3-(4-吗啉基)苯甲醇 | 145127-38-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 中文名称: 3-(4-吗啉基)苯甲醇
• 中文别名: (3-吗啉苯基)甲醇
• 英文名称: (3-morpholinophenyl)methanol
• 英文别名: (3-morpholin-4-ylphenyl)methanol
• CAS: 145127-38-4
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: MXBVALXTJZMIJB-UHFFFAOYSA-N

物化性质

• 熔点：
  51 °C
• 沸点：
  379.6±42.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  3-(4-吗啉基)苯甲醇 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 二甲基硫 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 6.5h， 生成 2-(3,4-Dihydroxyphenyl)-6-[(3-morpholin-4-ylphenyl)methylsulfanyl]-4-oxo-2,3-dihydro-1,3-thiazine-5-carbonitrile
  参考文献：
  名称：

  Structure–Activity Analysis and Cell-Based Optimization of Human Galactokinase Inhibitors

  摘要：

  Classic galactosemia is a rare human disease associated with the accumulation of a toxic level of galactose-1-phosphate (gal-1P) caused by the inherited deficiency of galactose-1-phosphate uridyltransferase (GALT) activity. To reduce the toxic level of gal-1P in patients, we have identified, via high-throughput screening, over 200 small molecule GALK inhibitors. We selected a 4-oxo-3,4-dihydro-2H-1,3-thiazine-5-carbonitrile scaffold for further structure-activity relationships characterization, lead optimization with regards to potency, and efficacy to reduce gal-1P accumulation in patient cells.

  DOI：

  10.1021/ml200131j
• 作为产物：
  描述：

  3-碘苯甲酸甲酯 在 sodium tetrahydroborate 、 copper(l) iodide 、 potassium carbonate 、 L-脯氨酸 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 为溶剂， 反应 10.0h， 生成 3-(4-吗啉基)苯甲醇
  参考文献：
  名称：

  Discovery of novel pyrrole-based scaffold as potent and orally bioavailable free fatty acid receptor 1 agonists for the treatment of type 2 diabetes

  摘要：

  The free fatty acid receptor 1 (FFA1) has gained significant interest as a novel antidiabetic target. Most of FFA1 agonists reported in the literature bearing a common biphenyl scaffold, which was crucial for toxicity verified by the researchers of Daiichi Sankyo. Herein, we describe the systematic exploration of non-biphenyl scaffold and further chemical modification of the optimal pyrrole scaffold. All of these efforts led to the identification of compound 11 as a potent and orally bioavailable FFA1 agonist without the risk of hypoglycemia. Further molecular modeling studies promoted the understanding of ligand-binding pocket and might help to design more promising FFA1 agonists. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.03.014

文献信息

• Palladium Catalysis Enables Benzylation of α,α‐Difluoroketone Enolates
  作者：Ming‐Hsiu Yang、Jordan R. Hunt、Niusha Sharifi、Ryan A. Altman

  DOI：10.1002/anie.201604149

  日期：2016.7.25

  A palladium‐catalyzed decarboxylative benzylation reaction of α,α‐difluoroketone enolates is reported, in which the key C(α)−C(sp3) bond is generated by reductive elimination from a palladium intermediate. The transformation provides convergent access to α‐benzyl‐α,α‐difluoroketone‐based products, and should be useful for accessing biological probes.

  据报道，钯催化的α，α-二氟酮烯酸酯的脱羧苄基化反应，其中关键的C（α）-C（sp 3）键是通过从钯中间体中进行还原性消除而生成的。这种转化提供了对基于α-苄基-α，α-二氟酮的产品的集中访问，并且对于访问生物探针应该是有用的。
• β‐Aryl Nitrile Construction<i>via</i>Palladium‐Catalyzed Decarboxylative Benzylation of α‐Cyano Aliphatic Carboxylate Salts
  作者：Rui Shang、Zheng Huang、Xiao Xiao、Xi Lu、Yao Fu、Lei Liu

  DOI：10.1002/adsc.201200383

  日期：2012.9.17

  The palladium‐catalyzed decarboxylative benzylation of α‐cyano aliphatic carboxylate salts with benzyl electrophiles was discovered. This reaction exhibits good functional group compatibility and proceeds under relatively mild conditions. A diverse range of quaternary, tertiary and secondary β‐aryl nitriles can be conveniently prepared by this method.

  发现了α-氰基脂肪族羧酸盐与苄基亲电试剂的钯催化脱羧苄基化反应。该反应表现出良好的官能团相容性，并且在相对温和的条件下进行。通过这种方法可以方便地制备各种范围的季，叔和仲β-芳基腈。
• [EN] HETEROCYCLYL PYRAZOLOPYRIMIDINE ANALOGUES AS JAK INHIBITORS<br/>[FR] ANALOGUES D'HÉTÉROCYCLYL PYRAZOLOPYRIMIDINE EN TANT QU'INHIBITEURS DE JAK
  申请人：CELLZOME LTD

  公开号：WO2011048082A1

  公开（公告）日：2011-04-28

  The present invention relates to compounds of formula (I) wherein X1 to X5, Y, Z1 to Z3, and R have the meaning as cited in the description and the claims. Said compounds are useful as JAK inhibitors for the treatment or prophylaxis of immunological, inflammatory, autoimmune, allergic disorders, and immunologically-mediated diseases. The invention also relates to pharmaceutical compositions including said compounds, the preparation of such compounds as well as the use as medicaments.

  本发明涉及式(I)的化合物，其中X1至X5，Y，Z1至Z3和R的含义如描述和权利要求中所述。所述化合物可用作JAK抑制剂，用于治疗或预防免疫、炎症、自身免疫、过敏性疾病和免疫介导性疾病。该发明还涉及包括所述化合物的药物组合物，以及制备这类化合物以及用作药物的用途。
• Combined KOH/BEt₃ Catalyst for Selective Deaminative Hydroboration of Aromatic Carboxamides for Construction of Luminophores
  作者：Wubing Yao、Jiali Wang、Aiguo Zhong、Jinshan Li、Jianguo Yang

  DOI：10.1021/acs.orglett.0c03033

  日期：2020.10.16

  amides into value-added amine products is a desirable but challenging transformation. Molecules containing iminodibenzyl motifs are prevalent in pharmaceutical molecules and functional materials. Here we established a combined KOH/BEt3 catalyst for deaminative hydroboration of acyl-iminodibenzyl derivatives, including nonheterocyclic carboxamides, to the corresponding amines. This novel transition-metal-free

  酰胺选择性催化C–N键裂解为增值胺产品是一种理想的但具有挑战性的转化。含有亚氨基二苄基基序的分子普遍存在于药物分子和功能材料中。在这里，我们建立了一种组合的KOH / BEt 3催化剂，用于将酰基-亚氨基二苄基衍生物（包括非杂环羧酰胺）进行脱氨基硼氢化成相应的胺。这种新颖的无过渡金属的方法也被用于氯米帕明和发光体的构建。
• [EN] NITROGEN-CONTAINING FUSED HETEROCYCLIC COMPOUNDS AND THEIR USE AS BETA AMYLOID PRODUCTION INHIBITORS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES CONDENSÉS CONTENANT DE L'AZOTE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE PRODUCTION DE LA BÊTA-AMYLOÏDE
  申请人：EISAI R&D MAN CO LTD

  公开号：WO2010098487A1

  公开（公告）日：2010-09-02

  A compound represented by the formula [I]: or a pharmacologically acceptable salt or ester thereof, wherein Ring A represents a five-membered aromatic heterocyclic group or the like fused with a non-aromatic ring group, which may be substituted, Ring B represents a phenyl group or the like which may be substituted, X1 represents a single bond or the like, R1 and R2 each represent a C1-6 alkyl group or the like, m represents an integer of 0 to 3, and n represents an integer of 0 to 2, is effective as a therapeutic agent for a disease caused by Aβ.

  化合物的分子式为[I]：或其药理学可接受的盐或酯，其中环A代表一个五元芳香杂环基团或类似于非芳香环基团的融合物，可以被取代，环B代表一个苯基或类似的基团，可以被取代，X1代表一个单键或类似物，R1和R2分别代表一个C1-6烷基基团或类似物，m表示0到3的整数，n表示0到2的整数，对由Aβ引起的疾病具有治疗作用。