2,4-bis-methoxymethoxy-6-methyl-3-(2-oxoethyl)benzaldehyde | 868135-98-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,4-bis-methoxymethoxy-6-methyl-3-(2-oxoethyl)benzaldehyde
• 英文别名: 2,4-Bis(methoxymethoxy)-6-methyl-3-(2-oxoethyl)benzaldehyde
• CAS: 868135-98-2
• 化学式: C₁₄H₁₈O₆
• 分子量: 282.293
• InChiKey: QMWBENXEAJHKGC-UHFFFAOYSA-N

物化性质

• 沸点：
  447.6±45.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,4-bis-methoxymethoxy-6-methyl-3-(2-oxoethyl)benzaldehyde 在 chromium dichloride 、 盐酸 、 水 、 nickel dichloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 UTKO4
  参考文献：
  名称：

  Synthesis and anti-migrative evaluation of moverastin derivatives

  摘要：

  Cell migration of tumor cells is essential for invasion of the extracellular matrix and for cell dissemination. Inhibition of the cell migration involved in the invasion process represents a potential therapeutic approach to the treatment of tumor metastasis; therefore, a novel series of derivatives of moverastins (moverastins A and B), an inhibitor of tumor cell migration, was designed and chemically synthesized. Among these moverastin derivatives, several compounds showed stronger cell migration inhibitory activity than parental moverastins, and UTKO1 was found to have the most potent inhibitory activity against the migration of human esophageal tumor EC17 cells in a chemotaxis cell chamber assay. Interestingly, although moverastins are considered to inhibit tumor cell migration by inhibiting farnesyltransferase (FTase), UTKO1 did not inhibit FTase, indicating that UTKO1 inhibited tumor cell migration by a mechanism other than the inhibition of FTase. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.028

文献信息

• Unified synthesis and assessment of tumor cell migration inhibitory activity of optically active UTKO1, originally designed moverastin analog
  作者：Yusuke Ogura、Hiroki Kobayashi、Masaya Imoto、Hidenori Watanabe、Hirosato Takikawa

  DOI：10.1093/bbb/zbaa062

  日期：2021.1.7

  a mixture of the stereoisomers. In this study, a concise and unified synthesis of the 4 optically active stereoisomers of UTKO1 was achieved from a known optically pure dihydro-α-ionone through a 5-step sequence. The key transformation in the synthesis was a Nozaki-Hiyama-Kishi (NHK) reaction between an optically active enoltriflate and a known aldehyde to install the chiral allylic hydroxy group at

  UTKO1 是一种天然肿瘤细胞迁移抑制剂 moverastin 的合成类似物，从 Aspergillus sp. 的微生物提取物中分离出来。7720. UTKO1 最初是作为立体异构体的混合物开发的。在这项研究中，从已知的光学纯二氢-α-紫罗兰酮通过 5 步序列实现了 UTKO1 的 4 种光学活性立体异构体的简洁统一合成。合成中的关键转化是光学活性烯醇四氟甲磺酸酯和已知醛之间的 Nozaki-Hiyama-Kishi (NHK) 反应，以在 C2' 上安装手性烯丙基羟基。通过使用 Nemoto 的光学拆分试剂 (S)- 或 (R)-5-烯丙基-2-氧杂双环 [3.3.0] 衍生化为相应的缩醛，可以对烯丙基羟基的 2 种非对映异构体进行简单的色谱分离辛烯 (ALBO)。