1-(甲氧基甲氧基)癸烷 | 143741-87-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(甲氧基甲氧基)癸烷
• 英文名称: decyl methoxymethyl ether
• 英文别名: n-decylmethoxymethylether；Decane, 1-(methoxymethoxy)-；1-(methoxymethoxy)decane
• CAS: 143741-87-1
• 化学式: C₁₂H₂₆O₂
• 分子量: 202.337
• InChiKey: BRZBSDKACWCZFT-UHFFFAOYSA-N

物化性质

• 沸点：
  241.5±8.0 °C(Predicted)
• 密度：
  0.845±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  14
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(甲氧基甲氧基)癸烷 在 2,2'-联吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 47.0h， 生成 癸醇
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tet.2011.02.048
• 作为产物：
  描述：

  (((癸氧基)甲氧基)甲基)苯 在 4-二甲氨基吡啶 、 2,2'-联吡啶 、 三氟甲磺酸三甲基硅酯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 生成 1-(甲氧基甲氧基)癸烷
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tet.2011.02.048

文献信息

• A Mild and Versatile Method for the Synthesis of Alkyl Ethers from Methoxymethyl Ethers and Application to the Preparation of Sterically Crowded Ethers
  作者：Yutaka Minamitsuji、Atsuhisa Kawaguchi、Ozora Kubo、Yoshifumi Ueyama、Tomohiro Maegawa、Hiromichi Fujioka

  DOI：10.1002/adsc.201200290

  日期：2012.7.9

  A mild and divergent route for the synthesis of alkyl ethers from methoxymethyl (MOM) and methoxyethyl (ME) ether derivatives via pyridinium‐type salt intermediates has been developed. The addition of organocuprates to the salts afforded the corresponding alkyl ethers, including highly crowded ones, in high yields even in the presence of acid‐ or base‐sensitive functional groups.

  通过吡啶鎓盐类中间体，从甲氧基甲基（MOM）和甲氧基乙基（ME）醚衍生物合成烷基醚的温和而多样化的路线已被开发出来。向盐中添加有机铜盐即使在对酸或碱敏感的官能团存在的情况下，也能以高收率获得相应的烷基醚，包括高度拥挤的烷基醚。
• 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。
• Versatile and chemoselective synthesis of fluorinated methyl ethers from methoxymethyl ethers
  作者：Reiya Ohta、Yuichi Kuboki、Yuki Yoshikawa、Yasuyuki Koutani、Tomohiro Maegawa、Hiromichi Fujioka

  DOI：10.1016/j.jfluchem.2017.07.007

  日期：2017.9

  developed for the synthesis of aliphatic fluorinated methyl ethers (ROCH2RF), specifically monofluoromethyl ethers (ROCH2F) and trifluoromethylthiomethyl ethers (ROCH2SCF3), through pyridinium-type salt intermediates derived from methoxymethyl (MOM) ethers. The addition of a fluorine source (F− or SCF3−) to the pyridinium-type salts afforded the corresponding fluorinated methyl ethers in good yields under

  通过衍生自甲氧基甲基的吡啶鎓盐类中间体，已开发出一种通用的化学选择路线，用于合成脂族氟化甲基醚（ROCH 2 R F），特别是一氟甲基醚（ROCH 2 F）和三氟甲基硫代甲基醚（ROCH 2 SCF 3）。 （MOM）醚。加入氟源的（F -或SCF 3 - ）的吡啶鎓盐型得到良好的收率相应的氟化甲基醚温和的条件下。值得注意的是，单氟甲基醚的合成仅在5分钟内即可完成。
• Kantam, M. Lakshmi; Santhi, P. Lakshmi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 3, p. 260 - 261
  作者：Kantam, M. Lakshmi、Santhi, P. Lakshmi

  DOI：——

  日期：——
• A simple and highly efficient deprotecting method for methoxymethyl and methoxyethoxymethyl ethers and methoxyethoxymethyl esters
  作者：Adam Shih-Yuan Lee、Yi-Jung Hu、Shu-Fang Chu

  DOI：10.1016/s0040-4020(01)00062-x

  日期：2001.3