10-methoxymethoxydecanol | 175914-87-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 10-methoxymethoxydecanol
• 英文别名: 10-(methoxymethoxy)decan-1-ol；10-(Methoxymethoxy)-1-decanol
• CAS: 175914-87-1
• 化学式: C₁₂H₂₆O₃
• 分子量: 218.337
• InChiKey: XOIIDUAEQCFTGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  10-methoxymethoxydecanol 在 盐酸 、 重铬酸吡啶 、 pyridine-SO3 complex 、 sodium hydride 、 二异丁基氢化铝 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 32.0h， 生成 (E)-10-dodecenoic acid
  参考文献：
  名称：

  Structural requirements of dictyopyrones isolated from Dictyostelium spp. in the regulation of Dictyostelium development and in anti-leukemic activity

  摘要：

  Cellular slime molds are fascinating to the field of developmental biology, and have long been used as excellent model organisms for the study of various aspects of multicellular development. We have recently isolated alpha-pyronoids, named dictyopyrones A-D (1-4), from various species of Dictyostelium cellular slime molds, and it was shown that compound 3 may regulate Dictyostelium development. In this study, we synthesized dictyopyrones A-D (1-4) and their analogues, investigated the physiological role of the molecules in cell growth and morphogenesis in D. discoideum, and further verified their effects on human leukemia K562 cells. Nitrogen-containing compounds 22 and 37 strongly inhibited cell growth in K562 leukemia cells, indicating that these compounds may be utilized as novel lead compounds for anti-leukemic agents. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.001
• 作为产物：
  描述：

  triethyl-(10-methoxymethoxy-decyloxy)-silane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 10-methoxymethoxydecanol
  参考文献：
  名称：

  Triethyl- (or Trimethyl-)Silyl Triflate-Catalyzed Reductive Cleavage of Triphenylmethyl (Trityl) Ethers with Triethylsilane

  摘要：

  [GRAPHICS]A triphenylmethyl (trityl) ether was reductively and instantaneously cleaved by triethylsilane in the presence of a catalytic amount of TES- (or TMS)-triflate. The reaction conditions are mild enough to achieve reduction in the presence of a variety of acid-sensitive functional groups. Upon a mild acidic treatment of the crude product, the corresponding alcohol is obtained in high yield.

  DOI：

  10.1021/ol0271988

文献信息

• Reductive cleavage of benzyl ethers with lithium naphthalenide. A convenient method for debenzylation
  作者：Hsing-Jang Liu、Judy Yip、Kak-Shan Shia

  DOI：10.1016/s0040-4039(97)00345-6

  日期：1997.3

  An operationally simple, high-yielding and highly chemoselective procedure has been developed for the conversion of benzyl ethers to the corresponding alcohols, using lithium naphthalenide as the reagent.

  已经开发了一种操作简单，高产率和高度化学选择性的方法，用于使用萘二甲酸锂作为试剂将苄基醚转化为相应的醇。
• Mechanistic Studies on the Organocatalytic α‐Chlorination of Aldehydes: The Role and Nature of Off‐Cycle Intermediates
  作者：Sebastian Ponath、Martina Menger、Lydia Grothues、Manuela Weber、Dieter Lentz、Carsten Strohmann、Mathias Christmann

  DOI：10.1002/anie.201806261

  日期：2018.9.3

  Herein we report the isolation and characterization of aminal intermediates in the organocatalytic α‐chlorination of aldehydes. These species are stable covalent ternary adducts of the substrate, the catalyst and the chlorinating reagent. NMR‐assisted kinetic studies and isotopic labeling experiments with the isolated intermediate did not support its involvement in downstream stereoselective processes

  在这里，我们报告了醛的有机催化 α-氯化中缩醛胺中间体的分离和表征。这些物质是底物、催化剂和氯化试剂的稳定共价三元加合物。NMR 辅助动力学研究和分离中间体的同位素标记实验不支持其参与 Blackmond 提出的下游立体选择性过程。通过调整氯化试剂的反应性，我们能够抑制限速非循环中间体的积累。因此，开发了一种高效且高度对映选择性的催化体系，具有广泛的官能团耐受性。
• Deprotection of mono and dimethoxy phenyl methyl ethers using catalytic amounts of DDQ
  作者：S. Chandrasekhar、G. Sumithra、J.S. Yadav

  DOI：10.1016/0040-4039(96)00081-0

  日期：1996.3

  4-Methoxy and 3,4 dimethoxy benzyl ethers have been deprotected with catalytic amounts of DDQ by oxidative recycling of the byproduct DDHQ with FeCl3 for the first time.

  通过副产物DDHQ首次用FeCl 3氧化再循环，已用催化量的DDQ对4-甲氧基和3,4-二甲氧基苄基醚进行了脱保护。
• Ruthenium Catalyzed Deuterium Labelling of α-Carbon in Primary Alcohol and Primary/Secondary Amine in D₂O
  作者：Masaaki Takahashi、Koichiro Oshima、Seijiro Matsubara

  DOI：10.1246/cl.2005.192

  日期：2005.2

  Primary alcohols and primary/secondary amines are labelled with D atom at α-position regioselectively by means of deuterium oxide and ruthenium catalyst.

  伯醇和伯/仲胺通过氧化氘和钌催化剂在α位区域选择性地用D原子标记。