4-(3,4-dimethoxyphenyl)-1-phenylbutan-1-one | 221158-41-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(3,4-dimethoxyphenyl)-1-phenylbutan-1-one
• CAS: 221158-41-4
• 化学式: C₁₈H₂₀O₃
• 分子量: 284.355
• InChiKey: JPJSERGOZISOQK-UHFFFAOYSA-N

物化性质

• 沸点：
  426.4±35.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3,4-dimethoxyphenyl)-1-phenylbutan-1-one 在 三乙基硅烷 、 三氟乙酸 作用下， 反应 2.5h， 以90%的产率得到6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Inhibition of IGF-1R and lipoxygenase by nordihydroguaiaretic acid (NDGA) analogs

  摘要：

  Herein, we pursue the hypothesis that the structure of nordihydroguaiaretic acid (NDGA) can be refined for selective potency against the insulin-like growth factor 1 receptor (IGF-1R) as a potential therapeutic target for breast cancer while diminishing its action against other cellular targets. Thus, a set of NDGA analogs (7a-7h) was prepared and examined for inhibitory potency against IGF-1R kinase and an alternative target, 15-lipoxygenase (15 LOX). The anti-cancer effects of these compounds were determined by their ability to inhibit IGF-1 mediated cell growth of MCF-7 breast cancer cells. The design of the analogs was based upon a cursory Topliss approach in which one of NDGA's aromatic rings was modified with various substituents. Structural modification of one of the two catechol rings of NDGA was found to have little effect upon the inhibitory potency against both kinase activity of the IGF-1R and IGF-1 mediated cell growth of MCF-7 cells. 15-LOX was found to be most sensitive to structural modifications of NDGA. From the limited series of NDGA analogs examined, the compound that exhibited the greatest selectivity for IGF-1 mediated growth compared to 15-LOX inhibition was a cyclic analog 7h with a framework similar to a natural product isolated from Larrea divaricata. The results for 7h are significant because while NDGA displays biological promiscuity, 7h exhibits greater specificity toward the breast cancer target IGF-IR with that added benefit of possessing a 10-fold weaker potency against 15-LOX, an enzyme which has a purported tumor suppressing role in breast cancer. With increased specificity and potency, 7h may serve as a new lead in developing novel therapeutic agents for breast cancer. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.092
• 作为产物：
  描述：

  4-(3,4-二甲氧苯基)丁酸 在 lithium aluminium tetrahydride 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 4-(3,4-dimethoxyphenyl)-1-phenylbutan-1-one
  参考文献：
  名称：

  Inhibition of IGF-1R and lipoxygenase by nordihydroguaiaretic acid (NDGA) analogs

  摘要：

  Herein, we pursue the hypothesis that the structure of nordihydroguaiaretic acid (NDGA) can be refined for selective potency against the insulin-like growth factor 1 receptor (IGF-1R) as a potential therapeutic target for breast cancer while diminishing its action against other cellular targets. Thus, a set of NDGA analogs (7a-7h) was prepared and examined for inhibitory potency against IGF-1R kinase and an alternative target, 15-lipoxygenase (15 LOX). The anti-cancer effects of these compounds were determined by their ability to inhibit IGF-1 mediated cell growth of MCF-7 breast cancer cells. The design of the analogs was based upon a cursory Topliss approach in which one of NDGA's aromatic rings was modified with various substituents. Structural modification of one of the two catechol rings of NDGA was found to have little effect upon the inhibitory potency against both kinase activity of the IGF-1R and IGF-1 mediated cell growth of MCF-7 cells. 15-LOX was found to be most sensitive to structural modifications of NDGA. From the limited series of NDGA analogs examined, the compound that exhibited the greatest selectivity for IGF-1 mediated growth compared to 15-LOX inhibition was a cyclic analog 7h with a framework similar to a natural product isolated from Larrea divaricata. The results for 7h are significant because while NDGA displays biological promiscuity, 7h exhibits greater specificity toward the breast cancer target IGF-IR with that added benefit of possessing a 10-fold weaker potency against 15-LOX, an enzyme which has a purported tumor suppressing role in breast cancer. With increased specificity and potency, 7h may serve as a new lead in developing novel therapeutic agents for breast cancer. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.092

文献信息

• Ni-Catalyzed β-Alkylation of Cyclopropanol-Derived Homoenolates
  作者：L. Reginald Mills、Cuihan Zhou、Emily Fung、Sophie A. L. Rousseaux

  DOI：10.1021/acs.orglett.9b03435

  日期：2019.11.1

  Metal homoenolates are valuable synthetic intermediates which provide access to β-functionalized ketones. In this report, we disclose a Ni-catalyzed β-alkylation reaction of cyclopropanol-derived homoenolates using redox-active N-hydroxyphthalimide (NHPI) esters as the alkylating reagents. The reaction is compatible with 1°, 2°, and 3° NHPI esters. Mechanistic studies imply radical activation of the

  金属均烯酸酯是有价值的合成中间体，可提供获得β-官能化酮的途径。在此报告中，我们公开了使用氧化还原活性N-羟基邻苯二甲酰亚胺（NHPI）酯作为烷基化试剂的镍催化的环丙醇衍生的均烯酸酯的β-烷基化反应。该反应与1°，2°和3°NHPI酯相容。机理研究表明，在环丙醇上会发生NHPI酯的自由基活化和2eβ-碳的消除。
• Copper‐Catalyzed Cross‐Coupling of Acylzirconocenes and Diaryliodonium Salts: An Efficient Synthesis of Alkyl‐aryl‐ketones from Alkenes
  作者：Simone Grosso、Marcelina Mlynczak、Gwilherm Evano、Olivier Riant

  DOI：10.1002/ejoc.202300938

  日期：2023.12.13

  An efficient cross-coupling between acylzirconocenes, readily prepared by hydrozirconation/carbonylation of alkenes, and diaryliodonium tetrafluoroborates is reported. This procedure enables the synthesis of a variety of alkyl-aryl-ketones upon simple catalysis with copper cyanide without the need of additional ligands and only requires a low pressure of carbon monoxide generated in situ, in a two-chamber

  据报道，通过烯烃的氢化锆化/羰基化容易制备的酰基锆茂和四氟硼酸二芳基碘之间的有效交叉偶联。该方法能够在氰化铜的简单催化下合成各种烷基芳基酮，无需额外的配体，并且仅需要在两室反应器中由 N-甲酰糖精原位产生低压一氧化碳。
• Inhibition of IGF-1R and lipoxygenase by nordihydroguaiaretic acid (NDGA) analogs
  作者：Joseph E. Blecha、Marc O. Anderson、Jennifer M. Chow、Christle C. Guevarra、Celia Pender、Cristina Penaranda、Marianna Zavodovskaya、Jack F. Youngren、Clifford E. Berkman

  DOI：10.1016/j.bmcl.2007.04.092

  日期：2007.7

  Herein, we pursue the hypothesis that the structure of nordihydroguaiaretic acid (NDGA) can be refined for selective potency against the insulin-like growth factor 1 receptor (IGF-1R) as a potential therapeutic target for breast cancer while diminishing its action against other cellular targets. Thus, a set of NDGA analogs (7a-7h) was prepared and examined for inhibitory potency against IGF-1R kinase and an alternative target, 15-lipoxygenase (15 LOX). The anti-cancer effects of these compounds were determined by their ability to inhibit IGF-1 mediated cell growth of MCF-7 breast cancer cells. The design of the analogs was based upon a cursory Topliss approach in which one of NDGA's aromatic rings was modified with various substituents. Structural modification of one of the two catechol rings of NDGA was found to have little effect upon the inhibitory potency against both kinase activity of the IGF-1R and IGF-1 mediated cell growth of MCF-7 cells. 15-LOX was found to be most sensitive to structural modifications of NDGA. From the limited series of NDGA analogs examined, the compound that exhibited the greatest selectivity for IGF-1 mediated growth compared to 15-LOX inhibition was a cyclic analog 7h with a framework similar to a natural product isolated from Larrea divaricata. The results for 7h are significant because while NDGA displays biological promiscuity, 7h exhibits greater specificity toward the breast cancer target IGF-IR with that added benefit of possessing a 10-fold weaker potency against 15-LOX, an enzyme which has a purported tumor suppressing role in breast cancer. With increased specificity and potency, 7h may serve as a new lead in developing novel therapeutic agents for breast cancer. (C) 2007 Elsevier Ltd. All rights reserved.