diethyl 3,5-bis(trifluoromethyl)benzyl phosphonate | 125138-12-7

• 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 3,5-bis(trifluoromethyl)benzyl phosphonate
• 英文别名: Diethyl {[3,5-bis(trifluoromethyl)phenyl]methyl}phosphonate；1-(diethoxyphosphorylmethyl)-3,5-bis(trifluoromethyl)benzene
• CAS: 125138-12-7
• 化学式: C₁₃H₁₅F₆O₃P
• 分子量: 364.224
• InChiKey: YAVRWCHSQKIQDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  diethyl 3,5-bis(trifluoromethyl)benzyl phosphonate 以 盐酸 、 乙醇 为溶剂， 反应 72.0h， 以to give 0.41 g of the product (49% yield) the as a white solid的产率得到3,5-Bis(trifluoromethyl)benzylphosphonic acid
  参考文献：
  名称：

  Trifluoromethylbenzylphosphonates useful in treating osteoporosis

  摘要：

  本发明揭示了一种一般式I的新型苄基膦酸酯化合物：##STR1## 作为治疗骨质疏松症等骨质疾病，包括绝经后骨质疏松症，能够增加哺乳动物骨骼形成和骨质量。

  公开号：

  US05300687A1
• 作为产物：
  描述：

  3,5-双三氟甲基苄基溴 在 亚磷酸三乙酯 作用下， 以48%的产率得到diethyl 3,5-bis(trifluoromethyl)benzyl phosphonate
  参考文献：
  名称：

  Trifluoromethybenzylphosphonates useful in treating osteoporosis

  摘要：

  揭示了一种通式I的新型苄基膦酸酯化合物，可用于治疗骨质疏松症等骨质流失疾病，包括更年期后骨质疏松症，在哺乳动物中增加骨形成和骨量。

  公开号：

  US05532226A1

文献信息

• Trifluoromethylbenzylphosphonates useful in treating osteoporosis
  申请人：Ortho Pharmaceutical Corporation

  公开号：US05300687A1

  公开（公告）日：1994-04-05

  Novel benzylphosphonate compounds of the general formula I: ##STR1## are disclosed as useful in treating bone wasting diseases including postmenopausal osteoporosis in increasing in mammals bone formation and bone mass.

  公开了一种通式为I的新型苄基膦酸酯化合物，用于治疗骨质疏松症等骨质流失疾病，包括增加哺乳动物骨骼形成和骨量的绝经后骨质疏松症。
• Systematic study of a series of highly fluorescent rod-shaped donor-acceptor systems
  作者：R. M. Hermant、N. A. C. Bakker、T. Scherer、B. Krijnen、Jan W. Verhoeven

  DOI：10.1021/ja00159a050

  日期：1990.1

  The synthesis and emissive properties of bichromophoric molecules are reported. All systems contain an anilino group as a one-electron donor (D) and various substituted ethylene moieties as electron acceptor (A) separated by a rod-shaped alicyclic framework provide by a piperidine ring. From the emissive properties it is concluded that in these molecules the electronic coupling between D and A is sufficient

  报道了双发色分子的合成和发射特性。所有系统都包含一个苯胺基作为单电子供体 (D) 和各种取代的亚乙基部分作为电子受体 (A)，它们被由哌啶环提供的棒状脂环骨架隔开。从发射特性可以得出结论，在这些分子中，D 和 A 之间的电子耦合足以在激发时允许完全电荷转移（如果热力学可行）
• Total Syntheses of the Isomeric Aglain Natural Products Foveoglin A and Perviridisin B: Selective Excited‐State Intramolecular Proton‐Transfer Photocycloaddition
  作者：Wenyu Wang、Anthony Clay、Retheesh Krishnan、Neil J. Lajkiewicz、Lauren E. Brown、Jayaraman Sivaguru、John A. Porco

  DOI：10.1002/anie.201707539

  日期：2017.11.13

  intramolecular proton‐transfer (ESIPT) photocycloaddition of 3‐hydroxyflavones with trans, trans‐1,4‐diphenyl‐1,3‐butadiene is described. Using this methodology, total syntheses of the natural products (±)‐foveoglin A and (±)‐perviridisin B were accomplished. Enantioselective ESIPT photocycloaddition using TADDOLs as chiral hydrogen‐bonding additives provided access to (+)‐foveoglin A. Mechanistic studies

  描述了3-羟基黄酮与反式，反式-1,4-二苯基-1,3-丁二烯的选择性激发态分子内质子转移（ESIPT）光环加成反应。利用该方法，完成了天然产物(±)-foveoglin A和(±)-perviridisin B的全合成。使用 TADDOL 作为手性氢键添加剂的对映选择性 ESIPT 光环加成反应提供了 (+)-foveoglin A 的途径。机理研究揭示了光诱导电子转移 (PET) 途径的可能性。
• Photoinduced Charge Separation in Rigid Bichromophoric Compounds and Charge Transfer State Electron Transfer Reactivity
  作者：J. L. Habib Jiwan、J. Ph. Soumillion

  DOI：10.1021/j100039a007

  日期：1995.9

  Bichromophoric compounds giving, after photoexcitation, a locally excited state (LE) rapidly followed by an intramolecular charge transfer (CT) state were designed using a Paddon-Row type synthesis. The electron-accepting end of the CT state is chosen in order to play the role of an electron relay versus external accepters. In this way, electron transfer photosensitization is made available by using the CT state of bichromophores. The photophysics of the synthesized bichromophores is discussed; and the reductive dechlorination of polychlorinated benzenes is used as a test reaction. The bichromophoric sensitizer is unexpectedly found to be totally regenerated: the reaction is shown to be initiated by an electron transfer from the CT state to the chlorinated quencher. A rapidly breaking radical anion leads to the dechlorination, while the recombination of the sensitizer radical cation with the released chloride anion opens the way to the sensitizer recovery.
• Trifluoromethyl Groups in Crystal Design of 1,4-Diphenyl-1,3-butadienes for Topochemical [2 + 2] Photodimerization
  作者：Jin Liu、Natalie L. Wendt、Kelly J. Boarman

  DOI：10.1021/ol0475111

  日期：2005.3.1

  UV irradiation of the powdered crystalline sample of each of three (EE)-1,4-di(trifluoromethyl-substituted)phenyl-1,3-butadienes (1-3) was found to yield a single [2 + 2] cycloaddition product in the solid state. Moreover, upon irradiation, the crystalline samples of two (EE)-1,4-di(trifluoromethyl- and fluorine-substituted)phenyl-1,3-butadienes (4, 5) undergo a similar conversion to afford a [2 + 2] cycloaddition product, respectively. Our observations suggest that trifluoromethyl groups can be used to direct 1,4-diphenyl-1,3-butadiene molecules to form a parallel, offset-stacked orientation suitable for topochemical [2 + 2] cycloaddition.