methyl 4-benzyloxy-2-methoxymethyloxybenzoate | 422566-44-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-benzyloxy-2-methoxymethyloxybenzoate
• 英文别名: Methyl 2-(methoxymethoxy)-4-phenylmethoxybenzoate
• CAS: 422566-44-7
• 化学式: C₁₇H₁₈O₅
• 分子量: 302.327
• InChiKey: ULVCWKSSJSVQMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-benzyloxy-2-methoxymethyloxybenzoate 在 silica-immobilized p-TsOH 作用下， 以 甲苯 为溶剂， 反应 0.42h， 以99%的产率得到4-(苄氧基)-2-羟基苯甲酸甲酯
  参考文献：
  名称：

  Factors affecting orthogonality in the deprotection of 2,4-di-protected aromatic ethers employing solid-supported acids

  摘要：

  Selective deprotection of aromatic ethers bearing two protecting groups on the same aromatic ring by solid-supported acids (Amberlyst-15 and PTS-Si) was systematically investigated. ortho-Directing protonation by the carbonyl group as well as carbocation stability and quenching are the important determining factors for the orthogonal deprotection process. Stablilized carbocations (e.g., those from the MOM and PMB groups) could be removed with high selectivity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.089
• 作为产物：
  描述：

  4-(苄氧基)-2-羟基苯甲酸甲酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以98%的产率得到methyl 4-benzyloxy-2-methoxymethyloxybenzoate
  参考文献：
  名称：

  Factors affecting orthogonality in the deprotection of 2,4-di-protected aromatic ethers employing solid-supported acids

  摘要：

  Selective deprotection of aromatic ethers bearing two protecting groups on the same aromatic ring by solid-supported acids (Amberlyst-15 and PTS-Si) was systematically investigated. ortho-Directing protonation by the carbonyl group as well as carbocation stability and quenching are the important determining factors for the orthogonal deprotection process. Stablilized carbocations (e.g., those from the MOM and PMB groups) could be removed with high selectivity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.089

文献信息

• Synthesis and Structure−Activity Relationship Study of Lamellarin Derivatives
  作者：Fumito Ishibashi、Shinji Tanabe、Tatsuya Oda、Masatomo Iwao

  DOI：10.1021/np0104525

  日期：2002.4.1

  Ten derivatives (3-12) of marine alkaloid lamellarin D (1) were synthesized and evaluated for cytotoxicity against a HeLa cell line in an effort to examine their structure-activity relationships. It appeared that the hydroxyl groups at positions C-8 and C-20 of 1 were important structural requirements for cytotoxic activity, while the hydroxyl group at C-14 and the two methoxy groups at C-13 and C-21 were not necessary for the activity.
• Factors affecting orthogonality in the deprotection of 2,4-di-protected aromatic ethers employing solid-supported acids
  作者：Kassrin Tangdenpaisal、Supannee Sualek、Somsak Ruchirawat、Poonsakdi Ploypradith

  DOI：10.1016/j.tet.2009.03.089

  日期：2009.5

  Selective deprotection of aromatic ethers bearing two protecting groups on the same aromatic ring by solid-supported acids (Amberlyst-15 and PTS-Si) was systematically investigated. ortho-Directing protonation by the carbonyl group as well as carbocation stability and quenching are the important determining factors for the orthogonal deprotection process. Stablilized carbocations (e.g., those from the MOM and PMB groups) could be removed with high selectivity. (C) 2009 Elsevier Ltd. All rights reserved.