2,6-bis-diethylaminomethyl-phenol | 60365-79-9

• 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: 2,6-bis-diethylaminomethyl-phenol
• 英文别名: 1-HO-2,6-[N(C2H5)2CH2]C6H4；2,6-Bis-diaethylaminomethyl-phenol；2,6-Bis-(diethylaminomethyl)-phenol；2,6-bis(diethylaminomethyl)phenol
• CAS: 60365-79-9
• 化学式: C₁₆H₂₈N₂O
• 分子量: 264.411
• InChiKey: QJQBYNFARUROBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三乙基硼 、 2,6-bis-diethylaminomethyl-phenol 在 pivalic acid 作用下， 以 甲苯 为溶剂， 以65%的产率得到8-((diethylamino)methyl)-2,2,3,3-tetraethyl-3,4-dihydro-2H-2l4-benzo[e][1,3,2]oxazaborinin-3-ium
  参考文献：
  名称：

  Synthesis and spectroscopic studies on the base-stabilized aryloxyboron derivatives BX2{2-(NMe2CH2)OC6H4}, BX2{2-(NEt2CH2)OC6H4} and BX2{2,6-(NEt2CH2)2OC6H3}, (X=Cl, Et, H) and molecular structures of BCl2{2-(NEt2CH2)2OC6H4} and [BCl2{2-NHEt2CH2-6-(NEt2CH2)OC6H3}]Cl

  摘要：

  1-HO-2-(NMe2CH2)C6H4 (1a), 1-HO-2-(NEt2CH2)C6H4 (1b) and 1-HO-2,6-(NEt2CH2)(2)C6H3 (1c) reacted with BuLi to give the lithium salts 1-LiO-2-(NMe2CH2)C6H4 (2a) and 1-LiO-2,6-(NEt2CH2)(2)C6H3 (2c) or the phenol adducts [{1-LiO-2- (NR2CH2)C6H4}(2){1-HO-2-(NR2CH2)C6H4}] (R = Me (3a), Et (3b)). The phenol derivatives 1a-c reacted with BEt3 or BH3. thf with elimination of EtH or H-2 to give BX2 {2-(NMe2CH2)OC6H4} (X = Et (4a). H (5a)), BX2 {2-(NEt2CH2)OC6H4} (X = Et (4b), H (5b)) and BX2(2,6-(NEt2CH2)(2)OC6H3} (X=Et (4c), H (5c)). The reaction of 2a and 3b with BCl3 in toluene yielded BCl2 {2-(NMe2CH2)OC6H4} (6a) and BCl2{2-(NEt2CH2)OC6H4) (6b), while 2c afforded a mixture of BCl2{2,6-(NEt2CH2)(2)OC6H3} (6c) and BCl2{2-N(BCl3)Et2CH2-6-(NEt2CH2)OC6H3} (6c . BCl3). Treatment of this mixture with [PPh4]Cl gave [BCl2{2-NHEt2CH2-6-(NEt2CH2)OC6H3}]Cl (6c . HCl). The HCl-free product 6c was obtained from 6c . HCl and NaH. Compounds 2-6 and 6c . HCl were characterized spectroscopically (NMRI, IR), 5a and 6a-c also by MS, and crystal structures were determined for 6b and 6c . HCl. The borane derivatives 4-6 exhibit dynamic behavior in solution (ring opening and ring inversion), which was studied by VT H-1 NMR spectroscopy. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0277-5387(01)00746-x
• 作为产物：
  描述：

  聚合甲醛 、 二乙胺 、 苯酚 在 水 作用下， 生成 o-dimethylaminomethylphenol 、 2,6-bis-diethylaminomethyl-phenol
  参考文献：
  名称：

  The Condensation of Diethylamine and Formaldehyde with Phenol, o-, m- and p- Cresols¹

  摘要：

  DOI：

  10.1021/ja01227a031

文献信息

• Age resisting vulcanized rubber product
  申请人：RUBBER SERVICE LAB CO

  公开号：US01899426A1

  公开（公告）日：1933-02-28
• Rubber Serv. Labor. Co, Chemisches Zentralblatt, 1933, vol. 104, # I, p. 3637
  作者：Rubber Serv. Labor. Co

  DOI：——

  日期：——
• US4215229A
  申请人：——

  公开号：US4215229A

  公开（公告）日：1980-07-29
• US4322304A
  申请人：——

  公开号：US4322304A

  公开（公告）日：1982-03-30
• Synthesis and spectroscopic studies on the base-stabilized aryloxyboron derivatives BX2{2-(NMe2CH2)OC6H4}, BX2{2-(NEt2CH2)OC6H4} and BX2{2,6-(NEt2CH2)2OC6H3}, (X=Cl, Et, H) and molecular structures of BCl2{2-(NEt2CH2)2OC6H4} and [BCl2{2-NHEt2CH2-6-(NEt2CH2)OC6H3}]Cl
  作者：Rainer Papp、Joachim Sieler、Evamarie Hey-Hawkins

  DOI：10.1016/s0277-5387(01)00746-x

  日期：2001.4

  1-HO-2-(NMe2CH2)C6H4 (1a), 1-HO-2-(NEt2CH2)C6H4 (1b) and 1-HO-2,6-(NEt2CH2)(2)C6H3 (1c) reacted with BuLi to give the lithium salts 1-LiO-2-(NMe2CH2)C6H4 (2a) and 1-LiO-2,6-(NEt2CH2)(2)C6H3 (2c) or the phenol adducts [1-LiO-2- (NR2CH2)C6H4}(2)1-HO-2-(NR2CH2)C6H4}] (R = Me (3a), Et (3b)). The phenol derivatives 1a-c reacted with BEt3 or BH3. thf with elimination of EtH or H-2 to give BX2 2-(NMe2CH2)OC6H4} (X = Et (4a). H (5a)), BX2 2-(NEt2CH2)OC6H4} (X = Et (4b), H (5b)) and BX2(2,6-(NEt2CH2)(2)OC6H3} (X=Et (4c), H (5c)). The reaction of 2a and 3b with BCl3 in toluene yielded BCl2 2-(NMe2CH2)OC6H4} (6a) and BCl22-(NEt2CH2)OC6H4) (6b), while 2c afforded a mixture of BCl22,6-(NEt2CH2)(2)OC6H3} (6c) and BCl22-N(BCl3)Et2CH2-6-(NEt2CH2)OC6H3} (6c . BCl3). Treatment of this mixture with [PPh4]Cl gave [BCl22-NHEt2CH2-6-(NEt2CH2)OC6H3}]Cl (6c . HCl). The HCl-free product 6c was obtained from 6c . HCl and NaH. Compounds 2-6 and 6c . HCl were characterized spectroscopically (NMRI, IR), 5a and 6a-c also by MS, and crystal structures were determined for 6b and 6c . HCl. The borane derivatives 4-6 exhibit dynamic behavior in solution (ring opening and ring inversion), which was studied by VT H-1 NMR spectroscopy. (C) 2001 Elsevier Science Ltd. All rights reserved.