12-((苄氧基)甲氧基)十二烷酸甲酯 | 1296645-34-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 12-((苄氧基)甲氧基)十二烷酸甲酯
• 英文名称: Methyl 12-(phenylmethoxymethoxy)dodecanoate
• 英文别名: methyl 12-(phenylmethoxymethoxy)dodecanoate
• CAS: 1296645-34-5
• 化学式: C₂₁H₃₄O₄
• 分子量: 350.499
• InChiKey: IRUDUENSDHRHDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  12-((苄氧基)甲氧基)十二烷酸甲酯 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 4.5h， 以95%的产率得到methyl 12-hydroxydodecanoate
  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：

  Methyl 12-(methoxymethoxy)dodecanoate 以 二氯甲烷 为溶剂， 反应 14.5h， 生成 12-((苄氧基)甲氧基)十二烷酸甲酯
  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

• 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.