5,5-diphenyl-valeric acid methyl ester | 109250-45-5

• 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: 5,5-diphenyl-valeric acid methyl ester
• 英文别名: 5,5-Diphenyl-valeriansaeure-methylester；Methyl 5,5-diphenylpentanoate
• CAS: 109250-45-5
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: QOAMFLIVOMJSGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,5-diphenyl-valeric acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 5,5-二苯基-1-戊醇
  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：

  3,3-二苯基丙醇 在 氢氧化钾 、 硫酸 、 sodium 、 三乙胺 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 49.0h， 生成 5,5-diphenyl-valeric acid methyl ester
  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

• Electrophotocatalytic diamination of vicinal C–H bonds
  作者：Tao Shen、Tristan H. Lambert

  DOI：10.1126/science.abf2798

  日期：2021.2.5

  carbon-hydrogen (C–H) bonds to carbon–nitrogen (C–N) bonds is a highly valued transformation. Existing strategies typically accomplish such reactions at only a single C–H site because the first derivatization diminishes the reactivity of surrounding C–H bonds. Here, we show that alkylated arenes can undergo vicinal C–H diamination reactions to form 1,2-diamine derivatives through an electrophotocatalytic strategy

  未活化的碳氢键（C–H）转换为碳氮键（C–N）是非常有价值的转化。现有的策略通常仅在单个CH位置完成此类反应，因为第一次衍生化会降低周围CH键的反应性。在这里，我们表明烷基化的芳烃可以通过邻位的CH氨化反应，通过电光催化策略使用乙腈作为溶剂和氮源，形成1,2-二胺衍生物。该反应由三氨基环丙烯（TAC）离子催化，该离子经过阳极氧化以提供稳定的自由基指示，而阴极反应则将质子还原为分子氢。用白光紧凑型荧光灯照射TAC自由基指示剂（最大吸收波长为450至550纳米）会产生强烈氧化的光激发中间体。取决于所使用的电解质，可获得3，4-二氢咪唑或氮丙啶产物。
• Reduction of activated thiopyridyl compounds by zinc metal
  作者：Jean Boivin、Jean-Yves Lallemand、Andreas Schmitt、Samir Z. Zard

  DOI：10.1016/0040-4039(95)01497-6

  日期：1995.10

  Starting from thiopyridyl compounds bearing a radical stabilizing group in α-position to the thiopyridyl moiety, the thiopyridyl group can be easily removed upon reduction by zinc metal in acetic acid.

  从在硫代吡啶基部分的α位带有自由基稳定基团的硫代吡啶基化合物开始，通过在乙酸中用锌金属还原，可以很容易地除去硫代吡啶基。
• Ｓ１Ｐ３受容体拮抗薬
  申请人：トーアエイヨー株式会社

  公开号：JP2005247691A

  公开（公告）日：2005-09-15

  PROBLEM TO BE SOLVED: To obtain a compound having selective SIP3 receptor antagonism and a medicine containing the same.

  SOLUTION: The medicine comprises an aminopropionic acid derivative represented by general formula (1) (R1is a hydrogen atom or a lower alkyl group; R2is formula A; A is CO or CH2; E is an oxygen atom or an NR4; R3is a lower alkyl group or formula B; G is CH, a nitrogen atom or a phosphorus atom; J is an oxygen atom or a sulfur atom; R4is a hydrogen atom or a lower alkyl group; R5, R6and R7are each the same or different and a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, a nitro group or a haloalkyl group; m is an integer of 1-8; n is an integer of 1-5) or its pharmaceutically permissible salt as an active ingredient.

  COPYRIGHT: (C)2005,JPO&NCIPI

  需要解决的问题：获得具有选择性SIP3受体拮抗作用的化合物和含有该化合物的药物。 解决方案：所述药物包含一种由通式（1）表示的氨基丙酸衍生物（其中R1为氢原子或较低的烷基；R2为公式A；A为CO或CH2；E为氧原子或NR4；R3为较低的烷基或公式B；G为CH、氮原子或磷原子；J为氧原子或硫原子；R4为氢原子或较低的烷基；R5、R6和R7分别相同或不同，为氢原子、较低的烷基、较低的烷氧基、卤素原子、硝基或卤代烷基；m为1-8的整数；n为1-5的整数），或其药学上可接受的盐作为活性成分。 版权所有：（C）2005，JPO&NCIPI
• The Reformatsky Reaction in Syntheses of ι,ι-Diarylalkanoic Acids and Related Compounds^1,2
  作者：L. H. KLEMM、G. M. BOWER

  DOI：10.1021/jo01097a006

  日期：1958.3
• New 1,3-dioxolane and 1,3-dioxane derivatives as effective modulators to overcome multidrug resistance
  作者：Matthias Schmidt、Johannes Ungvári、Julia Glöde、Bodo Dobner、Andreas Langner

  DOI：10.1016/j.bmc.2007.01.024

  日期：2007.3

  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.