2-Methyl-5-brompentyl-tetrahydropyranylether | 33454-43-2

• 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-Methyl-5-brompentyl-tetrahydropyranylether
• 英文别名: 2-[(5-Bromo-2-methylpentyl)oxy]tetrahydro-2H-pyran；2-(5-bromo-2-methylpentoxy)oxane
• CAS: 33454-43-2
• 化学式: C₁₁H₂₁BrO₂
• 分子量: 265.191
• InChiKey: SRZQWQHQHRMZBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-bromo-2-methylpentanoic acid 在 硼烷四氢呋喃络合物 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 2-Methyl-5-brompentyl-tetrahydropyranylether
  参考文献：
  名称：

  Ring-closing metathesis and palladium-catalyzed formate reduction to 3-methyleneoxepanes. Formal synthesis of (−)-zoapatanol

  摘要：

  A sequence of ring-closing metathesis and palladium-catalyzed formate reduction was developed for preparing O-heterocycles with an exocyclic olefin and applied to the asymmetric synthesis of zoapatanol. The key vicinal stereocenters in zoapatanol were constructed from the L-malic acid-derived lactone by successive chelation-controlled addition of alkyl groups. The O-allylations to prepare the dienes for RCM were achieved with the tertiary alcohols bearing internal olefins. The ring opening of oxepane, a new reaction pathway for the Pd-formate reduction, is also reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.023

文献信息

• [EN] NOVEL VITAMIN D ANALOGUES
  申请人：LEO PHARMACEUTICAL PRODUCTS LTD. A/S (LØVENS KEMISKE FABRIK PRODUKTIONSAKTIESELSKAB)

  公开号：WO1990009991A1

  公开（公告）日：1990-09-07

  (EN) The present invention relates to compounds of formula (I), in which formula R stands for an alkyl group containing from 7 to 12 carbon atoms optionally substituted with a hydroxy group; and derivatives of the compounds of formula (I) in which one or more hydroxy groups have been transformed into -O-acyl or -O-glycosyl or phosphate ester groups, such masked groups being hydrolyzable $i(in vivo), in pure form or in mixtures. The present compounds find use in both the human and veterinary practice in the treatment and prophylaxis of autoimmune diseases, including diabetes mellitus, hypertension, inflammatory diseases such as rheumatoid arthritis and asthma as well as diseases characterized by abnormal cell differentiation and/or cell proliferation, and/or imbalance in the immune system.(FR) La présente invention se rapporte à des composés représentés par la formule (I), où R représente un groupe alkyle contenant 7 à 12 atomes de carbone, éventuellement substitués par un groupe hydroxy; ainsi qu'à des dérivés des composés de la formule (I), dans lesquels un ou plusieurs groupes hydroxy ont été transformés en groupe -O-acyle ou -O-glycosyle ou en groupes d'ester de phosphate, ces groupes masqués étant hydrolysables $i(in vivo) sous forme pure ou mélangés. Lesdits composés sont utilisables en médecine humaine et vétérinaire pour le traitement et la prophylaxie de maladies auto-immunitaires, y compris le diabète sucré, l'hypertension, les maladies inflammatoires, telles que l'arthrite rhumatoïde et l'asthme, ainsi que les maladies se caractérisant par une différenciation cellulaire et/ou une prolifération cellulaire anormales et/ou un déséquilibre du système immunitaire.

  本发明涉及化学式（I）的化合物，其中R表示含有7至12个碳原子的烷基，可选地被羟基取代；以及化学式（I）的化合物的衍生物，在其中一个或多个羟基被转化为-O-酰基或-O-糖基或磷酸酯基，这些掩蔽基在纯形式或混合物中是可水解的。这些化合物在人类和兽医学实践中用于治疗和预防自身免疫性疾病，包括糖尿病、高血压、炎症性疾病如类风湿性关节炎和哮喘，以及细胞分化和/或细胞增殖异常和/或免疫系统失衡的疾病。
• NOVEL VITAMIN D ANALOGUES
  申请人：LEO PHARMACEUTICAL PRODUCTS LTD. A/S (LOVENS KEMISKE FABRIK PRODUKTIONSAKTIESELSKAB)

  公开号：EP0460032A1

  公开（公告）日：1991-12-11
• US5401732A
  申请人：——

  公开号：US5401732A

  公开（公告）日：1995-03-28
• Ring-closing metathesis and palladium-catalyzed formate reduction to 3-methyleneoxepanes. Formal synthesis of (−)-zoapatanol
  作者：Hsiu-Yi Cheng、Yu-Shiang Lin、Chong-Si Sun、Ting-Wen Shih、Hui-Hsu Gavin Tsai、Duen-Ren Hou

  DOI：10.1016/j.tet.2011.10.023

  日期：2012.1

  A sequence of ring-closing metathesis and palladium-catalyzed formate reduction was developed for preparing O-heterocycles with an exocyclic olefin and applied to the asymmetric synthesis of zoapatanol. The key vicinal stereocenters in zoapatanol were constructed from the L-malic acid-derived lactone by successive chelation-controlled addition of alkyl groups. The O-allylations to prepare the dienes for RCM were achieved with the tertiary alcohols bearing internal olefins. The ring opening of oxepane, a new reaction pathway for the Pd-formate reduction, is also reported. (C) 2011 Elsevier Ltd. All rights reserved.