p-(N,N-dimethylamino)phenyl-1,2-ethanediol | 149302-71-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: p-(N,N-dimethylamino)phenyl-1,2-ethanediol
• 英文别名: (+/-)-1-<4-(dimethylamino)phenyl>-1,2-ethanediol；1-(4-(Dimethylamino)phenyl)ethane-1,2-diol；1-[4-(dimethylamino)phenyl]ethane-1,2-diol
• CAS: 149302-71-6
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: LVMUWXSRVYKJPA-UHFFFAOYSA-N

物化性质

• 沸点：
  353.1±32.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  p-(N,N-dimethylamino)phenyl-1,2-ethanediol 在 4-二甲氨基吡啶 、 水 、 氧气 、 Selectfluor 、 10-甲基-9-均三甲苯基吖啶高氯酸盐 作用下， 以 乙腈 为溶剂， 以74 %的产率得到4-二甲氨基苯甲酸
  参考文献：
  名称：

  腈、醇和胺的 C(sp3)−C 和 C(sp3)−N 键的无金属可见光诱导氧化裂解

  摘要：

  这项工作提出了使用 Acr + -Mes/Selectflu/DMAP 系统和 O 对腈、醇（二醇）和胺的无张力 C−C(sp 3 ) 和 C−N(sp 3 ) 键进行可见光介导的氧化裂解2作为氧化剂。

  DOI：

  10.1002/chem.202303295
• 作为产物：
  描述：

  4-二甲基氨基苯乙烯 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 反应 3.5h， 以84%的产率得到p-(N,N-dimethylamino)phenyl-1,2-ethanediol
  参考文献：
  名称：

  Cyclocondensation of oxalyl chloride with 1,2-glycols

  摘要：

  Oxalyl chloride reacts with a wide range of acyclic 1,2-glycols 1 in the presence of triethylamine to produce 1,3-dioxolan-2-ones 3 together with 1,4-dioxane-2,3-diones 2. Ethylene glycol (1d), monosubstituted ethylene glycols 1e, j-1, and erythro-1,2-disubstituted ethylene glycols 1f, m,o provide the cyclic carbonates 3 as the minor products, while the threo-compounds 1g, i, n,p,q and pinacol (1h) afford 3 as the main products. The formation of 3 may be rationalized in terms of stereoelectronically controlled cleavage of the conjugate base 17- of the tetrahedral intermediates. The rate for the conformational change of 17- into 18- and the equilibrium constant between these conformers are proposed to be the major factors affecting the reaction pattern.

  DOI：

  10.1016/s0040-4020(01)81546-5

文献信息

• Formation of cyclic carbonates in the reactions of 1,2-glycols with oxalyl chloride.
  作者：Taisuke ITAYA、Takehiko IIDA、Hiromi EGUCHI

  DOI：10.1248/cpb.41.408

  日期：——

  Oxalyl chloride reacts with a wide range of 1, 2-glycols in the presence of triethylamine to produce 1, 3-dioxolan-2-ones together with 1, 4-dioxane-2, 3-diones; the ratio of the products largely depends on the structure of the 1, 2-glycol. The formation of the cyclic carbonates may be rationalized in terms of stereoelectronically controlled cleavage of the tetrahedral intermediates.

  草酰氯在三乙胺存在下与广泛的1, 2-二醇反应，生成1, 3-二恶烷-2-酮和1, 4-二恶烷-2, 3-二酮；产物的比例很大程度上取决于1, 2-二醇的结构。环状碳酸酯的形成可以用四面体中间体的手性电子控制断裂来合理化。
• 4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamides as antiviral agents
  申请人：Schnute Edward Mark

  公开号：US20050004161A1

  公开（公告）日：2005-01-06

  The invention provides a compound of formula I: wherein A, B, R 1 , R 2 , R 3 , and R 4 are as defined in the specification. The compounds of the present invention are useful for treating viral infections, in particular a herpesviral infection.

  该发明提供了化合物I的结构，其中A、B、R1、R2、R3和R4如规范中定义。本发明的化合物对治疗病毒感染，特别是单纯疱疹病毒感染，具有实用价值。
• Katritzky, Alan R.; Galuszka, Barbara; Rachwal, Stanislaw, Organic Preparations and Procedures International, 1993, vol. 25, # 5, p. 557 - 562
  作者：Katritzky, Alan R.、Galuszka, Barbara、Rachwal, Stanislaw、Lynch, Doreen

  DOI：——

  日期：——
• Cyclocondensation of oxalyl chloride with 1,2-glycols
  作者：Takehiko Iida、Taisuke Itaya

  DOI：10.1016/s0040-4020(01)81546-5

  日期：1993.1

  Oxalyl chloride reacts with a wide range of acyclic 1,2-glycols 1 in the presence of triethylamine to produce 1,3-dioxolan-2-ones 3 together with 1,4-dioxane-2,3-diones 2. Ethylene glycol (1d), monosubstituted ethylene glycols 1e, j-1, and erythro-1,2-disubstituted ethylene glycols 1f, m,o provide the cyclic carbonates 3 as the minor products, while the threo-compounds 1g, i, n,p,q and pinacol (1h) afford 3 as the main products. The formation of 3 may be rationalized in terms of stereoelectronically controlled cleavage of the conjugate base 17- of the tetrahedral intermediates. The rate for the conformational change of 17- into 18- and the equilibrium constant between these conformers are proposed to be the major factors affecting the reaction pattern.
• Metal‐Free Visible‐Light Induced Oxidative Cleavage of C(sp³)−C, and C(sp³)−N Bonds of Nitriles, Alcohols, and Amines
  作者：Ishani Borthakur、Abhisek Joshi、Saloni Kumari、Sabuj Kundu

  DOI：10.1002/chem.202303295

  日期：2024.3.7

  This work presents a visible-light mediated oxidative cleavage of unstrained C−C(sp3) and C−N(sp3) bonds of nitriles, alcohols (diols), and amines using Acr+-Mes/Selectfluor/DMAP system and O2 as the oxidant.

  这项工作提出了使用 Acr + -Mes/Selectflu/DMAP 系统和 O 对腈、醇（二醇）和胺的无张力 C−C(sp 3 ) 和 C−N(sp 3 ) 键进行可见光介导的氧化裂解2作为氧化剂。