[(1R,6S)-6-(phenylmethoxymethyl)cyclohex-3-en-1-yl]methyl acetate | 954148-52-8

• 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: [(1R,6S)-6-(phenylmethoxymethyl)cyclohex-3-en-1-yl]methyl acetate
• CAS: 954148-52-8
• 化学式: C₁₇H₂₂O₃
• 分子量: 274.36
• InChiKey: TVLKBKOIBPQEPP-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(1R,6S)-6-(phenylmethoxymethyl)cyclohex-3-en-1-yl]methyl acetate 在 2,6-二甲基吡啶 、 manganese(IV) oxide 、 lithium hydroxide 、 selenium(IV) oxide 、 jones' reagent 、 4 A molecular sieve 、 二苯基膦叠氮化物 、 四丁基氟化铵 、 水 、 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 、 tin(ll) chloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 50.75h， 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：

  cis-cyclohex-4-ene-1,2-diylbis(methylene) diacetate 在 sodium hydroxide 、 porcine pancreatic lipase 、 magnesium oxide 作用下， 以 phosphate buffer 为溶剂， 反应 45.0h， 生成 [(1R,6S)-6-(phenylmethoxymethyl)cyclohex-3-en-1-yl]methyl acetate
  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