(1S,5S,7S)-7-exo-hydroxymethyl-6,8-dioxa-3-azabicyclo[3.2.1]octane | 250137-96-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧氮杂卓类
• 英文名称: (1S,5S,7S)-7-exo-hydroxymethyl-6,8-dioxa-3-azabicyclo[3.2.1]octane
• 英文别名: (1S,5S,7S)-6,8-dioxa-3-azabicyclo[3.2.1]oct-7-ylmethanol；(6,8-dioxa-3-aza-bicyclo[3.2.1]oct-7-yl)-methanol；[(1S,5S,7S)-6,8-dioxa-3-azabicyclo[3.2.1]octan-7-yl]methanol
• CAS: 250137-96-3
• 化学式: C₆H₁₁NO₃
• 分子量: 145.158
• InChiKey: LQPGODDOSFMBMQ-ZLUOBGJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,5S,7S)-7-exo-hydroxymethyl-6,8-dioxa-3-azabicyclo[3.2.1]octane 在 四(三苯基膦)钯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  使用BTAa作为手性助剂的立体选择性Meisenheimer重排

  摘要：

  迈森海默重排涉及将烯丙基叔胺-N-氧化物[2,3]σ重排为O-烯丙基羟胺。各种BTAa（衍生自酒石酸和α-氨基酸的自行车）被用作手性助剂，用于通过BTAa's与肉桂基溴化物和（E）-2-甲基-n偶联而获得的N-烯丙胺的N-氧化物的Meisenheimer重排。乙酸2-戊烯酯。尽管N-氧化物的形成具有非对映选择性，但重排中的不对称诱导通常较低。然而，4-内在之间的相互作用BTAa上的基团和烯丙基部分上的2'-取代基可在[2,3]-σ过程中实现更有效的手性转移，在最佳情况下，de值高达65％。通过使用具有良好的醇和手性助剂回收率的Mo（CO）6，可以在重排产物中裂解N = O键。

  DOI：

  10.1016/s0957-4166(00)00402-x
• 作为产物：
  描述：

  methyl (1R,5S,7R)-3-benzyl-2-oxo-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-exo-carboxylate 在 palladium dihydroxide lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 14.0h， 生成 (1S,5S,7S)-7-exo-hydroxymethyl-6,8-dioxa-3-azabicyclo[3.2.1]octane
  参考文献：
  名称：

  Synthesis and Reactivity of Bicycles Derived from Tartaric Acid and α-Amino Acids:  A Novel Class of Conformationally Constrained Dipeptide Isosteres Based upon Enantiopure 3-Aza-6,8-dioxabicyclo[3.2.1]octane-7-carboxylic Acid

  摘要：

  3-Aza-6,8-dioxabicyclo[3.2.1]octane-7-carboxylic acids (named BTAa) derived from (R,R), (S,S)-, or meso-tartaric acid and natural (L), unnatural (D), or unusual alpha-amino acids are described as conformationally constrained dipeptide isosteres. The general strategy developed for their preparation has required the transformation of the amino acids into the corresponding N-benzylamino alcohols, followed by the PyBroP-promoted condensation with the monomethyl ester of the suitable 2,3-di-O-isopropylidenetartaric acid. Oxidation of the hydroxy group to aldheyde and subsequent acid-catalyzed trans-acetalization with the two hydroxy groups of the tartaric acid moiety provided 3-aza-2-oxo-6,8-dioxabicyclo [3.2.1] octane-7-carboxylic acid methyl esters [named BTAa(O)] in good yield and, in most cases, as single enantiopure diastereoisomers. This strategy has been applied to the preparation of BTAa(O) starting from (R,R)-, (S,S)-, or meso-tartaric acid and glycine, L- and D-phenylalanine, L- and D-alanine, and (+/-)-phenylglycine. In the cases of glycine, L- and D-phenylalanine, and L- and D-alanine, the selective reduction by BH3. DMS of the amide group succeeding to the cyclization step, or the reduction of both amide and ester functions followed by reoxidation of the hydroxy to carboxylic group, provided in good yield the 3-aza-3-benzyl-6,8-dioxabicyclo[3.2.1]-octane-7-carboxylic acids (or their methyl ester) BTAa, having the side chain of the amino acid precursors at position 4. The stability and rigidity of the bicyclic skeleton, the complete control of all the stereocenters, the possibility of introducing the side chains of L- or D-amino acids, and the demonstrated compatibility with the conditions required for solid-phase peptide synthesis make the BTAa compounds potential dipeptide isosteres useful for the synthesis of modified peptides.

  DOI：

  10.1021/jo9904967

文献信息

• Thiazole Derivatives and Use Thereof
  申请人：Quattropani Anna

  公开号：US20080188531A1

  公开（公告）日：2008-08-07

  The present invention is related to thiazole derivatives of Formula (I) in particular for the treatment and/or prophylaxis of autoimmune disorders and/or inflammatory diseases, cardiovascular diseases, neurodegenerative diseases, bacterial or viral infections, kidney diseases, platelet aggregation, cancer, transplantation, graft rejection or lung injuries.

  本发明涉及式（I）的噻唑衍生物，特别是用于治疗和/或预防自身免疫性疾病和/或炎症性疾病、心血管疾病、神经退行性疾病、细菌或病毒感染、肾脏疾病、血小板聚集、癌症、移植、移植排斥或肺损伤。
• Thiazole derivatives and use thereof
  申请人：Merck Serono S.A.

  公开号：US07799814B2

  公开（公告）日：2010-09-21

  The present invention is related to thiazole derivatives of Formula (I) in particular for the treatment and/or prophylaxis of autoimmune disorders and/or inflammatory diseases, cardiovascular diseases, neurodegenerative diseases, bacterial or viral infections, kidney diseases, platelet aggregation, cancer, transplantation, graft rejection or lung injuries.

  本发明涉及公式（I）的噻唑衍生物，特别是用于治疗和/或预防自身免疫性疾病和/或炎症性疾病、心血管疾病、神经退行性疾病、细菌或病毒感染、肾脏疾病、血小板聚集、癌症、移植、移植排斥或肺损伤。
• WO2006/125805
  申请人：——

  公开号：——

  公开（公告）日：——
• WO2006/125803
  申请人：——

  公开号：——

  公开（公告）日：——
• THIAZOLE DERIVATIVES AND USE THEREOF
  申请人：Merck Serono SA

  公开号：EP1888546B1

  公开（公告）日：2015-07-08