(1R,2S)-1,2-bis-(2-chloro-phenyl)-ethane-1,2-diol | 71776-58-4

• 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: (1R,2S)-1,2-bis-(2-chloro-phenyl)-ethane-1,2-diol
• 英文别名: 1,2-bis(2-chlorophenyl)ethane-1,2-diol；1,2-di(2-chlorophenyl)ethane-1,2-diol；1,2-bis(2-chlorophenyl)-1,2-ethanediol；(1R,2S)-1,2-bis(2-chlorophenyl)ethane-1,2-diol
• CAS: 71776-58-4
• 化学式: C₁₄H₁₂Cl₂O₂
• 分子量: 283.154
• InChiKey: PRPZPQDFVUBHDN-OKILXGFUSA-N

物化性质

• 沸点：
  422.9±40.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S)-1,2-bis-(2-chloro-phenyl)-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[2-chlorophenyl]-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：

  2-氯甲苯 在 sodium hydroxide 、 溴 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 (1R,2S)-1,2-bis-(2-chloro-phenyl)-ethane-1,2-diol
  参考文献：
  名称：

  醇类的光化学反应-II：芳族醇的辐照

  摘要：

  芳香醇的紫外线照射导致形成多种产物：羰基化合物，醚，α-乙二醇和四-芳基-1,4-二恶烷。

  DOI：

  10.1016/0040-4020(82)85088-6

文献信息

• The influencing factors and marketing strategies of developing telecommunication industry customer loyalty
  作者：Li Li、Wengui Su、Jian Jiang

  DOI：10.1145/1089551.1089697

  日期：——

  In this paper, we analyze the influencing factors of the customer loyalty and set up the relational assess model, then apply analytic hierarchy process to establish the relation weights which influence the customer loyalty. At last, by means of applied instances in telecommunication industry, we represent the internal relations between the influencing factor weights and the customer loyalty and put forward marketing strategies on product and customer divergences to develop the customer loyalty.

  本文中，我们分析了客户忠诚度的影响因素，并构建了关系评估模型，随后应用层次分析法确立了影响客户忠诚度的各因素权重关系。最后，通过电信行业的应用实例，展示了影响因素权重与客户忠诚度之间的内在联系，并针对产品和客户分化的差异，提出了相应的营销策略以提升客户忠诚度。
• Chiral Phosphoric Acid Directed Regioselective Acetalization of Carbohydrate-Derived 1,2-Diols
  作者：Enoch Mensah、Nicole Camasso、Will Kaplan、Pavel Nagorny

  DOI：10.1002/anie.201304298

  日期：2013.12.2

  In control: A chiral phosphoric acid catalyst (see scheme) significantly enhances or completely overrides the inherent regioselective acetalization profiles exhibited by monosaccharide‐derived 1,2‐diol substrates. This study represents the first example of chiral‐catalyst‐directed regio‐ and enantioselective intermolecular acetalizations, which are complementary to existing methods for substrate‐controlled

  对照：手性磷酸催化剂（参见方案）显着增强或完全超越了由单糖衍生的1,2-二醇底物表现出的固有的区域选择性缩醛化特性。这项研究代表了手性催化剂指导的区域和对映选择性分子间缩醛化的第一个例子，这是对现有的多元醇底物控制功能化方法的补充。
• 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。
• Application of coumarin dyes for organic photoredox catalysis
  作者：Andrea Gualandi、Giacomo Rodeghiero、Emanuele Della Rocca、Francesco Bertoni、Marianna Marchini、Rossana Perciaccante、Thomas Paul Jansen、Paola Ceroni、Pier Giorgio Cozzi

  DOI：10.1039/c8cc04048f

  日期：——

  Here we report the application of readily prepared and available coumarin dyes for photoredox catalysis, which are able to mimic powerful reductant [Ir(III)] complexes. Coumarin derivatives 9 and 10 were employed as photoreductants in pinacol coupling and in other reactions, in the presence of Et3N as a sacrificial reducing agent. As the electronic, photophysical, and steric properties of coumarins

  在这里，我们报告易于制备和可用的香豆素染料在光氧化还原催化中的应用，它们能够模拟强大的还原剂[Ir（III）]配合物。在Et 3 N作为牺牲还原剂的情况下，香豆素衍生物9和10在频哪醇偶联和其他反应中用作光还原剂。由于香豆素的电子，光物理和空间性质可以改变，因此可以预测对几类光氧化还原反应的广泛适用性。
• Influence of External Ligands and Auxiliaries on the Reactivity of Low-Valent Titanium in McMurry Reaction:  Selectivity and Mechanistic Profile
  作者：N. Balu、S. K. Nayak、A. Banerji

  DOI：10.1021/ja9535221

  日期：1996.1.1

  auxiliaries also resisted deoxygenation completely to give the pinacols in higher yields and better diastereoselectivity, as compared to pyridine-modified LVT system. Amongst these modified reagents, the LVT−catechol (1:1) system was found to be the most efficient combination for total pinacolization of aromatic carbonyl compounds, even under refluxing conditions. The actual titanium reagent responsible

  已经探索了各种外部配体/助剂对低价钛 (LVT) 试剂 (McMurry 偶联) 介导的还原羰基偶联反应的影响。从 Tyrlik 的 TiCl3-Mg-THF 系统产生的 LVT 物质已被选择用于反应性调整试验。我们的研究表明，将大约 10 当量的吡啶（一种 π 受体配体）与 TiCl3 结合到 THF 溶剂化 LVT 试剂中可以阻止苯乙酮在中间频哪醇阶段的还原二聚化。与吡啶修饰的 LVT 系统相比，通过共价结合的单羟基、1,2-和 1,3-二羟基助剂对 LVT 种类的调节也完全抵抗脱氧，从而以更高的产率和更好的非对映选择性得到频哪醇。在这些改性试剂中，LVT-邻苯二酚 (1: 1) 系统被发现是芳香羰基化合物总频哪醇化的最有效组合，即使在回流条件下也是如此。实际负责的钛试剂...