N-[3-((1R,6S)-6-benzyloxymethyl-1-hydroxymethyl-cyclohex-3-enyl)-propyl]-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-acetamide | 954148-45-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[3-((1R,6S)-6-benzyloxymethyl-1-hydroxymethyl-cyclohex-3-enyl)-propyl]-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-acetamide
• CAS: 954148-45-9
• 化学式: C₂₅H₃₇NO₅
• 分子量: 431.572
• InChiKey: GXGUPGXDTRLAPJ-OTNCWRBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  31.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  77.02
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-[3-((1R,6S)-6-benzyloxymethyl-1-hydroxymethyl-cyclohex-3-enyl)-propyl]-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-acetamide 在 吡啶 、 4 A molecular sieve 、 N-甲基吗啉氧化物 、 tin(ll) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 77.5h， 生成 ((1R,2'S,6S,9a'S)-6-(benzyloxymethyl)-4'-oxo-3',4',6',7',8',9a'-hexahydro-2'H-spiro[cyclohex[3]ene-1,9'-pyrido[2,1-b][1,3]oxazin]-2'-yl)methyl anthracene-9-carboxylate
  参考文献：
  名称：

  The First Synthesis of the ABC-Ring System of ‘Upenamide

  摘要：

  The first synthetic route to the spirooxaquinolizidinone core (ABC core) of the macrocyclic marine alkaloid 'upenamide (1) has been developed. All five stereocenters were introduced with complete stereocontrol. The hydroxyl group at C-11 was introduced by a regio- and stereoselective SeO2-mediated allylic oxidation. The spirocyclic skeleton was formed by a stannous chloride induced deacetalization-bicyclization procedure. Further stereocenters were introduced by an enzymatic desymmetrization and by incorporation of an (S)-malic acid derived building block.

  DOI：

  10.1021/ol701772d
• 作为产物：
  描述：

  3-((1R,6S)-6-benzyloxymethyl-1-(triisopropylsilanyloxy)methyl-cyclohex-3-enyl)-propan-1-ol 在 二苯基膦叠氮化物 、 四丁基氟化铵 、 水 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 N-[3-((1R,6S)-6-benzyloxymethyl-1-hydroxymethyl-cyclohex-3-enyl)-propyl]-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-acetamide
  参考文献：
  名称：

  The First Synthesis of the ABC-Ring System of ‘Upenamide

  摘要：

  The first synthetic route to the spirooxaquinolizidinone core (ABC core) of the macrocyclic marine alkaloid 'upenamide (1) has been developed. All five stereocenters were introduced with complete stereocontrol. The hydroxyl group at C-11 was introduced by a regio- and stereoselective SeO2-mediated allylic oxidation. The spirocyclic skeleton was formed by a stannous chloride induced deacetalization-bicyclization procedure. Further stereocenters were introduced by an enzymatic desymmetrization and by incorporation of an (S)-malic acid derived building block.

  DOI：

  10.1021/ol701772d