(S)-3-Bromo-2-methyl-1-<(tetrahydropyranyl)oxy>propane | 142633-16-7

• 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: (S)-3-Bromo-2-methyl-1-<(tetrahydropyranyl)oxy>propane
• 英文别名: (S)-2-(3-bromo-2-methylpropoxy)tetrahydro-2H-pyran；(S)-2-(3-bromo-2-methylpropoxy)tetrahydropyran；(2S)-3-Bromo-2-methyl-1-((tetrahydropyran-2-yl)oxy)propane；2-((S)-3-bromo-2-methylpropoxy)tetrahydropyrane；(S)-3-Bromo-2-methyl-1-[(tetrahydropyranyl)oxy]propane；2-[(2S)-3-bromo-2-methylpropoxy]oxane
• CAS: 142633-16-7
• 化学式: C₉H₁₇BrO₂
• 分子量: 237.137
• InChiKey: WFIZIPKQGKOEIP-VEDVMXKPSA-N

物化性质

• 沸点：
  260.4±30.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 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：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-3-Bromo-2-methyl-1-<(tetrahydropyranyl)oxy>propane 在 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 、 二甲基亚砜 为溶剂， 反应 6.0h， 生成 (2'RS,3R)-3-methyl-4-(2-tetrahydropyranyloxy)butanal
  参考文献：
  名称：

  On the mechanism of Lewis acid promoted ene cyclizations of .omega.-unsaturated aldehydes

  摘要：

  The diastereomerically labeled d1 enals 1 and 2 were prepared from (S)-3-bromo-2-methylpropanol 5 by a sequence involving homologation to the allylic alcohol 13 and Sharpless epoxidation to either the alpha- or the beta-epoxide diastereomers 14 or 15. Reduction with LiAlD4 afforded the diastereomerically deuterated diols 16 and 20, respectively. Deoxygenation of the thionocarbonate derivatives 17 and 21 followed by THP ether cleavage and Swern oxidation afforded aldehydes 1 and 2. The undeuterated aldehyde 28 was similarly prepared. Cyclization of 1 and 2 with Me2AlCl afforded the cis-(E)-ethylidenecyclohexanols 3 and 4, respectively, as the major products in accord with a mechanism involving internal proton or deuteron transfer from the vinylic CHD grouping to the aldehyde carbonyl. Product ratios (E:Z, cis:trans) from the two aldehydes were significantly different, indicative of a substantial isotope effect.

  DOI：

  10.1021/jo00048a016
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 (S)-(+)-3-溴-2-甲基-1-丙醇 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到(S)-3-Bromo-2-methyl-1-<(tetrahydropyranyl)oxy>propane
  参考文献：
  名称：

  SPIRO(5.5)UNDECANE DERIVATIVES

  摘要：

  这项发明涉及具有与μ-阿片受体和ORL 1-受体亲和性的化合物，其生产方法，含有这些化合物的药物以及利用这些化合物治疗疼痛和其他疾病的用途。

  公开号：

  US20090247505A1

文献信息

• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：GLAXO GROUP LTD

  公开号：WO2012067663A1

  公开（公告）日：2012-05-24

  The present invention features compounds of formula (I): and salts thereof, pharmaceutical compositions comprising said compounds, and uses of such compounds in treating or preventing viral infections, such as HCV infections, and diseases associated with such infections.

  本发明涉及式(I)的化合物及其盐，包括所述化合物的药物组合物，以及利用这些化合物治疗或预防病毒感染，如HCV感染，以及与此类感染相关的疾病。
• Control of Diastereoselectivity by Solvent Effects in the Addition of Grignard Reagents to Enantiopure <i>t</i>-Butylsulfinimine:  Syntheses of the Stereoisomers of the Hydroxyl Derivatives of Sibutramine
  作者：Bruce Z. Lu、Chris Senanayake、Nansheng Li、Zhengxu Han、Roger P. Bakale、Stephen A. Wald

  DOI：10.1021/ol0507017

  日期：2005.6.1

  [reaction: see text] An efficient method has been developed to prepare all four isomers of the hydroxyl derivatives of sibutramine by addition of Grignard reagents (R)- or (S)-5 to a single enantiomer of sulfinyl imine (R)-1 simply by tuning the reaction solvent. The phenomenon of the reversed diastereoselectivity in CH(2)Cl(2) and THF implied that the reaction may proceed through a chelated cyclic

  [反应：见正文]已开发出一种有效的方法，可通过将Grignard试剂（R）-或（S）-5加到亚磺酰基亚胺（R）-1的单个对映体中来制备西布曲明的羟基衍生物的所有四个异构体只需通过调节反应溶剂即可。CH（2）Cl（2）和THF中非对映选择性的逆转现象暗示该反应可能通过CH（2）Cl（2）中的螯合的环状过渡态和THF中的非螯合的无环过渡态进行。
• Spiro(5.5)undecane derivatives
  申请人：Grunenthal GmbH

  公开号：US08288430B2

  公开（公告）日：2012-10-16

  The invention relates to compounds that have an affinity to the μ-opioid receptor and the ORL 1-receptor, methods for their production, medications containing these compounds and the use of these compounds for the treatment of pain and other conditions.

  本发明涉及具有对μ-阿片受体和ORL 1-受体亲和力的化合物，其制备方法，含有这些化合物的药物以及利用这些化合物治疗疼痛和其他疾病的用途。
• The First Potent Inhibitors for Human Glutaminyl Cyclase:  Synthesis and Structure−Activity Relationship
  作者：Mirko Buchholz、Ulrich Heiser、Stephan Schilling、André J. Niestroj、Katrin Zunkel、Hans-Ulrich Demuth

  DOI：10.1021/jm050756e

  日期：2006.1.1

  The first effective inhibitors for human glutaminyl cyclase (QC) are described. The structures are developed by applying a ligand-based optimization approach starting from imidazole. Screening of derivatives of that heterocycle led to compounds of the imidazol-1-yl-alkyl thiourea type as a lead scaffold. A library of thiourea derivatives was synthesized, resulting in an inhibitory improvement by 2 orders of magnitude, leading to 1-(3-(1H-imidazol-1-yl)propyl)-3-(3,4-dimethoxyphenyl)thiourea as a potent inhibitor. Systematic exploitation of the scaffold revealed a strong impact on the inhibitory efficacy and resulted in the development of imidazole-propyl-thioamides as another new class of potent inhibitors. A flexible alignment of the most potent compounds of the thioamide and thiourea class and a QC substrate revealed a good match of characteristic features of the molecules, which suggests a similar binding mode of both inhibitors and the substrate to the active site of QC.
• US6071932
  申请人：——

  公开号：——

  公开（公告）日：——