2-bromo-1-(2-methoxy-4,6-dimethylphenyl)ethanone | 136382-01-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-1-(2-methoxy-4,6-dimethylphenyl)ethanone
• 英文别名: 2-bromo-1-(2-methoxy-4,6-dimethylphenyl)ethan-1-one
• CAS: 136382-01-9
• 化学式: C₁₁H₁₃BrO₂
• 分子量: 257.127
• InChiKey: CBXARLPEXZEGOM-UHFFFAOYSA-N

物化性质

• 沸点：
  326.3±37.0 °C(Predicted)
• 密度：
  1.348±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  2-bromo-1-(2-methoxy-4,6-dimethylphenyl)ethanone 在 三乙胺 作用下， 以 丙酮 、 苯 为溶剂， 反应 24.0h， 生成 7-methoxy-5-methylindan-1-one
  参考文献：
  名称：

  The Power of Solvent in Altering the Course of Photorearrangements

  摘要：

  A clean bifurcation between two important photochemical reactions through competition of a triplet state Type II H-abstraction reaction with a photo-Favorskii rearrangement for (o/p)-hydroxy-o-methylphenacyl esters that depends on the water content of the solvent has been established. The switch from the anhydrous Type II pathway that yields indanones to the aqueous-dependent pathway producing benzoturanones occurs abruptly at low water concentrations (similar to 8%). The surprisingly clean yields suggest that such reactions are synthetically promising.

  DOI：

  10.1021/ol102887f
• 作为产物：
  描述：

  3,5-二甲基苯甲醚 在 zinc(II) oxide 、 copper(ll) bromide 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 2-bromo-1-(2-methoxy-4,6-dimethylphenyl)ethanone
  参考文献：
  名称：

  The Power of Solvent in Altering the Course of Photorearrangements

  摘要：

  A clean bifurcation between two important photochemical reactions through competition of a triplet state Type II H-abstraction reaction with a photo-Favorskii rearrangement for (o/p)-hydroxy-o-methylphenacyl esters that depends on the water content of the solvent has been established. The switch from the anhydrous Type II pathway that yields indanones to the aqueous-dependent pathway producing benzoturanones occurs abruptly at low water concentrations (similar to 8%). The surprisingly clean yields suggest that such reactions are synthetically promising.

  DOI：

  10.1021/ol102887f

文献信息

• SMALL MOLECULE MODIFIERS OF THE HEC1-NEK2 INTERACTION IN G2/M
  申请人：Lee Wen-Hwa

  公开号：US20150105391A1

  公开（公告）日：2015-04-16

  Certain embodiments of the present invention provide selected compounds having a molecular structure according to Formula 1: In Formula 1, Z is —CO—, —SO—, or —SO 2 —; Ar is phenyl, heteroaryl, or heterocycloalkyl; Het is heteroaryl; R is R″, X, or NR 1 R 2 ; R′ is R 3 , or OR 3 ; R″ is R 4 , or OR 4 ; R 1 and R 2 are each independently H, alkyl, or acyl; R 3 is H, heteroaryl, or alkyl; R 4 is H, heteroaryl, or C n H 2n+1 (n>2); and X is F, Br, I, CN, or NO 2 . In some embodiments, compounds having a molecular structure according to Formula 1 have the property of inhibiting a growth of a cell line selected from HeLa and MB468 with a sub-micromolar IC 50 .

  本发明的某些实施例提供具有分子结构的选择性化合物，符合以下公式1： 在公式1中，Z为—CO—，—SO—或—SO2—；Ar为苯基，杂环芳基或杂环烷基；Het为杂环芳基；R为R″，X或NR1R2；R′为R3或OR3；R″为R4或OR4；R1和R2各自独立地为H，烷基或酰基；R3为H，杂环芳基或烷基；R4为H，杂环芳基或CnH2n+1（n>2）；X为F，Br，I，CN或NO2。在某些实施例中，具有符合公式1的分子结构的化合物具有抑制来自HeLa和MB468中选定细胞系的生长的特性，其IC50为亚微摩尔。
• An Eight-State Molecular Sequential Switch Featuring a Dual Single-Bond Rotation Photoreaction
  作者：Aaron Gerwien、Benjamin Jehle、Marvin Irmler、Peter Mayer、Henry Dube

  DOI：10.1021/jacs.1c11183

  日期：2022.2.23

  switching function, and less precision and selectivity of switching events. Herein we present an approach for solving this essential problem with a different photoswitching concept. A basic molecular switch architecture provides precision photoswitching between eight different states via controlled rotations around three adjacent covalent bonds. All eight states can be populated one after another in an eight-step

  典型的光开关通过简单的异构化反应在两种不同状态之间相互转换，这代表了应用的基本限制。为了扩大开关容量，通常必须将不同的光电开关连接在一起，从而导致分子量大幅增加、开关功能降低以及开关事件的精度和选择性降低。在这里，我们提出了一种用不同的光开关概念解决这个基本问题的方法。基本的分子开关结构通过围绕三个相邻共价键的受控旋转提供八种不同状态之间的精确光转换。通过在光化学 Hula-Twist 异构化和热单键旋转之间交替，可以在八步循环中依次填充所有八种状态。通过简单地改变溶剂和温度，相同的开关也可以经历不同的循环，而不是在选择性序列中仅相互转换五种异构体。这种行为是通过发现前所未有的光反应（单光子双单键旋转）来实现的。
• Small molecule modifiers of the HEC1-NEK2 interaction in G2/M
  申请人：The Regents of the University of California

  公开号：US09422275B2

  公开（公告）日：2016-08-23

  Certain embodiments of the present invention provide selected compounds having a molecular structure according to Formula 1: In Formula 1, Z is —CO—, —SO—, or —SO2—; Ar is phenyl, heteroaryl, or heterocycloalkyl; Het is heteroaryl; R is R″, X, or NR1R2; R′ is R3, or OR3; R″ is R4, or OR4; R1 and R2 are each independently H, alkyl, or acyl; R3 is H, heteroaryl, or alkyl; R4 is H, heteroaryl, or CnH2n+1 (n>2); and X is F, Br, I, CN, or NO2. In some embodiments, compounds having a molecular structure according to Formula 1 have the property of inhibiting a growth of a cell line selected from HeLa and MB468 with a sub-micromolar IC50.

  本发明的某些实施例提供了具有分子结构式1的选择性化合物：在式1中，Z是—CO—，—SO—或—SO2—; Ar是苯基，杂环芳基或杂环烷基; Het是杂环芳基; R是R″，X或NR1R2; R'是R3或OR3; R″是R4或OR4; R1和R2各自独立地是H，烷基或酰基; R3是H，杂环芳基或烷基; R4是H，杂环芳基或CnH2n + 1（n> 2）; X是F，Br，I，CN或NO2。在某些实施例中，具有分子结构式1的化合物具有抑制从HeLa和MB468中选择的细胞系的生长的性质，其IC50为亚微米。
• Synthesis and Biological Evaluation of a Series of Novel Inhibitor of Nek2/Hec1 Analogues
  作者：Xiao-Long Qiu、Guideng Li、Guikai Wu、Jiewen Zhu、Longen Zhou、Phang-Lang Chen、A. Richard Chamberlin、Wen-Hwa Lee

  DOI：10.1021/jm8015969

  日期：2009.3.26

  High expression in cancer 1 (Hec1) is an oncogene overly expressed in many human cancers. Small molecule inhibitor of Nek2/Hcc1 (INH) targeting the Heel and its regulator, Nek2, in the mitotic pathway, was identified to inactivate Hec1/Nek2 function mediated by protein degradation that subsequently leads to chromosome mis-segregation and cell death. To further improve the efficacy of INH, a series of INH analogues were designed, synthesized, and evaluated. Among these 33 newly synthesized analogues, three of them, 6, 13, and 21, have 6-8 fold more potent cell killing activity than the previous lead compound INH1. Compounds 6 and 21 were chosen for analyzing the underlying action mechanism. They target directly the Hec1/Nek2 pathway and cause chromosome mis-alignment as well as cell death, a mechanism similar to that of INH1, This initial exploration of structural/functional relationship of INH may advance the progress for developing clinically applicable INH analogue.
• US9422275B2
  申请人：——

  公开号：US9422275B2

  公开（公告）日：2016-08-23