o-dimethylaminomethylphenol | 4992-02-3

• 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: o-dimethylaminomethylphenol
• 英文别名: 2-diethylaminomethylphenol；o-CRESOL, alpha-(DIETHYLAMINO)-；2-(diethylaminomethyl)phenol
• CAS: 4992-02-3
• 化学式: C₁₁H₁₇NO
• 分子量: 179.262
• InChiKey: IGXXOUGMPVOZFH-UHFFFAOYSA-N

物化性质

• 沸点：
  63-67 °C(Press: 1-2 Torr)
• 密度：
  0.9780 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  o-dimethylaminomethylphenol 在 哌啶 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 2,4-diamino-5H-chromeno[2,3-b]pyridine-3-carbonitrile
  参考文献：
  名称：

  Aminocyanopyridine inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)

  摘要：

  A class of inhibitors of mitogen-activated protein kinase-activated protein kinase 2 (MK-2) was discovered. These compounds have demonstrated activity against the enzyme with IC50 values as low as 130 nM and suppress the expression of TNFα in U937 cells. These represent the first small molecule inhibitors of MK-2 to be reported. © 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.067
• 作为产物：
  描述：

  diethyl-2-(methoxybenzyl)amine 在 nickel dichloride 、 锌 作用下， 以 xylene 为溶剂， 反应 72.0h， 以51%的产率得到o-dimethylaminomethylphenol
  参考文献：
  名称：

  镍/锌介导的烷基芳基醚的烷基碳氧键裂解

  摘要：

  在中性条件下，在对二甲苯中用氯化镍 (II) 和锌处理，可以有效地裂解带有合适配位点的烷基芳基醚的烷基碳-氧键。

  DOI：

  10.1081/scc-100103322
• 作为试剂：
  描述：

  4-nitrophenyl bis(chloromethyl)phosphinate 在 sodium nitrate 、 o-dimethylaminomethylphenol 作用下， 以 乙醇 、 水 为溶剂， 生成 di(chloromethyl)phosphinic acid
  参考文献：
  名称：

  Reactivity of 2-diethylaminomethylphenol and its copper(II) complex in the reaction with 4-nitrophenylbis(chloromethyl)-phosphinate

  摘要：

  The kinetics of reactions of 2-diethylaminomethylphenol (I) and its Cu2+ complex (with a metal: ligand composition of 1:2) (II) with 4-nitrophenylbis(chloromethyl)-phosphinate have been studied in aqueous-ethanolic media (10-70 vol. % ethanol); bimolecular rate constants have been calculated for the reactions of different forms of compound (I) and complex (II). It was shown that compound (I) in aqueous-ethanolic media is a nucleophilic catalyst for hydrolysis of 4-nitrophenylbis(chloromethyl)-phosphinate. The reactivity of complex (II) is an order of magnitude greater than that of the zwitterion form of the ligand which exists in the same range of pH 7-9.

  DOI：

  10.1007/bf00957979

文献信息

• Reactivity of new precursors of quinone methides
  作者：Bernard Loubinoux、Joseph Miazimbakana、Philippe Gerardin

  DOI：10.1016/s0040-4039(00)99619-9

  日期：1989.1

  The azidomethylene protecting group allows the synthesis of unstable phenolic compounds which are used as quinone methide precursors in the alkylations of alcohols, phenols, azide, thiophenol, amines, enols and enolates.

  叠氮基亚甲基保护基团允许合成不稳定的酚类化合物，在醇，酚，叠氮化物，硫酚，胺，烯醇和烯醇化物的烷基化中用作醌甲基化物前体。
• The modified-Mannich reaction: Conversion of arylboronic acids and subsequent coupling with paraformaldehyde and amines toward the one-pot synthesis of Mannich bases and benzoxazines
  作者：Juan Liu、Gaoqing Yuan

  DOI：10.1016/j.tetlet.2017.02.081

  日期：2017.4

  A modified Mannich reaction has been developed for the synthesis of Mannich bases and benzoxazines via the oxidative hydroxylation of arylboronic acids and subsequent coupling with paraformaldehyde and amines in one pot. This modified Mannich reaction is easily carried out to afford the target products in good to excellent yields and tolerates a variety of functional groups.

  已开发出一种改良的曼尼希反应，用于通过芳基硼酸的氧化羟基化反应，随后在一个罐中与多聚甲醛和胺偶联来合成曼尼希碱和苯并恶嗪。容易进行这种修饰的曼尼希反应，以高至优异的产率提供目标产物，并能耐受多种官能团。
• Aminoborohydrides. 3. A facile reduction of tertiary amides to the corresponding amines and alcohols in high purity using lithium aminoborohydrides. Sterically controlled selective CN or CO bond cleavage
  作者：Gary B. Fisher、Joseph C. Fuller、John Harrison、Christian T. Goralski、Bakthan Singaram

  DOI：10.1016/s0040-4039(00)77498-3

  日期：1993.2

  Lithium aminoborohydrides (LiABH3), obtained by the reaction of n-BuLi with amine-boranes, are powerful reducing agents for the reduction of tertiary amides to the corresponding amines or alcohols. Lithium pyrrolidinoborohydride (LiPyrrBH3) and lithium diisopropylaminoborohydride (LiH3BN(i-Pr)2) reduce both aliphatic and aromatic tertiary amides to give either the corresponding alcohol or amine, depending

  通过n-BuLi与胺-硼烷反应获得的氨基硼氢化锂（LiABH 3）是有效的还原剂，可将叔酰胺还原为相应的胺或醇。锂pyrrolidinoborohydride（LiPyrrBH 3）和锂diisopropylaminoborohydride（LIH 3 BN（I-PR）2）降低脂族和芳族叔胺酰胺，得到任一相应的醇或胺，取决于叔酰胺的空间要求和LiABH 3中使用。从该方法得到的胺和醇的收率范围从非常好到基本上定量。
• SMALL MOLECULES FOR IMMUNOGENIC TREATMENT OF CANCER
  申请人：Capten Therapeutics Inc.

  公开号：US20190062272A1

  公开（公告）日：2019-02-28

  The present invention relates to new compounds for immunogenic treatment of cancer. The compounds can be administered as a single agent or in combination with an anticancer drug including modulators of other immune pathways, especially immune checkpoint inhibitors that target CTLA-4, PD-1, and PD-L1 proteins. The compounds can produce neoantigens through irreversible protein binding in cancer cells and generate immune response.

  本发明涉及用于免疫治疗癌症的新化合物。这些化合物可以作为单一药剂或与抗癌药物一起给予，包括调节其他免疫途径的调节剂，尤其是针对CTLA-4、PD-1和PD-L1蛋白的免疫检查点抑制剂。这些化合物可以通过在癌细胞中进行不可逆蛋白结合产生新抗原，并引发免疫反应。
• Anionic ortho-Fries Rearrangement, a Facile Route to Arenol-Based Mannich Bases
  作者：Petros Tsoungas、Nikos Assimomytis、Yiannis Sariyannis、Georgios Stavropoulos、George Varvounis、Paul Cordopatis

  DOI：10.1055/s-0029-1217991

  日期：2009.10

  and 1-naphthol-based carbamates undergo the anionic ortho-Fries rearrangement to their corresponding amides. Bulky substitution at position 8 of 1-naphthol-based carbamates makes the rearrangement an exclusive reaction, even at -90 °C, un- der a variety of conditions. The amides can be efficiently reduced to the corresponding Mannich bases. A novel route to 7-((dialkylami- no)methyl)-8-hydroxy-1-naphthaldehydes

  苯酚和基于 1-萘酚的氨基甲酸酯经过阴离子邻位-弗里斯重排为其相应的酰胺。1-萘酚基氨基甲酸酯在 8 位的大量取代使重排成为一种独特的反应，即使在 -90 °C 下，在各种条件下也是如此。酰胺可以有效地还原为相应的曼尼希碱。提出了一种制备 7-((二烷基氨基) 甲基)-8-羟基-1-萘醛的新途径。