4-tert-butyl-2-(morpholin-4-ylmethyl)phenol | 25543-96-8

• 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: 4-tert-butyl-2-(morpholin-4-ylmethyl)phenol
• 英文别名: 4-(tert-butyl)-2-(morpholinomethyl)phenol；4-(1,1-dimethylethyl)-2-(4-morpholinylmethyl)-phenol
• CAS: 25543-96-8
• 化学式: C₁₅H₂₃NO₂
• 分子量: 249.353
• InChiKey: CHHOCJPVKSWIAO-UHFFFAOYSA-N

物化性质

• 熔点：
  75-78 °C
• 沸点：
  351.3±37.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-tert-butyl-2-(morpholin-4-ylmethyl)phenol 在 盐酸 、 potassium iodate 、 sodium iodide 作用下， 反应 0.07h， 以69%的产率得到[123I]-N-(5-tert-butyl-2-hydroxyphenyl-3-iodo)methylmorpholine
  参考文献：
  名称：

  Synthesis, attempted kinetic resolution and evaluation of [123I]-MK-447 analogues as inflammation radiopharmaceuticals

  摘要：

  The non-steroidal anti-inflammatory agent 2-amino-methyl-4-tert-butyl-6-iodophenol hydrochloride (MK-447) and some of its analogues were labelled with I-123 and tested in an inflamed rat-paw model. Even though MK-447 has a significant anti-inflammatory activity, and a 2.3 ratio for inflamed site over muscle, its usefullness for scintigraphic detection of inflammation is hindered by its high uptake in the skin. The kinetic resolution of diastereomeric products with chiral dienyl iron complexes was unsuccessful as the signals from the respective H-1 and C-13 NMR spectra were coincident.

  DOI：

  10.1002/(sici)1099-1344(199709)39:9<711::aid-jlcr22>3.0.co;2-a
• 作为产物：
  描述：

  吗啉 、 聚合甲醛 、 4-叔丁基苯酚 在 zinc(II) oxide 、 四丁基溴化铵 作用下， 反应 0.17h， 以93%的产率得到4-tert-butyl-2-(morpholin-4-ylmethyl)phenol
  参考文献：
  名称：

  纳米ZnO-TBAB为非均相催化介质的某些多酚化合物的合成及抑菌活性

  摘要：

  简介：曼尼希反应是三组分缩合反应的典型例子，曼尼希碱的化学性质一直是研究人员寻找的问题。在这里，描述了一种合成一些简单酚类新曼尼希衍生物的有效方法。方法：在该程序中，在不同的酚，仲胺和多聚甲醛之间进行了微波辅助的无溶剂缩合。反应在催化量的纳米ZnO和四丁基溴化铵（TBAB）的存在下进行，产率很高。合成了十个新化合物（A 1 -A 10）。所有新化合物的化学结构均通过不同的光谱方法确认。我们优化了不同条件下的化学反应。优化反应是在不同的无机氧化物，不同量的TBAB和不同溶剂的存在下进行的。催化量和无溶剂条件下的纳米ZnO和TBAB是最佳条件。筛选所有合成的化合物的抗菌活性。按照CLSI的建议，通过肉汤微稀释法评估了合成化合物对某些念珠菌，花丝真菌，革兰氏阳性和革兰氏阴性细菌的抗真菌和抗菌活性。结果：结果表明化合物A 2，A 3和A 4对大多数测试的念珠菌属和化合物A 5和A 7的抗副枝念珠菌

  DOI：

  10.2174/1570178617999200517131353

文献信息

• 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。
• Synthesis of symmetrical chromeno[2,3-b]chromenes on the basis of о-quinone methides and 1,1-bis(morpholino)ethene
  作者：Vitaly A. Osyanin、Dmitry V. Osipov、Maxim R. Demidov、Pavel E. Krasnikov、Yuri N. Klimochkin

  DOI：10.1007/s10593-018-2211-4

  日期：2017.12

  The reaction of 1,1-bis(morpholino)ethene with precursors of о-quinone methides derived from Mannich bases of phenols and 2-naphthols provided a series of chromeno[2,3-b]chromenes. The cascade process included a hetero-Diels–Alder reaction between о-quinone methide and ketenaminal, elimination of secondary amine, and [4+2] cycloaddition between о-quinone methide and the chromene intermediate.

  的1,1-双（吗啉代）乙烯与前体反应о由酚类和2-萘酚的曼尼希碱衍生-quinone甲基化物提供了一系列的色烯并[2,3-的b ]吡喃。级联过程之间包含一个杂Diels-Alder反应о -quinone甲基化物和ketenaminal，消除仲胺，和[4 + 2]环加成之间о -quinone甲基化物和色烯中间体。
• Imine Compound
  申请人：Saito Shiuji

  公开号：US20080312435A1

  公开（公告）日：2008-12-18

  An imine compound represented by the formula: wherein A represents a heterocyclic group; R 1 , R 2 , an R 3 each represent a hydrogen atom, a halogen atom, a C 1-10 alkyl group optionally substituted with an aryl group(s) substituted with a halogen atom(s), a C 3-10 cycloalkyl group, a C 1-6 haloalkyl group, a C 1-10 alkoxy group, etc.; R 4 represents an optionally substituted C 1-10 alkyl, C 2-6 alkenyl, or aryl group; R 5 represents a hydrogen atom, a C 1-10 alkoxy group, a C 1-6 haloalkyl group, an optionally substituted C 1-10 alkyl or C 2-6 alkenyl group, an optionally substituted aryl or heterocyclic group, etc.; W represents —CO—, —CO—CO—, —CO—NH—, —CS—NH—, or —SO 2 —, or a cannabinoid-receptor agonist comprising said imine compound as an active ingredient. The imine compound of the present invention has a cannabinoid-receptor agonist effect, and is useful as a therapeutic or prophylactic drug for pains and autoimmune diseases.

  一种以以下式表示的亚胺化合物：其中A代表杂环基团；R1、R2和R3分别表示氢原子、卤素原子、C1-10烷基，该烷基可选地取代有芳基，所述芳基取代有卤素原子，C3-10环烷基，C1-6卤代烷基，C1-10烷氧基等；R4表示可选地取代的C1-10烷基，C2-6烯基或芳基；R5表示氢原子，C1-10烷氧基，C1-6卤代烷基，可选地取代的C1-10烷基或C2-6烯基，可选地取代的芳基或杂环基团等；W表示—CO—，—CO—CO—，—CO—NH—，—CS—NH—或—SO2—，或以该亚胺化合物为活性成分的大麻素受体激动剂。本发明的亚胺化合物具有大麻素受体激动剂作用，可用作治疗或预防疼痛和自身免疫性疾病的药物。
• Regioselective Mannich Reaction of Phenols under High Pressure Using Dichloromethane as C1 Unit
  作者：Kiyoshi Matsumoto、Kouta Joho、Seisuke Mimori、Hirokazu Iida、Hiroshi Hamana、Akikazu Kakehi

  DOI：10.3987/com-08-s(n)111

  日期：——

  Regioselectivity in Mannich reaction of 4-, 3-, and 2-substituted phenols with typical heterocyclic amines are investigated under reaction conditions developed by Lis. Phenol and 4-alkyl, and 4-chlorophenols in the title reaction predominantly gave the corresponding 2-(aminometllyl)phenols, while 4-methoxyphenol afforded, in addition to the mono(aminomethyl) phenols, a considerable amount of the bis adducts. Peculiarly enough, 3-methylphenol with amines afforded 3-methyl-4-(aminomethyl) phenols whereas 2-methylphenol produced 2-methyl-6-(aminomethyl)phenols.
• Eco-Friendly Synthesis of Novel Lariat Ethers via Mannich Reaction under Solventless Conditions
  作者：Hashem Sharghi、Reza Khalifeh

  DOI：10.3987/com-07-11044

  日期：——

  An expeditious solventless synthesis of novel lariat ethers using calcium oxide (CaO) via Mannich reaction are herein described. This methodology eliminates the use of excess of solvent during the course of reaction. The reaction time is brought down from hours to minutes (20-30 minutes) along with yield enhancement. The CaO powder can be reused up to three times after simple washing with acetone.