1,2-bis(4-fluorophenyl)ethane-1,2-diol | 119441-83-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2-bis(4-fluorophenyl)ethane-1,2-diol
• 英文别名: 1,2-bis(4-fluorophenyl)-1,2-ethanediol；(1R,2S)-1,2-bis(4-fluorophenyl)ethane-1,2-diol
• CAS: 119441-83-7
• 化学式: C₁₄H₁₂F₂O₂
• 分子量: 250.245
• InChiKey: DDHFZTKNJGJNLK-OKILXGFUSA-N

物化性质

• 沸点：
  374.9±37.0 °C(Predicted)
• 密度：
  1.331±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-bis(4-fluorophenyl)ethane-1,2-diol 在 盐酸 作用下， 以 氯仿 为溶剂， 反应 8.0h， 生成 (cis/cis)-1-{3-[4-(4,5-bis[4-fluorophenyl]-1,4-dioxolan-2-yl)phenoxy]propyl}-4-methylpiperazine
  参考文献：
  名称：

  New 1,3-dioxolane and 1,3-dioxane derivatives as effective modulators to overcome multidrug resistance

  摘要：

  Multidrug resistance (MDR) to antitumor agents represents a major obstacle to a successful chemotherapy of cancer. Overexpression of P-glycoprotein (p-gp) seems to be the major factor responsible for MDR. A large number of chemically unrelated compounds are known to interact with p-gp resulting in a decreasing resistance. In our efforts related to structure-activity studies of new potential MDR reversal agents we synthesized a series of compounds that differ in the aromatic core structure, the linker, and the basic moiety. For our search of new aromatic core structures we synthesized novel 2,2-diphenyl-1,3-dioxolane, 2,2- diphenyl-1,3-dioxane, and 4,5-diphenyl-1,3-dioxolane derivatives. A range of lipophilic linker structures and protonable basic moieties were synthesized and investigated to optimize the structure of the potential MDR-modulators. The compounds were tested in vitro using human Caco-2 cells. Both the cytotoxicity of the synthons and their ability to resensitize the cells were determined with a MTT assay. The results show that at low concentration various substances reverse tumor cell MDR. Some of the new structures show better effects than established modulators like trifluoperazine. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.024
• 作为产物：
  描述：

  4,4'-二氟安息香 在 sodium tetrahydroborate 作用下， 以 异丙醇 为溶剂， 反应 12.0h， 以83%的产率得到1,2-bis(4-fluorophenyl)ethane-1,2-diol
  参考文献：
  名称：

  New 1,3-dioxolane and 1,3-dioxane derivatives as effective modulators to overcome multidrug resistance

  摘要：

  Multidrug resistance (MDR) to antitumor agents represents a major obstacle to a successful chemotherapy of cancer. Overexpression of P-glycoprotein (p-gp) seems to be the major factor responsible for MDR. A large number of chemically unrelated compounds are known to interact with p-gp resulting in a decreasing resistance. In our efforts related to structure-activity studies of new potential MDR reversal agents we synthesized a series of compounds that differ in the aromatic core structure, the linker, and the basic moiety. For our search of new aromatic core structures we synthesized novel 2,2-diphenyl-1,3-dioxolane, 2,2- diphenyl-1,3-dioxane, and 4,5-diphenyl-1,3-dioxolane derivatives. A range of lipophilic linker structures and protonable basic moieties were synthesized and investigated to optimize the structure of the potential MDR-modulators. The compounds were tested in vitro using human Caco-2 cells. Both the cytotoxicity of the synthons and their ability to resensitize the cells were determined with a MTT assay. The results show that at low concentration various substances reverse tumor cell MDR. Some of the new structures show better effects than established modulators like trifluoperazine. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.024

文献信息

• CBZ6 as a Recyclable Organic Photoreductant for Pinacol Coupling
  作者：Hua Wang、Jian-Ping Qu、Yan-Biao Kang

  DOI：10.1021/acs.orglett.1c00537

  日期：2021.4.16

  % CBZ6)-catalyzed reductive (pinacol) coupling of aldehydes, ketones, and imines has been developed. Irradiated by purple light (407 nm) using triethylamine as an electron donor, a variety of 1,2-diols and 1,2-diamines could be prepared. The oxidation potential of the excited state of CBZ6 is established as −1.92 V (vs saturated calomel electrode (SCE)). The relative high reductive potential enables

  已经开发了可回收的有机光还原剂（1摩尔％CBZ6）催化的醛，酮和亚胺的还原（频哪醇）偶联。使用三乙胺作为电子供体，在紫色光（407 nm）照射下，可以制备各种1,2-二醇和1,2-二胺。CBZ6的激发态的氧化电位为-1.92 V（相对于饱和甘汞电极（SCE））。较高的还原电位使得羰基化合物及其衍生物能够还原偶联。CBZ6可以克量制备，并且对酸/碱或空气稳定。可用于大规模光还原合成，反应后高收率回收。
• Pinacolic Coupling of Aromatic Carbonyl Compounds Using Zn Powder in Aqueous Basic Media without Organic Solvents
  作者：Takehito Tsukinoki、Takatoshi Kawaji、Iwao Hashimoto、Shuntaro Mataka、Masashi Tashiro

  DOI：10.1246/cl.1997.235

  日期：1997.3

  Treatment of aromatic carbonyl compounds with Zn powder in 10% aq NaOH solution without using any organic solvents under the mild conditions afforded the corresponding 1,2-diols in good yields.

  在温和条件下，在不使用任何有机溶剂的情况下，用 Zn 粉末在 10% NaOH 水溶液中处理芳香族羰基化合物，以良好的收率得到相应的 1,2-二醇。
• An imidazolium-modified chiral rhodium/diamine-functionalized periodic mesoporous organosilica for asymmetric transfer hydrogenation of α-haloketones and benzils in aqueous medium
  作者：Feng Zhou、Xiaoying Hu、Ming Gao、Tanyu Cheng、Guohua Liu

  DOI：10.1039/c6gc01589a

  日期：——

  Use of a hydrophobic, imidazolium-functionalized periodic mesoporous organosilica for immobilizations of chiral organometallic complexes as a heterogeneous catalyst is a highly desirable as this catalyst can promote greatly an aqueous...

  非常需要使用疏水的，咪唑鎓官能化的周期性介孔有机二氧化硅作为非均相催化剂来固定手性有机金属配合物，因为该催化剂可以大大促进水性...
• The scalable pinacol coupling reaction utilizing the inorganic electride [Ca₂N]⁺·e⁻ as an electron donor
  作者：Ye Ji Kim、Sun Min Kim、Hideo Hosono、Jung Woon Yang、Sung Wng Kim

  DOI：10.1039/c4cc00802b

  日期：——

  An inorganic electride [Ca₂N]⁺·e⁻ is used as an efficient electron donor for the scalable pinacol coupling reaction with a high yield.

  一种无机电子亚胺[Ca₂N]⁺·e⁻被用作可扩展的高产率品可醇偶联反应的高效电子给体。
• Truly Catalytic and Enantioselective Pinacol Coupling of Aryl Aldehydes Mediated by Chiral Ti(III) Complexes^†
  作者：A. Chatterjee、T. H. Bennur、N. N. Joshi

  DOI：10.1021/jo0342875

  日期：2003.7.1

  A variety of chiral Ti(IV) complexes were reduced in situ with zinc in acetonitrile. The resulting chiral Ti(III) complexes were found to catalyze the pinacol coupling reaction stereoselectively. The best results were obtained from the Ti-SALEN complex, which was found to be an efficient catalyst at 10 mol % concentration. Various aromatic aldehydes were coupled to obtain chiral hydrobenzoin derivatives

  各种手性Ti（IV）配合物在乙腈中用锌原位还原。发现所得的手性Ti（III）配合物立体选择性地催化频哪醇偶联反应。从Ti-SALEN配合物获得了最佳结果，该配合物被发现是浓度为10 mol％的有效催化剂。偶联各种芳族醛以获得具有高非对映选择性和对映选择性的手性氢安息香衍生物。提出了合理的机制，使反应的立体化学结果合理化。