Diethyl 5-phenylmethoxybenzene-1,3-dicarboxylate | 251912-45-5

• 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: Diethyl 5-phenylmethoxybenzene-1,3-dicarboxylate
• CAS: 251912-45-5
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: CMFDQONILFCUAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Diethyl 5-phenylmethoxybenzene-1,3-dicarboxylate 在 lithium aluminium tetrahydride 、 戴斯-马丁氧化剂 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 O-benzyl-3,5-di(formyl)phenol
  参考文献：
  名称：

  Convenient syntheses of fluorous phenols of the formula HOC6H5−n((CH2)3(CF2)7CF3)n (n=1, 2) and the corresponding triarylphosphites

  摘要：

  The aldehydic benzyl ethers PhCH2OC6H4CHO (2; a/b = para/meta series) are readily available from the corresponding phenols and react with Wittig reagents derived from LPh3PCH2CH2Rf8]I-+(-) (R-f8 = (CF2)(7)CF3) to give PhCH2OC6H4CH=CHCH2Rf8 (86-93%, Z major). Reactions with H-2 over Pd/C give the fluorous phenols HOC6H4(CH2)(3)R-f8 (4a,b; 87-91%). Condensations with PCl3 and NEt3 (3.0:1.0:3.3 mol ratio) give the fluorous phosphites P[OC6H4(CH2)(3)R-f8](3) (5a,b; 92-94%), but traces of 4a,b are difficult to remove. The phthalate-based benzyl ethers PhCH2OC6H3 (COOR)(2) (7; c/d = 3,5/3,4 -OC6H3-3,n-(R)(2) series) are easily accessed and reduced with LiAlH4 to the diols PhCH2OC6H3(CH2OH)(2) (8c,d; 89-90%). Diol 8c and the Dess-Martin periodinane react to give the dialdehyde PhCH2OC6H3(CHO)(2) (9C; 95%). This is elaborated by a sequence analogous to 2 --> 4 --> 5 to the fluorous phenol HOC6H3((CH2)(3)R-f8)(2) (11C; 97%/96%, two steps) and phosphite P[OC6H3((CH2)(3)R-f8)(2)](3) (12c, 92%), from which traces of 11c are difficult to remove. Diol 8d can be similarly elaborated to 11d, but the dialdehyde 9d is labile and the combined yield of the Dess-Martin[Wittig steps is 32%. The CF3C6F11/toluene partition coefficients of 11c,d, and 12c (two pony tails; 70:30, 72:28, 92:8) are much higher than those of 4a and b (one pony tail; 12:88, 14:86). (C) 2002 Elsevier Science B.V.. All rights reserved.

  DOI：

  10.1016/s0022-1139(02)00242-7
• 作为产物：
  描述：

  5-羟基间苯二甲酸二乙酯 、 溴甲苯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 10.0h， 以92%的产率得到Diethyl 5-phenylmethoxybenzene-1,3-dicarboxylate
  参考文献：
  名称：

  三齿 SCS 钯 (II) 配合物：用于 Heck 反应的新型、高度稳定、可回收的催化剂

  摘要：

  一种含有 Pd(II) 的新型钳式 SCS 配体是一种简单、稳健的 Heck 化学催化剂，使用各种烯烃受体和芳基碘化物。它对芳基溴的活性较低。虽然某些钯 (II) 物质缓慢插入到该配体的未取代版本的芳基 C-H 键中，但将活化基团引入芳环的 5 位很容易实现定量金属插入。这些配体是通过简单修饰廉价的起始材料合成并连接到可溶性聚合物上的。例如，5-氧基和 5-酰胺 SCS 配体分别通过醚或酰胺键成功附加到 5000 Mn 聚（乙二醇）上。在空气中的 DMF 溶液中，5-氧代和 5-酰胺配合物都具有作为 Heck 催化剂的活性。PEG 结合的 5-酰胺-SCS-Pd 复合物通过溶剂沉淀循环 3 次，没有观察到催化剂失活。虽然 5-amido-SCS-Pd 配合物非常坚固，但它们的 5-oxo 对应物在 c...

  DOI：

  10.1021/ja991099g

文献信息

• Tridentate SCS Palladium(II) Complexes:  New, Highly Stable, Recyclable Catalysts for the Heck Reaction
  作者：David E. Bergbreiter、Philip L. Osburn、Yun-Shan Liu

  DOI：10.1021/ja991099g

  日期：1999.10.1

  A new pincer-type SCS ligand containing Pd(II) is a simple, robust catalyst for Heck chemistry using a variety of alkene acceptors and aryl iodides. It is less active with aryl bromides. While certain palladium(II) species insert slowly into the aryl C−H bond of an unsubstituted version of this ligand, the introduction of activating groups into the 5 position of the aromatic ring readily allows quantitative

  一种含有 Pd(II) 的新型钳式 SCS 配体是一种简单、稳健的 Heck 化学催化剂，使用各种烯烃受体和芳基碘化物。它对芳基溴的活性较低。虽然某些钯 (II) 物质缓慢插入到该配体的未取代版本的芳基 C-H 键中，但将活化基团引入芳环的 5 位很容易实现定量金属插入。这些配体是通过简单修饰廉价的起始材料合成并连接到可溶性聚合物上的。例如，5-氧基和 5-酰胺 SCS 配体分别通过醚或酰胺键成功附加到 5000 Mn 聚（乙二醇）上。在空气中的 DMF 溶液中，5-氧代和 5-酰胺配合物都具有作为 Heck 催化剂的活性。PEG 结合的 5-酰胺-SCS-Pd 复合物通过溶剂沉淀循环 3 次，没有观察到催化剂失活。虽然 5-amido-SCS-Pd 配合物非常坚固，但它们的 5-oxo 对应物在 c...
• Convenient syntheses of fluorous phenols of the formula HOC6H5−n((CH2)3(CF2)7CF3)n (n=1, 2) and the corresponding triarylphosphites
  作者：Sylvie Le Stang、Ralf Meier、Christian Rocaboy、J.A Gladysz

  DOI：10.1016/s0022-1139(02)00242-7

  日期：2003.2

  The aldehydic benzyl ethers PhCH2OC6H4CHO (2; a/b = para/meta series) are readily available from the corresponding phenols and react with Wittig reagents derived from LPh3PCH2CH2Rf8]I-+(-) (R-f8 = (CF2)(7)CF3) to give PhCH2OC6H4CH=CHCH2Rf8 (86-93%, Z major). Reactions with H-2 over Pd/C give the fluorous phenols HOC6H4(CH2)(3)R-f8 (4a,b; 87-91%). Condensations with PCl3 and NEt3 (3.0:1.0:3.3 mol ratio) give the fluorous phosphites P[OC6H4(CH2)(3)R-f8](3) (5a,b; 92-94%), but traces of 4a,b are difficult to remove. The phthalate-based benzyl ethers PhCH2OC6H3 (COOR)(2) (7; c/d = 3,5/3,4 -OC6H3-3,n-(R)(2) series) are easily accessed and reduced with LiAlH4 to the diols PhCH2OC6H3(CH2OH)(2) (8c,d; 89-90%). Diol 8c and the Dess-Martin periodinane react to give the dialdehyde PhCH2OC6H3(CHO)(2) (9C; 95%). This is elaborated by a sequence analogous to 2 --> 4 --> 5 to the fluorous phenol HOC6H3((CH2)(3)R-f8)(2) (11C; 97%/96%, two steps) and phosphite P[OC6H3((CH2)(3)R-f8)(2)](3) (12c, 92%), from which traces of 11c are difficult to remove. Diol 8d can be similarly elaborated to 11d, but the dialdehyde 9d is labile and the combined yield of the Dess-Martin[Wittig steps is 32%. The CF3C6F11/toluene partition coefficients of 11c,d, and 12c (two pony tails; 70:30, 72:28, 92:8) are much higher than those of 4a and b (one pony tail; 12:88, 14:86). (C) 2002 Elsevier Science B.V.. All rights reserved.