(Z)-2-(4'-methylphenyl)-3-N,N-dimethylaminopropenal | 53868-45-4

• 物质功能分类: 化学试剂 - 有机试剂 - 芳香醛(含缩醛,半缩醛)
• 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: (Z)-2-(4'-methylphenyl)-3-N,N-dimethylaminopropenal
• 英文别名: 2-(4'-methylphenyl)malondialdehyde；4-methylphenyl malonaldehyde；(2Z)-3-hydroxy-2-(4-methylphenyl)prop-2-enal；(Z)-3-hydroxy-2-(4-methylphenyl)prop-2-enal
• CAS: 53868-45-4
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: FKRKKHBTIIWVGU-UXBLZVDNSA-N

物化性质

• 熔点：
  128-132 °C
• 沸点：
  228.88°C (rough estimate)
• 密度：
  1.0281 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 危险类别码：
  R22,R36,R51
• 海关编码：
  2912491000

反应信息

• 作为反应物：
  描述：

  (Z)-2-(4'-methylphenyl)-3-N,N-dimethylaminopropenal 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 silver(l) oxide 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 34.58h， 生成 methyl 2,3,4-tri-O-acetyl-(2'-(4''-methylphenyl)-3'-(4'''-methoxybenzylaminocarbonyloxy)-1'-(E)-propenyloxy)-β-D-glucopyranosiduronate
  参考文献：
  名称：

  A new linker for glucuronylated anticancer prodrugs

  摘要：

  The synthesis, enzymatic hydrolysis and self decomposition of model glucuronylated prodrugs, incorporating a new linker with different aryl substituents, have been studied. Determination of kinetic parameters (V-max, K-m and t(1/2)) showed the important role of aromatic substitution in enzymatic recognition and linker decomposition. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.11.026

文献信息

• Synthesis and Initial SAR Studies of 3,6-Disubstituted Pyrazolo[1,5-a]pyrimidines: A New Class of KDR Kinase Inhibitors
  作者：Mark E. Fraley、William F. Hoffman、Robert S. Rubino、Randall W. Hungate、Andrew J. Tebben、Ruth Z. Rutledge、Rosemary C. McFall、William R. Huckle、Richard L. Kendall、Kathleen E. Coll、Kenneth A. Thomas

  DOI：10.1016/s0960-894x(02)00525-5

  日期：2002.10

  synthesized and evaluated the activity of 3,6-disubstituted pyrazolo[1,5-a]pyrimidines as a new class of KDR kinase inhibitors. Starting with screening lead 1, potency against isolated KDR was fully optimized with 3-thienyl and 4-methoxyphenyl substituents at the 6- and 3-positions (3g, KDR IC(50)=19 nM), respectively. The synthesis and SAR of these compounds are described.

  我们已经合成并评估了3,6-二取代的吡唑并[1,5-a]嘧啶作为一类新的KDR激酶抑制剂的活性。从筛选铅1开始，分别在6位和3位（3g，KDR IC（50）= 19 nM）处使用3-噻吩基和4-甲氧基苯基取代基完全优化了对分离的KDR的效力。描述了这些化合物的合成和SAR。
• Structure-dependent intermolecular hydrogen-bond effects on carbon-13 NMR chemical shifts in enol forms of 1,3-diketones
  作者：Fumio Imashiro、Shiro Maeda、Kiyonori Takegoshi、Takehiko Terao、A. Saika

  DOI：10.1021/ja00251a028

  日期：1987.8
• A new spacer group derived from arylmalonaldehydes for glucuronylated prodrugs
  作者：Sébastien Papot、Damien Combaud、Jean-Pierre Gesson

  DOI：10.1016/s0960-894x(98)00454-5

  日期：1998.9

  A new glucuronylated prodrug of doxorubicin, potentially useful for ADEPT or PMT cancer chemotherapy, has been prepared from 4-methyl phenyl malonaldehyde. The enol ether spacer, linked via a carbamate to the 3'-amino group of doxorubicin is rapidly cleaved after beta-glucuronidase (E coli) catalyzed hydrolysis at pH 7.2 and 37 degrees C. (C) 1998 Elsevier Science Ltd. All rights reserved.
• A new simple and convenient method for the synthesis of substituted 2,6,9-trioxabicyclo[3.3.1]-nona-3,7-dienes from arylmalondialdehydes
  作者：Anthony Fernandes、Jérôme Marrot、Jean-Pierre Gesson、Sébastien Papot

  DOI：10.1016/j.tetlet.2006.06.043

  日期：2006.8

  A new convenient synthesis of substituted 2,6,9-trioxabicyclo[3.3.1]-nona-3,7-dienes is described. These new 'bridged bis-dioxines' were obtained in moderate to good yields by dimerization of the corresponding arylmalondialdehydes in the presence of 0.5 equiv of TMSOTf. The structure of the nitro derivative le has been proven by X-ray crystallography. A mechanism for this reaction is proposed. (c) 2006 Elsevier Ltd. All rights reserved.
• COPPOLA G. M.; FRASER J. D.; HARDTMANN G. E.; HUEGI B. S.; KATHAWALA F. G+, J. HETEROCYCL. CHEM., 1979, 16, NO 3, 545-554
  作者：COPPOLA G. M.、 FRASER J. D.、 HARDTMANN G. E.、 HUEGI B. S.、 KATHAWALA F. G+

  DOI：——

  日期：——