1-benzyloxy-3,4-dihydroxymethylbenzene | 174728-80-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-benzyloxy-3,4-dihydroxymethylbenzene
• 英文别名: [2-(Hydroxymethyl)-4-phenylmethoxyphenyl]methanol
• CAS: 174728-80-4
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: WAKZNICVMKEEJG-UHFFFAOYSA-N

物化性质

• 沸点：
  443.9±40.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyloxy-3,4-dihydroxymethylbenzene 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 4-Phenylmethoxyphthalaldehyde
  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：

  4-羟基邻苯二甲酸 在 lithium aluminium tetrahydride 、 硫酸 、 potassium carbonate 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 18.0h， 生成 1-benzyloxy-3,4-dihydroxymethylbenzene
  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

文献信息

• A Systematic Study of Peripherally Multiple Aromatic Ester-Functionalized Poly(benzyl ether) Dendrons for the Fabrication of Organogels: Structure-Property Relationships and Thixotropic Property
  作者：Yu Feng、Zhi-Xiong Liu、Hui Chen、Zhi-Chao Yan、Yan-Mei He、Chen-Yang Liu、Qing-Hua Fan

  DOI：10.1002/chem.201400157

  日期：2014.6.2

  A new class of peripherally multiple aromatic ester‐functionalized poly(benzyl ether) dendrons and/or dendrimers with different focal point substituents, surface groups, interior structures, as well as different generations have been synthesized and their structure–property relationships with respect to their gelation ability have been investigated systematically. Most of these dendrons are able to

  合成了具有不同焦点取代基，表面基团，内部结构以及不同世代的一类新型的由外围芳族酯官能化的聚（苄基醚）树枝状和/或树枝状大分子，并且它们之间的结构-性质关系系统地研究了胶凝能力。这些树突中的大多数都能够在很宽的极性范围内凝胶化有机溶剂。不仅在胶凝能力上而且在热致，形态和流变学特征中均观察到明显的树突作用。公开了外围酯官能度和内部树状结构的细微变化显着影响了树突的胶凝行为。在研究的所有树突中，第二代和第三代树突以邻苯二甲酸间苯二甲酸二甲酯（DMIP）为外围基团的G 0 G 2 -Me和G 0 G 3 -Me表现出最佳的胶凝能力，并且在22种以上的芳香族和极性有机溶剂中形成了稳定的凝胶。最低临界胶凝浓度（CGC）达到2.0 mg mL -1，表明一个树枝状分子可截留约1.35×10 4个溶剂分子。通过结合单晶/粉末X射线衍射（XRD）分析和浓度依赖性（CD）/温度依赖性（TD）1来进一步研究凝胶形成的驱动力11
• ANTIVIRAL AGENT CONTAINING BENZODITHIIN DERIVATIVE AS ACTIVE INGREDIENT
  申请人：Rational Drug Design Laboratories

  公开号：EP0770609A1

  公开（公告）日：1997-05-02

  Antiviral agents comprising, as an active ingredient, a 1,4-dihydro-2,3-benzodithiin derivative of the formula wherein each symbol is as defined in the Specification, or a pharmacologically acceptable salt thereof. The antiviral agents of the present invention have superior antiviral activity and are effective for the preventive and therapeutic treatment of viral diseases caused typically by RS virus.

  抗病毒剂，其活性成分包括式 1,4-二氢-2,3-苯并二硫鎓衍生物 其中各符号如说明书中所定义，或其药理上可接受的盐。本发明的抗病毒剂具有优异的抗病毒活性，可有效预防和治疗通常由 RS 病毒引起的病毒性疾病。
• US5698580A
  申请人：——

  公开号：US5698580A

  公开（公告）日：1997-12-16
• 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.