8-(methoxymethoxy)octanal | 91898-42-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-(methoxymethoxy)octanal
• CAS: 91898-42-9
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: GXJCOQWQKPSQKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  8-(methoxymethoxy)octanal 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 水 、 叔丁醇 为溶剂， 反应 1.0h， 以100%的产率得到8-(methoxymethoxy)octanoic acid
  参考文献：
  名称：

  N-甲氧基酰胺对铜催化有机三氟硼酸盐的亲电酰胺化

  摘要：

  据报道，使用N-甲氧基酰胺进行了铜催化的芳基三氟硼酸酯的亲电酰胺化反应。该反应显示出源自两个明显特征的高官能团相容性：1）N-甲氧基酰胺的高稳定性，以及2）在LiCl存在下的非碱性温和条件。所开发的方法还可以用于合成广泛分布于天然产物中的烯酰胺。初步的机理研究表明，第一步是在LiCl的协助下对三氟硼酸芳基酯进行金属转移，生成的芳基铜中间体通过非S N 2氧化添加至N-甲氧基酰胺并随后进行还原消除而提供了苯胺。

  DOI：

  10.1002/chem.201901145
• 作为产物：
  描述：

  1,1-Dimethoxy-8-(methoxymethoxy)octane 在 二甲基溴化硼 、 碳酸氢钠 作用下， 生成 8-(methoxymethoxy)octanal
  参考文献：
  名称：

  Dimethylboron bromide and diphenylboron bromide: cleavage of acetals and ketals

  摘要：

  DOI：

  10.1021/jo00195a007

文献信息

• In Situ Generated (Hypo)Iodite Catalysts for the Direct α-Oxyacylation of Carbonyl Compounds with Carboxylic Acids
  作者：Muhammet Uyanik、Daisuke Suzuki、Takeshi Yasui、Kazuaki Ishihara

  DOI：10.1002/anie.201101522

  日期：2011.5.27

  It′s the iodine: The intra‐ and intermolecular title reaction is catalyzed by an in situ generated ammonium (hypo)iodite species. Either H2O2 or tert‐butyl hydroperoxide (TBHP) can be used as an environmentally benign oxidant and a wide range of substrates react to give the corresponding α‐acyloxycarbonyl compounds in good to excellent yields.

  它是碘：分子内和分子间标题反应是由原位生成的亚碘铵（次同）催化的。H 2 O 2或叔丁基氢过氧化物（TBHP）都可以用作环境友好的氧化剂，并且多种底物反应生成相应的α-酰氧基羰基化合物，收率良好至优异。
• Pyrimidine nucleoside derivatives having anti-tumor activity, their preparation and use
  申请人：Sankyo Company Limited

  公开号：EP0536936A1

  公开（公告）日：1993-04-14

  Compounds of formula (I): [in which: R¹, R² and R³ are the same or different and each represents a hydrogen atom, an optionally substituted alkanoyl group or an alkenylcarbonyl group, provided that at least one of R¹, R² and R³ represents an unsubstituted alkanoyl group having from 5 to 24 carbon atoms, said substituted alkanoyl group or said alkenylcarbonyl group; and one of R⁴ and R⁵ represents a hydrogen atom and the other represents a cyano group]; have valuable anti-tumour activity.

  式子（I）的化合物：[其中：R¹、R²和R³相同或不同，每个代表氢原子、可选取代的脂肪酰基团或烯基羰基团，前提是至少有一个R¹、R²和R³代表有5到24个碳原子的未取代脂肪酰基团，或者是所述取代的脂肪酰基团或所述烯基羰基团；R⁴和R⁵中的一个代表氢原子，另一个代表氰基]，具有有价值的抗肿瘤活性。
• Hypoiodite‐Catalyzed Oxidative α‐C−N Coupling of Ketones with Imides and Azoles
  作者：Mayuko Tsukahara、Muhammet Uyanik、Kazuaki Ishihara

  DOI：10.1002/adsc.202300716

  日期：2023.8.15

  Herein, we report a direct method for the synthesis of α-imidoketones and α-azolylketones via hypoiodite-catalyzed oxidative α-C−N coupling of ketones with the corresponding imides and azoles, respectively. The use of inorganic base additives such as cesium carbonate in the presence of 18-crown-6 as a phase transfer catalyst was crucial to induce high reactivity. Control experiments revealed that the

  在此，我们报道了一种通过次碘酸盐催化酮与相应酰亚​​胺和唑的氧化 α-C−N 偶联直接合成 α-亚胺酮和 α-唑基酮的方法。在 18-crown-6 存在下使用碳酸铯等无机碱添加剂作为相转移催化剂对于诱导高反应性至关重要。对照实验表明，碱性添加剂不仅可能促进高周转次碘酸盐催化，而且还参与偶联配偶体的活化。
• Practical One-Pot Di-O-silylation and Regioselective Deprotective Oxidation of 1⁰-<i>O</i>-Silyl Ether in 1⁰,2⁰-Diols
  作者：S. Chandrasekhar、Pradyumna K. Mohanty、Mohamed Takhi

  DOI：10.1021/jo9621175

  日期：1997.4.1
• Polar 3-alkylidene-5-pivaloyloxymethyl-5′-hydroxymethyl-γ-lactones as protein kinase C ligands and antitumor agents
  作者：Ji-Hye Kang、Yerim Kim、Shin-Hye Won、Song-Kyu Park、Chang Woo Lee、Hwan-Mook Kim、Nancy E. Lewin、Nicholas A. Perry、Larry V. Pearce、Daniel J. Lundberg、Robert J. Surawski、Peter M. Blumberg、Jeewoo Lee

  DOI：10.1016/j.bmcl.2009.12.058

  日期：2010.2

  A series of DAG-lactones with polar 3-alkylidene substituents have been investigated as PKC-alpha ligands and antitumor agents. Extensive analysis of structure-activity relationships for the 3-alkylidene chain revealed that polar groups such as ether, hydroxyl, aldehyde, ester, acyloxy, and amido were tolerated with similar binding affinities and reduced lipophilicities compared to the corresponding unsubstituted alkylidene chain. Among the derivatives, compounds 5, 6 and 8 with an ether type of side chain showed high binding affinities in range of K-i = 3-5 nM and excellent antitumor profiles, particularly against the colo205 colon cancer and the K562 leukemia cell lines. (c) 2010 Elsevier Ltd. All rights reserved.