2,2-二甲基-6-羟基-1-(四氢吡喃氧基)己烷 | 615288-01-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2,2-二甲基-6-羟基-1-(四氢吡喃氧基)己烷
• 英文名称: 2,2-dimethyl-6-hydroxy-1(tetrahydropyranyloxy)hexane
• 英文别名: 5,5-dimethyl-6-(tetrahydropyran-2-yloxy)hexan-1-ol；5-5-dimethyl-6-(tetrahydropyran-2-yloxy)-hexan-1-ol；5,5-dimethyl-6-(tetrahydropyran-2-yloxy)-hexan-1-ol；5,5-Dimethyl-6-(oxan-2-yloxy)hexan-1-ol
• CAS: 615288-01-2
• 化学式: C₁₃H₂₆O₃
• 分子量: 230.348
• InChiKey: CLEFBHYYFHTNRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  7
• 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：

  2,2-二甲基-6-羟基-1-(四氢吡喃氧基)己烷 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 22.0h， 生成 6-(6-Hydroxy-5-methyl-5-phenylhexyloxy)-2,2-dimethyl-hexan-1-ol
  参考文献：
  名称：

  Long Hydrocarbon Chain Ether Diols and Ether Diacids That Favorably Alter Lipid Disorders in Vivo

  摘要：

  Long hydrocarbon chain ethers with bis-terminal hydroxyl or carboxyl groups have been synthesized and evaluated for their potential to favorably alter lipid disorders including metabolic syndrome. Compounds were assessed for their effects on the de novo incorporation of radiolabeled acetate into lipids in primary cultures of rat hepatocytes as well as for their effects on lipid and glycemic variables in female obese Zucker fatty rats following 1 and 2 weeks of daily oral administration. The most active compounds were found to be symmetrical with four to five methylene groups separating the central ether functionality and the gem dimethyl or methyl/aryl substituents. Biological activity was found to be greatest for tetramethyl-substituted ether diols (e.g., 28 and 31), while bis(arylmethyl) derivatives (e.g., 10, 11, and 27), diethers (e.g., 49, 50, and 56), and diphenyl ethers (e.g., 35 and 36) were the least active. For the most biologically active compound 28, we observed as much as a 346% increase in serum HDL-cholesterol and a 71% reduction in serum triglycerides at the highest dose administered (100 mg/kg) after 2 weeks of treatment. For compound 31 we observed a 69% reduction in non-HDL-cholesterol, accompanied by a 131% increase in HDL-cholesterol and an 84% reduction in serum triglycerides under the same treatment conditions.

  DOI：

  10.1021/jm0400395
• 作为产物：
  描述：

  6-溴-2,2-二甲基己酸乙酯 在 甲醇 、 锂硼氢 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 81.0h， 生成 2,2-二甲基-6-羟基-1-(四氢吡喃氧基)己烷
  参考文献：
  名称：

  公斤级合成双（6-羟基-5,5-二甲基己基）醚 (ESP24232)，一种新型降脂剂

  摘要：

  因此需要进一步的生物学研究和潜在的临床试验。类似于 1 的结构，例如二酸 2 3 3 4 和 3，s 是已知的，并且也已成功测试其降低胆固醇的作用。在这项工作中，描述了从实验室规模到千克规模的 1 合成的发展。特别强调避免使用有毒和有害的溶剂和试剂、合成序列的可重复性、最终产品中杂质的去除和鉴定以及进一步扩大规模的潜力。在初步尝试中，1（方案 I）',* 的合成从现在可商购的 6 4,4'-二氯丁基醚 (4) 开始：最初通过用磷酸处理 THF 制备

  DOI：

  10.1080/00304940409355976

文献信息

• Functionalized long chain derivatives as acyl coenzyme-A mimics, compositions thereof, and methods of cholesterol management and related uses
  申请人：——

  公开号：US20030236212A1

  公开（公告）日：2003-12-25

  The invention relates to novel Acyl coenzyme-A mimics, compositions comprising ketone compounds, and methods useful for treating and preventing cardiovascular diseases, dyslipidemias, dysproteinemias, and glucose metabolism disorders comprising administering a composition comprising a ketone compound. The Acyl coenzyme-A mimics, compositions, and methods of the invention are also useful for treating and preventing Alzheimer's Disease, Syndrome X, peroxisome proliferator activated receptor-related disorders, septicemia, thrombotic disorders, obesity, pancreatitis, hypertension, renal disease, cancer, inflammation, bacterial infection and impotence. In certain embodiments, the Acyl coenzyme-A mimics, compositions, and methods of the invention are useful in combination therapy with other therapeutics, such as hypocholesterolemic and hypoglycemic agents.

  该发明涉及新型酰辅酶A类似物，包含酮化合物的组合物，以及用于治疗和预防心血管疾病、血脂异常、蛋白异常和葡萄糖代谢紊乱的方法，包括给予含有酮化合物的组合物。该发明的酰辅酶A类似物、组合物和方法也适用于治疗和预防阿尔茨海默病、X综合征、过氧化物酶体增殖激活受体相关疾病、败血症、血栓性疾病、肥胖、胰腺炎、高血压、肾脏疾病、癌症、炎症、细菌感染和阳痿。在某些实施例中，该发明的酰辅酶A类似物、组合物和方法可与其他治疗药物（如降胆固醇和降血糖药物）联合治疗。
• Ether compounds and compositions for cholesterol management and related uses
  申请人：——

  公开号：US20040192771A1

  公开（公告）日：2004-09-30

  The present invention relates to novel ether compounds, compositions comprising ether compounds, and methods useful for treating and preventing cardiovascular diseases, dyslipidemias, dysproteinemias, and glucose metabolism disorders comprising administering a composition comprising an ether compound. The compounds, compositions, and methods of the invention are also useful for treating and preventing Alzheimer's Disease, Syndrome X, peroxisome proliferator activated receptor-related disorders, septicemia, thrombotic disorders, obesity, pancreatitis, hypertension, renal disease, cancer, inflammation, and impotence. In certain embodiments, the compounds, compositions, and methods of the invention are useful in combination therapy with other therapeutics, such as hypocholesterolemic and hypoglycemic agents.

  本发明涉及新型醚化合物、含有醚化合物的组合物，以及用于治疗和预防心血管疾病、血脂异常、蛋白异常和葡萄糖代谢紊乱的方法，包括给予含有醚化合物的组合物。该发明的化合物、组合物和方法还可用于治疗和预防阿尔茨海默病、综合征X、过氧化物酶体增殖子活化受体相关疾病、败血症、血栓性疾病、肥胖、胰腺炎、高血压、肾脏疾病、癌症、炎症和阳痿。在某些实施方式中，该发明的化合物、组合物和方法可与其他治疗药物（如降胆固醇和降血糖药物）联合治疗。
• [EN] ETHER COMPOUNDS AND COMPOSITIONS FOR CHOLESTEROL MANAGEMENT AND RELATED USES<br/>[FR] COMPOSES D'ETHER ET COMPOSITIONS POUR LE CONTROLE DE CHOLESTEROL ET UTILISATIONS ASSOCIEES
  申请人：ESPERION THERAPEUTICS INC

  公开号：WO2005068410A1

  公开（公告）日：2005-07-28

  The present invention relates to novel ether compounds, compositions comprising ether compounds, and methods useful for treating and preventing cardiovascular diseases, dyslipidemias, dysproteinemias, and glucose metabolism disorders comprising administering a composition comprising an ether compound. The compounds, compositions, and methods of the invention are also useful for treating and preventing Alzheimer's Disease, Syndrome X, peroxisome proliferator activated receptor-related disorders, septicemia, thrombotic disorders, obesity, pancreatitis, hypertension, renal disease, cancer, inflammation, and impotence. In certain embodiments, the compounds, compositions, and methods of the invention are useful in combination therapy with other therapeutics, such as hypocholesterolemic and hypoglycemic agents.

  本发明涉及新型醚化合物、包含醚化合物的组合物以及用于治疗和预防心血管疾病、血脂异常、蛋白异常和葡萄糖代谢紊乱的方法，包括给予含有醚化合物的组合物。该发明的化合物、组合物和方法还可用于治疗和预防阿尔茨海默病、X综合征、过氧化物酶体增殖激活受体相关疾病、败血症、血栓性疾病、肥胖、胰腺炎、高血压、肾脏疾病、癌症、炎症和阳痿。在某些实施方式中，该发明的化合物、组合物和方法可与其他治疗药物（如降胆固醇和降血糖药物）联合治疗时使用。
• Influence of Various Central Moieties on the Hypolipidemic Properties of Long Hydrocarbon Chain Diols and Diacids
  作者：Daniela C. Oniciu、Jean-Louis H. Dasseux、Jing Yang、Ralf Mueller、Emil Pop、Anna Denysenko、Caiming Duan、Tian-Bao Huang、Lianhao Zhang、Brian R. Krause、Sandra L. Drake、Narendra Lalwani、Clay T. Cramer、Brian Goetz、Michael E. Pape、Andrew McKee、Gregory J. Fici、Janell M. Lutostanski、Stephen C. Brown、Charles L. Bisgaier

  DOI：10.1021/jm050650j

  日期：2006.1.1

  A series of long (11-15) hydrocarbon chain diols and diacids with various central functional groups and terminal gem-dimethyl or -methyl/aryl substituents was synthesized and evaluated in both in vivo and in vitro assays for its potential to favorably alter lipid disorders including metabolic syndrome. Compounds were assessed for their effects on the de novo incorporation of radiolabeled acetate into lipids in primary cultures of rat hepatocytes, as well as for their effects on lipid and glycemic variables in obese female Zucker fatty rats, Crl:(ZUC)-faBR. The most active compounds were hydroxyl-substituted symmetrical diacids and diols with a 13-atom chain and terminal gem-dimethyl substituents. Furthermore, biological activity was enhanced by central substitution with O, C=O, S, S=O compared to the methylene analogues and was diminished for compounds with central functional groups such as carbamate, ester, urea, acetylmethylene, and hydroxymethylene.
• MIMICS OF ACYL COENZYME-A, COMPOSITIONS THEREOF, AND METHODS OF CHOLESTEROL MANAGEMENT AND RELATED USES
  申请人：Esperion Therapeutics Inc.

  公开号：EP1497247A2

  公开（公告）日：2005-01-19