N-[3-((1R,6S)-6-benzyloxymethyl-1-formyl-cyclohex-3-enyl)-propyl]-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-acetamide | 954148-46-0

• 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-formyl-cyclohex-3-enyl)-propyl]-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-acetamide
• 英文别名: 2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-N-[3-[(1R,6S)-1-formyl-6-(phenylmethoxymethyl)cyclohex-3-en-1-yl]propyl]acetamide
• CAS: 954148-46-0
• 化学式: C₂₅H₃₅NO₅
• 分子量: 429.557
• InChiKey: SYPPRQHRMXMWGW-OTNCWRBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[3-((1R,6S)-6-benzyloxymethyl-1-formyl-cyclohex-3-enyl)-propyl]-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-acetamide 在 2,6-二甲基吡啶 、 manganese(IV) oxide 、 selenium(IV) oxide 、 tin(ll) chloride 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 41.0h， 生成 (1R,2'S,6S,9a'S)-6-(benzyloxymethyl)-2'-((triisopropylsilyloxy)methyl)-6',7',8',9a'-tetrahydro-2'H-spiro[cyclohex[3]ene-1,9'-pyrido[2,1-b][1,3]oxazin]-2,4'(3'H)-dione
  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：

  ((1R,6S)-6-(hydroxymethyl)cyclohex-3-en-1-yl)methyl acetate 在 2,6-二甲基吡啶 、 lithium hydroxide 、 jones' reagent 、 4 A molecular sieve 、 二苯基膦叠氮化物 、 四丁基氟化铵 、 水 、 magnesium oxide 、 二异丁基氢化铝 、 N-甲基吗啉氧化物 、 N,N-二异丙基乙胺 、 乙酰氯 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 30.75h， 生成 N-[3-((1R,6S)-6-benzyloxymethyl-1-formyl-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

文献信息

• Preparation of Novel Polycyclic Heterocycles Using a Tin(II) Chloride Dihydrate-Mediated Deacetalisation-Bicyclisation Sequence
  作者：Richard Taylor、Alex Cayley、Katherine Gallagher、Cécilia Ménard-Moyon、Jan Schmidt、Louis Diorazio

  DOI：10.1055/s-0028-1083214

  日期：2008.12

  Tin(II) chloride dihydrate-mediated deacetalisation- bicyclisation procedures for the construction of novel polycyclic heterocycles from amides possessing a pendant acetal group are re- ported. Optimisation and scoping studies are described; using this methodology, a range of known, and novel, ring-fused heterocyclic systems have been prepared, some in enantiomerically pure form.

  报道了二水合氯化锡（II）介导的脱缩醛化-双环化过程，用于从具有侧缩缩醛基团的酰胺构建新型多环杂环。描述了优化和范围研究；使用这种方法，已经制备了一系列已知的和新颖的稠环杂环系统，其中一些是对映体纯的形式。
• The First Synthesis of the ABC-Ring System of ‘Upenamide
  作者：Jan Peter Schmidt、Sandra Beltrán-Rodil、Rhona J. Cox、Graeme D. McAllister、Mark Reid、Richard J. K. Taylor

  DOI：10.1021/ol701772d

  日期：2007.9.1

  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.