列腺癌、结肠癌和肺癌具有中等的细胞抑制作用；黑色素瘤细胞系；并针对卡波西肉瘤细胞系。然后，测定了剂量依赖性细胞毒性，并将 α-羟基的苯甲酰化确定为增加所有细胞系的抗癌细胞毒性的部分。令人惊讶的是，一些类似物对耐多药癌细胞系的毒性更大，从而避免了 P-糖蛋白介导的药物挤出。
• Synthesis and Characterization of Organolanthanide Complexes with a Calix[4]-pyrrolyl Ligand and Their Catalytic Activities toward Hydrophosphonylation of Aldehydes and Unactivated Ketones
  作者：Shuangliu Zhou、Hengyu Wang、Jian Ping、Shaowu Wang、Lijun Zhang、Xiancui Zhu、Yun Wei、Fenhua Wang、Zhijun Feng、Xiaoxia Gu、Song Yang、Hui Miao

  DOI：10.1021/om2008925

  日期：2012.3.12

  The alkali metal salt free dinuclear trivalent lanthanide amido complexes (eta(5):eta(1):eta(5):eta(1)-Et-8-calix[4]-pyrrolyl)LnN-(SiMe3)(2)}(2) (Ln = Nd (2), Sm (3), Gd (4)) were prepared through the silylamine elimination reactions of calix[4]-pyrrole [Et2C(C4H2NH)](4) (1) with 2 equiv of [(Me3Si)(2)N](3)Ln(mu-Cl)Li(THF)(3) (Ln = Nd, Sm, Gd) in toluene at 110 degrees C. The complexes were fully characterized by elemental, spectroscopic, and single-crystal X-ray analyses. Studies on the catalytic activity of the new lanthanide amido complexes revealed that these complexes can be used as efficient catalysts for hydrophosphonylation of aldehydes and unactivated ketones, affording the products in high yields by employing a low catalyst loading (0.1 mol %) at room temperature in a short time (20 min). Noteworthy is that it is the first application of calix[4]-pyrrolyl-supported lanthanide amides as catalysts to catalyze the hydrophosphonylation of aldehydes and unactivated ketones under mild conditions.
• Stabilization demands of diethyl phosphonate substituted carbocations as revealed by substituent effects
  作者：Xavier Creary、Ted L. Underiner

  DOI：10.1021/jo00212a033

  日期：1985.6