(+/-)-2-(tetrahydropyran-2-ylmethoxy)ethanol | 100249-57-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (+/-)-2-(tetrahydropyran-2-ylmethoxy)ethanol
• 英文别名: 2-((tetrahydro-2H-pyran-2-yl)oxy)ethan-1-ol；2--aethanol；2-[(tetrahydro-2H-pyran-2-ylmethyl)oxy]ethanol；2-[(tetrahydro-2H-pyran-2-yl)methoxy]Ethanol；2-(oxan-2-ylmethoxy)ethanol
• CAS: 100249-57-8
• 化学式: C₈H₁₆O₃
• 分子量: 160.213
• InChiKey: BMZMZVWLLBPAJY-UHFFFAOYSA-N

物化性质

• 沸点：
  138-140 °C(Press: 30 Torr)
• 密度：
  1.030±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-2-(tetrahydropyran-2-ylmethoxy)ethanol 在 N-甲基吗啉 、 sodium azide 、 四丁基溴化铵 、 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 24.0h， 生成 (+/-)-N-<2-(tetrahydropyran-2-ylmethoxy)ethyl>-2-<4-(3-pyridylcarbonyl)phenyl>-4-oxazolecarboxamide
  参考文献：
  名称：

  Development of Dual-Acting Agents for Thromboxane Receptor Antagonism and Thromboxane Synthase Inhibition. 3. Synthesis and Biological Activities of Oxazolecarboxamide-Substituted ω-Phenyl-ω-(3-pyridyl)alkenoic Acid Derivatives and Related Compounds

  摘要：

  A novel series of oxazolecarboxamide-substituted omega-phenyl-omega-(3-pyridyl)alkenoic acid derivatives was discovered as potent dual-acting agents to block the TXA(2) receptor and to inhibit the thromboxane synthase (TRA/TSI). Synthesis, structure-activity relationship (SAR), and in vitro and in vivo pharmacology of this series of compounds are described. Modification of the series revolved around the oxazole moiety to increase the hydrophilicity of the compounds and to correlate the biological activity with lipophilicity of the compounds. The most potent in the series was (E)-7-[4-[4-[[(4-cyclohexylbutyl)amino]carbonyl]-2-oxazolyl]phenyl]-7-(3-pyridyl)hept-6-enoic acid (14) with K-d = 9.9 +/- 0.4 nM for the thromboxane receptor antagonism and IC50 = 55.0 +/- 17.9 nM for thromboxane synthase inhibition. The compound 14 was a selective TRA/TSI which exhibited desirable characteristics for oral activity, "shunt" effect to elevate PGI(2) level, and absence of agonist activity.

  DOI：

  10.1021/jm980173n
• 作为产物：
  描述：

  四氢吡喃-2-甲醇 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 (+/-)-2-(tetrahydropyran-2-ylmethoxy)ethanol
  参考文献：
  名称：

  Development of Dual-Acting Agents for Thromboxane Receptor Antagonism and Thromboxane Synthase Inhibition. 3. Synthesis and Biological Activities of Oxazolecarboxamide-Substituted ω-Phenyl-ω-(3-pyridyl)alkenoic Acid Derivatives and Related Compounds

  摘要：

  A novel series of oxazolecarboxamide-substituted omega-phenyl-omega-(3-pyridyl)alkenoic acid derivatives was discovered as potent dual-acting agents to block the TXA(2) receptor and to inhibit the thromboxane synthase (TRA/TSI). Synthesis, structure-activity relationship (SAR), and in vitro and in vivo pharmacology of this series of compounds are described. Modification of the series revolved around the oxazole moiety to increase the hydrophilicity of the compounds and to correlate the biological activity with lipophilicity of the compounds. The most potent in the series was (E)-7-[4-[4-[[(4-cyclohexylbutyl)amino]carbonyl]-2-oxazolyl]phenyl]-7-(3-pyridyl)hept-6-enoic acid (14) with K-d = 9.9 +/- 0.4 nM for the thromboxane receptor antagonism and IC50 = 55.0 +/- 17.9 nM for thromboxane synthase inhibition. The compound 14 was a selective TRA/TSI which exhibited desirable characteristics for oral activity, "shunt" effect to elevate PGI(2) level, and absence of agonist activity.

  DOI：

  10.1021/jm980173n

文献信息

• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2010018132A1

  公开（公告）日：2010-02-18

  Compounds of formula (I): wherein R1 is C1-6alkylamino, or C1-6alkoxy; m is an integer having a value of 2 or 3; n is an integer having a value of 0 to 3; p is an integer having a value of 1 or 2; and salts thereof are inducers of human interferon. Compounds which induce human interferon may be useful in the treatment of various disorders, for example the treatment of allergic diseases and other inflammatory conditions for example allergic rhinitis and asthma, the treatment of infectious diseases and cancer, and may also be useful as vaccine adjuvants.

  式(I)的化合物：其中R1是C1-6烷基氨基或C1-6烷氧基；m是一个值为2或3的整数；n是一个值为0至3的整数；p是一个值为1或2的整数；以及它们的盐是人类干扰素的诱导剂。诱导人类干扰素的化合物可能在治疗各种疾病中有用，例如治疗过敏性疾病和其他炎症性疾病，例如过敏性鼻炎和哮喘，治疗传染病和癌症，并且还可能作为疫苗佐剂有用。
• Red light-induced highly efficient aerobic oxidation of organoboron compounds using spinach as a photocatalyst
  作者：Peng Yan、Rong Zeng、Bo Bao、Xiu-Ming Yang、Lei Zhu、Bin Pan、Sheng-Li Niu、Xiao-Wei Qi、Yu-Long Li、Qin Ouyang

  DOI：10.1039/d2gc03055a

  日期：——

  A simple and general red light-induced oxidation of organoboron compounds to obtain hydroxyl has been developed with spinach as the photocatalyst in alcohol. This mild protocol shows broad substrate scope and provides a wide range of aliphatic alcohols and phenols in moderate to excellent yields. Notably, the robustness of this method is suitable for B(OH)2, Bpin, Bneo and BF3K substrates that respond

  已经开发了一种简单且通用的红光诱导有机硼化合物氧化以获得羟基，菠菜作为醇中的光催化剂。这种温和的协议显示了广泛的底物范围，并以中等至优异的产量提供了广泛的脂肪醇和酚。值得注意的是，该方法的稳健性适用于 B(OH) 2、Bpin、Bneo 和 BF 3对不同光（包括红色、蓝色和阳光）作出反应的 K 底物。更大规模的实验和绿色化学指标分析证明，这是一种稳健且绿色的方法，甚至可以仅使用厨房设备和配料进行。进一步的机理研究表明，该反应可能涉及由光诱导电子转移过程产生的超氧阴离子自由基。
• Carbamoyl substituted oxazoles as thromboxane receptor antagonists
  申请人：ELI LILLY AND COMPANY

  公开号：EP0811621A2

  公开（公告）日：1997-12-10

  This invention relates to carbamoyl substituted heterocycles which are ω-phenyl-ω-(3-pyridyl)-ω-alkenoic acid derivatives bearing a carbamoyl substituted oxazolyl or oxazolinyl group on the phenyl ring and which demonstrate utility for thromboxane receptor antagonism and/or thromboxane synthase inhibition, as well as pharmaceutical formulations containing them, methods for their use, and processes and intermediates for their preparation.

  本发明涉及氨基甲酰基取代的杂环，这些杂环是ω-苯基-ω-(3-吡啶基)-ω-烯酸衍生物，在苯基环上带有氨基甲酰基取代的噁唑基或噁唑啉基，具有血栓素受体拮抗和/或血栓素合成酶抑制作用，还涉及含有这些杂环的药物制剂、使用方法以及制备这些杂环的工艺和中间体。
• Preparation of substituted alkenoic acids
  申请人：ELI LILLY AND COMPANY

  公开号：EP0816361A2

  公开（公告）日：1998-01-07

  This invention relates to a highly selective process for preparation of E-ω-phenyl-ω-(3-pyridyl)-ω-alkenoic acid derivatives bearing a carbamoyl substituted oxazolyl or oxazolinyl group on the phenyl ring which demonstrate utility for thromboxane receptor antagonism and/or thromboxane synthase inhibition, as well as to intermediates therefor.

  本发明涉及一种制备 E-ω-苯基-ω-(3-吡啶基)-ω-烯酸衍生物的高选择性工艺，该衍生物在苯基环上带有氨基甲酰基取代的噁唑基或噁唑啉基，可用于血栓素受体拮抗和/或血栓素合成酶抑制，本发明还涉及其中间体。
• US5849766A
  申请人：——

  公开号：US5849766A

  公开（公告）日：1998-12-15