12-methoxymethoxydodecanol | 736177-57-4

• 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: 12-methoxymethoxydodecanol
• 英文别名: 12-(methoxymethoxy)dodecan-1-ol
• CAS: 736177-57-4
• 化学式: C₁₄H₃₀O₃
• 分子量: 246.39
• InChiKey: VHNCESNEIDNNPK-UHFFFAOYSA-N

物化性质

• 沸点：
  320.9±12.0 °C(Predicted)
• 密度：
  0.913±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  12-methoxymethoxydodecanol 在 盐酸 、 4-二甲氨基吡啶 、 重铬酸吡啶 、 pyridine-SO3 complex 、 sodium hydride 、 二异丁基氢化铝 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 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 4.0h， 生成 5-((E)-1-Hydroxy-tetradec-12-enylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione
  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：

  Methoxy-acetic acid 12-methoxymethoxy-dodecyl ester 在 ytterbium(III) triflate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以99%的产率得到12-methoxymethoxydodecanol
  参考文献：
  名称：

  Ytterbium(III) Triflate-Catalyzed Selective Methanolysis of Methoxyacetates:  A New Deprotective Method

  摘要：

  DOI：

  10.1021/jo960095g

文献信息

• Remarkable effect of 2,2′-bipyridyl: mild and highly chemoselective deprotection of methoxymethyl (MOM) ethers in combination with TMSOTf (TESOTf)–2,2′-bipyridyl
  作者：Hiromichi Fujioka、Ozora Kubo、Kento Senami、Yutaka Minamitsuji、Tomohiro Maegawa

  DOI：10.1039/b907910f

  日期：——

  The remarkable effect of 2,2′-bipyridyl led to the successful development of the mild and highly chemoselective deprotection method of methoxymethyl (MOM) ethers using the combination of TMSOTf (or TESOTf) and 2,2′-bipyridyl; this method can be applied to the direct conversion of the MOM group to other ethereal protective groups (e.g.benzyloxymethyl) with the corresponding alcohols.

  2,2'-联吡啶的显著效果促成了甲氧基甲基（MOM）醚的温和且高度化学选择性的去保护方法的成功开发，该方法结合了TMSOTf（或TESOTf）和2,2'-联吡啶；该方法可以直接将MOM基团转化为其他醚类保护基团（例如苄氧基甲基）及相应的醇。
• Identification and Total Synthesis of Two Previously Unreported Odd-Chain Bis-Methylene-Interrupted Fatty Acids with a Terminal Olefin that Activate Protein Phosphatase, Mg2+/Mn2+-Dependent 1A (PPM1A) in Ovaries of the Limpet Cellana toreuma
  作者：Hideki Kawashima、Naoki Toyooka、Takuya Okada、Huy Du Nguyen、Yuya Nishikawa、Yuka Miura、Nana Inoue、Ken-ichi Kimura

  DOI：10.3390/md17070410

  日期：——

  Diverse non-methylene-interrupted (NMI) fatty acids (FAs) with odd-chain lengths have been recognized in triacylglycerols and polar lipids from the ovaries of the limpet Cellana toreuma, however their biological properties remain unclear. In this study, two previously unreported odd-chain NMI FAs, (12Z)-12,16-heptadecadienoic (1) and (14Z)-14,18-nonadecadienoic (2) acids, from the ovary lipids of C. toreuma were identified by a combination of equivalent chain length (ECL) values of their methyl esters and capillary gas chromatography-mass spectrometry (GC-MS) of their 3-pyridylcarbinol derivatives. On the basis of the experimental results, both 1 and 2 were synthesized to prove their structural assignments and to test their biological activity. The ECL values and electron impact-mass (EI-MS) spectra of naturally occurring 1 and 2 were in agreement with those of the synthesized 1 and 2. In an in vitro assay, both 1 and 2 activated protein phosphatase, Mg2+/Mn2+-dependent 1A (PPM1A) up to 100 μM in a dose-dependent manner.

  来自巴石螺卵巢的三酰甘油和极性脂质中已经发现了多种不含亚甲基间断(NMI)的奇数碳链长度脂肪酸(FA)，但它们的生物学特性仍不清楚。本研究通过相当链长(ECL)值的甲酯和毛细管气相色谱-质谱(GC-MS)的3-吡啶甲醇衍生物鉴定出了巴石螺卵巢脂质中两种未报道的奇数碳链NMI FA，即(12Z)-12,16-庚二烯酸(1)和(14Z)-14,18-十九二烯酸(2)。在实验结果的基础上，合成了1和2来证明它们的结构分配和测试它们的生物活性。天然存在的1和2的ECL值和电子轰击质谱(EI-MS)谱与合成的1和2一致。在体外实验中，1和2均以剂量依赖的方式使蛋白磷酸酶、Mg2+/Mn2+依赖型1A(PPM1A)活化高达100μM。
• The reaction of acetal-type protective groups in combination with TMSOTf and 2,2′-bipyridyl; mild and chemoselective deprotection and direct conversion to other protective groups
  作者：Hiromichi Fujioka、Yutaka Minamitsuji、Ozora Kubo、Kento Senami、Tomohiro Maegawa

  DOI：10.1016/j.tet.2011.02.048

  日期：2011.4

  A mild and chemoselective deprotection method of various acetal-type protective groups, such as MOM, MEM, BOM, and SEM ethers, has been developed. The combination of TMSOTf and 2,2'-bipyridyl was very effective for the deprotection, and the reaction proceeded via the formation of pyridinium intermediates, which were hydrolyzed to the corresponding alcohols in good to high yields. The features of this method are mild (almost neutral) reaction conditions and the tolerability of acid-sensitive functional groups. This method is also applicable for the direct conversion of MOM ether to BOM or SEM ether using the appropriate alcohols instead of H2O. (C) 2011 Elsevier Ltd. All rights reserved.