5-((4-methoxybenzyl)oxy)-4-oxo-4H-pyran-2-carbaldehyde | 898045-03-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-((4-methoxybenzyl)oxy)-4-oxo-4H-pyran-2-carbaldehyde
• 英文别名: 5-[(4-methoxyphenyl)methoxy]-4-oxopyran-2-carbaldehyde
• CAS: 898045-03-9
• 化学式: C₁₄H₁₂O₅
• 分子量: 260.246
• InChiKey: PKBSOTAXPLGYGE-UHFFFAOYSA-N

物化性质

• 沸点：
  504.1±50.0 °C(predicted)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-((4-methoxybenzyl)oxy)-4-oxo-4H-pyran-2-carbaldehyde 在 ammonium hydroxide 、 sodium chlorite 、 氨基磺酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 N-(1-azabicyclo[2.2.2]octan-4-ylmethyl)-5-[(4-methoxyphenyl)methoxy]-4-oxo-1H-pyridine-2-carboxamide
  参考文献：
  名称：

  CEPHEM COMPOUND HAVING PSEUDO-CATECHOL GROUP

  摘要：

  该化合物的化学式为：其中X为—N═、—CH═或类似基团；W为—CH2—或类似基团；U为—S—或类似基团；R1和R2各自独立地为氢、卤素、选择性取代的低碳基或类似基团；Q为单键或类似键；R3为氢或类似基团；环A为一个6元芳香杂环基团，具有1-3个氮原子；每个R4独立地为氢、卤素或类似基团；m为0到2的整数；G为—C(═O)—或类似基团；D为单键、—NH—或类似基团；E为一个环状季铵基团，或者是在7侧链上的氨基处的酯、保护化合物、药学上可接受的盐或其溶剂化物。

  公开号：

  US20130079319A1
• 作为产物：
  描述：

  曲酸 在 manganese(IV) oxide 、 potassium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 80.0h， 生成 5-((4-methoxybenzyl)oxy)-4-oxo-4H-pyran-2-carbaldehyde
  参考文献：
  名称：

  Identification of 2-subsituted benzothiazole derivatives as triple-functional agents with potential for AD therapy

  摘要：

  一系列2-取代苯并噻唑衍生物被设计并合成为潜在的AD治疗药物。

  DOI：

  10.1039/c5ra25788c

文献信息

• Synthesis of Tyrosinase Inhibitory Kojic Acid Derivative
  作者：Yong Sup Lee、Jang Hyun Park、Min Hwan Kim、Seon Hee Seo、Hyoung Ja Kim

  DOI：10.1002/ardp.200500213

  日期：2006.3

  Kojic acid derivative 2 was synthesized by joining two pyrone rings through an ethylene linkage by Horner‐Emmons reaction of phosphonate 6 with aldehyde 7. The intermediates 6 and 7 were derived from kojic acid. The tyrosinase inhibitory activity of 2 was about 8 times more potent (IC50 = 3.63 μM) than that of kojic acid (IC50 = 30.61 μM). Compound 2 also exhibited potent melanin synthesis inhibitory

  通过膦酸酯 6 与醛 7 的霍纳-埃蒙斯反应，通过乙烯键连接两个吡喃酮环合成曲酸衍生物 2。中间体 6 和 7 衍生自曲酸。2 的酪氨酸酶抑制活性 (IC50 = 3.63 μM) 比曲酸 (IC50 = 30.61 μM) 强约 8 倍。化合物 2 还表现出有效的黑色素合成抑制活性（5 μg 时抑制率为 19.53%），表明曲酸的两个吡喃酮环通过合适的接头连接可以是鉴定有效酪氨酸酶抑制剂的有用策略。
• Synthesis of tyrosinase inhibitory (4-oxo-4H-pyran-2-yl)acrylic acid ester derivatives
  作者：Soo Sung Kang、Hyoung Ja Kim、Changbae Jin、Yong Sup Lee

  DOI：10.1016/j.bmcl.2008.10.119

  日期：2009.1

  Melanogenesis is a physiological process that results in the production of melanin pigment. However, excessive accumulations of epidermal pigmentation can cause various hyperpigmentary disorders such as, melasma and age spots. Kojic acid and hydroxylated cinnamic acid derivatives are known to inhibit tyrosinase, a key component of melanin biosynthesis. Pyronyl-acrylic acid esters 3a-i, which share structural features of kojic acid and hydroxylated cinnamic acid, were prepared and their abilities to inhibit tyrosinase and melanin production were evaluated. Of the esters synthesized, 3e and 3h, which derived from diethylene glycol moieties were found to inhibit melanin production by ca. 20% at 20 mu g/ml, whereas kojic acid at 200 mu g/ml inhibited melanin production by 15.8%. (C) 2008 Elsevier Ltd. All rights reserved.
• US8883773B2
  申请人：——

  公开号：US8883773B2

  公开（公告）日：2014-11-11
• Identification of 2-subsituted benzothiazole derivatives as triple-functional agents with potential for AD therapy
  作者：Liu Jiang、Minkui Zhang、Li Tang、Qinjie Weng、Yanhong Shen、Yongzhou Hu、Rong Sheng

  DOI：10.1039/c5ra25788c

  日期：——

  A series of 2-subsituted benzothiazole derivatives were designed and synthesized as MDTLs for potential AD therapy.

  一系列2-取代苯并噻唑衍生物被设计并合成为潜在的AD治疗药物。
• CEPHEM COMPOUND HAVING PSEUDO-CATECHOL GROUP
  申请人：Yamawaki Kenji

  公开号：US20130079319A1

  公开（公告）日：2013-03-28

  A compound of the formula: wherein X is —N═, —CH═, or the like; W is —CH 2 — or the like; U is —S— or the like; R 1 and R 2 are each independently hydrogen, halogen, optionally substituted lower alkyl, or the like; Q is a single bond or the like; R 3 is hydrogen or the like; Ring A is a 6-membered aromatic heterocyclic group having 1-3 nitrogen atoms; each R 4 is independently hydrogen, halogen, or the like; m is an integer from 0 to 2; G is —C(═O)— or the like; D is a single bond, —NH—, or the like; and E is a cyclic quaternary ammonium group, or an ester, a protected compound at the amino on the ring in the 7-side chain, a pharmaceutically acceptable salt, or a solvate thereof.

  该化合物的化学式为：其中X为—N═、—CH═或类似基团；W为—CH2—或类似基团；U为—S—或类似基团；R1和R2各自独立地为氢、卤素、选择性取代的低碳基或类似基团；Q为单键或类似键；R3为氢或类似基团；环A为一个6元芳香杂环基团，具有1-3个氮原子；每个R4独立地为氢、卤素或类似基团；m为0到2的整数；G为—C(═O)—或类似基团；D为单键、—NH—或类似基团；E为一个环状季铵基团，或者是在7侧链上的氨基处的酯、保护化合物、药学上可接受的盐或其溶剂化物。