2-methyl-2-(2-methylphenyl)propionaldehyde | 127106-02-9

• 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: 2-methyl-2-(2-methylphenyl)propionaldehyde
• 英文别名: 2-(2-methylphenyl)-2-methylpropanal；2-Methyl-2-(o-tolyl)propanal；2-methyl-2-(2-methylphenyl)propanal
• CAS: 127106-02-9
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: VHAZKKKEUDNFJE-UHFFFAOYSA-N

物化性质

• 沸点：
  239.3±9.0 °C(Predicted)
• 密度：
  0.955±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methyl-2-(2-methylphenyl)propionaldehyde 在 lithium hydroxide 、 双氧水 作用下， 以 水 、 乙腈 为溶剂， 生成 tert-butyl N-[1-amino-3-methyl-3-(2-methylphenyl)-1-oxobutan-2-yl]-N-methylcarbamate
  参考文献：
  名称：

  Synthesis and activity of novel analogs of hemiasterlin as inhibitors of tubulin polymerization: modification of the A segment

  摘要：

  Analogs of hemiasterlin (1) and HTI-286 (2), which contain various aromatic rings in the A segment, were synthesized as potential inhibitors of tubulin polymerization. The structure-activity relationships related to stereo- and regio-chemical effects of substituents on the aromatic ring in the A segment were studied. Analogs, which carry a meta-substituted phenyl ring in the A segment show comparable activity for inhibition of tubulin polymerization to 2, as well as in the cell proliferation assay using KB cells containing P-glycoprotein, compared to those of 1 and 2. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.024
• 作为产物：
  描述：

  2-甲基苯甲醛 在 三(五氟苯基)硼烷 、 lithium diisopropyl amide 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 苯 为溶剂， 反应 15.0h， 生成 2-methyl-2-(2-methylphenyl)propionaldehyde
  参考文献：
  名称：

  Synthesis and activity of novel analogs of hemiasterlin as inhibitors of tubulin polymerization: modification of the A segment

  摘要：

  Analogs of hemiasterlin (1) and HTI-286 (2), which contain various aromatic rings in the A segment, were synthesized as potential inhibitors of tubulin polymerization. The structure-activity relationships related to stereo- and regio-chemical effects of substituents on the aromatic ring in the A segment were studied. Analogs, which carry a meta-substituted phenyl ring in the A segment show comparable activity for inhibition of tubulin polymerization to 2, as well as in the cell proliferation assay using KB cells containing P-glycoprotein, compared to those of 1 and 2. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.024

文献信息

• Rhodium(I)-Catalyzed Cycloisomerization of Benzylallene-Alkynes through CH Activation
  作者：Yasuaki Kawaguchi、Shigeo Yasuda、Akira Kaneko、Yuki Oura、Chisato Mukai

  DOI：10.1002/anie.201403990

  日期：2014.7.14

  RhI‐catalyzed cycloisomerization of benzylallene‐alkynes produced the tricyclo[9.4.0.03,8]pentadecapentaene skeleton through a CH bond activation in good yields. A plausible reaction mechanism proceeds via oxidative addition of the acetylenic CH bond to RhI, an ene‐type cyclization to the vinylidenecarbene–RhI intermediate, and an electrophilic aromatic substitution with the vinylidenecarbene species. It

  高效的Rh我benzylallene炔烃的催化的环异构产生的三环[9.4.0.0 3,8 ] pentadecapentaene骨架通过C  H键活化以良好的收率。可能的反应机理是通过将炔属CH键氧化加至Rh I，烯型环化至亚乙烯基卡宾–Rh I中间体以及用亚乙烯基卡宾进行亲电芳族取代而进行的。它是基于氘和竞争实验提出的。
• Palladium-catalyzed arylation of vinylic acetates. Phosphine ligand influenced regioselectivity
  作者：Mickaël Jean、Jacques Renault、Pierre van de Weghe

  DOI：10.1016/j.tetlet.2009.09.048

  日期：2009.11

  A palladium-catalyzed coupling reaction of aryl bromides with vinylic acetates in the presence of tributyltin methoxide has been described. The α-arylation aldehyde product and the aryl ketone were obtained in the presence of P(t-Bu)3 and P(o-Tol)3, respectively.

  已经描述了在甲醇三丁基锡存在下钯催化的芳基溴化物与乙酸乙烯酯的偶联反应。在存在P（t -Bu）3和P（o- Tol）3的情况下分别获得了α-芳基化醛产物和芳基酮。
• Palladium-Catalyzed Site-Selective C(sp³)–H Arylation of Phenylacetaldehydes
  作者：Bo-Bo Gou、Hang-Fan Liu、Jie Chen、Ling Zhou

  DOI：10.1021/acs.orglett.9b02650

  日期：2019.9.6

  describe a Pd-catalyzed selective C-H arylation reaction of phenylacetaldehydes using l-valine as the transient directing group. This process showed a broad substrate scope and excellent selectivity in which a ligand-controlled functionalization of the unactivated β-C(sp3)-H bond. In addition, enantioselective arylation of phenylacetaldehydes was preliminarily explored by utilizing a bulky chiral transient

  我们描述了使用L-缬氨酸作为瞬时导向基团的Pd催化的苯乙醛的选择性CH芳基化反应。此过程显示出广泛的底物范围和出色的选择性，其中未活化的β-C（sp3）-H键的配体控制功能化。此外，通过利用庞大的手性瞬态导向基团初步研究了苯乙醛的对映选择性芳基化。
• Regioselective 1,2-Diol Rearrangement by Controlling the Loading of BF₃·Et₂O and Its Application to the Synthesis of Related Nor-Sesquiterene- and Sesquiterene-Type Marine Natural Products
  作者：Jun-Li Wang、Hui-Jing Li、Hong-Shuang Wang、Yan-Chao Wu

  DOI：10.1021/acs.orglett.7b01679

  日期：2017.7.21

  achieved by controlling the loading of BF3·Et2O. Its applicability is showcased by the divergent synthesis of austrodoral, austrodoric acid, and 8-epi-11-nordriman-9-one, as well as a formal synthesis of siphonodictyal B and liphagal. A new light is shed on piancol-type rearrangements that will be useful in diversity-oriented synthesis of related natural products.

  通过控制BF 3 ·Et 2 O的负载，实现了1,2-二醇的区域控制重排。其适用性通过奥氏体，奥氏多酸和8- Epi -11-nordriman-9-one的发散合成得以展示。，以及虹吸管B和脂蛋白的正式合成。有关piancol类型重排的新见解，将在相关天然产物的面向多样性的合成中有用。
• Method of treating resistant tumors
  申请人：Wyeth Holdings Corporation

  公开号：US20040121965A1

  公开（公告）日：2004-06-24

  The invention provides a method of treating or inhibiting the growth of or eradicating a tumor in a mammal in need thereof wherein said tumor is resistant to at least one chemotherapeutic agent which method comprises providing to said mammal an effective amount of a compound of Formula II or a pharmaceutically acceptable salt thereof.

  本发明提供了一种治疗或抑制哺乳动物体内对至少一种化疗药物产生耐药性的肿瘤生长或根除肿瘤的方法，该方法包括向该哺乳动物提供有效量的公式II化合物或其药学上可接受的盐。