[Diphenyl-[12-(phenylmethoxymethoxy)dodecoxy]methyl]benzene | 1186520-60-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: [Diphenyl-[12-(phenylmethoxymethoxy)dodecoxy]methyl]benzene
• 英文别名: [diphenyl-[12-(phenylmethoxymethoxy)dodecoxy]methyl]benzene
• CAS: 1186520-60-4
• 化学式: C₃₉H₄₈O₃
• 分子量: 564.808
• InChiKey: SEXMSORQEDVEJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  42
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [Diphenyl-[12-(phenylmethoxymethoxy)dodecoxy]methyl]benzene 在 2,2'-联吡啶 、 三氟甲磺酸三甲基硅酯 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以84%的产率得到12-(trityloxy)-1-dodecanol
  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：

  三苯基氯甲烷 在 四丁基碘化铵 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 44.5h， 生成 [Diphenyl-[12-(phenylmethoxymethoxy)dodecoxy]methyl]benzene
  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

• 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。