Spiro[1,3-dioxolane-2,1'(2'H)-naphthalene], 3',4',4'a,7',8',8'a-hexahydro-5',8'a-dimethyl-6'-[(trimethylsilyl)oxy]-, (4'aS,8'aS)- | 91547-53-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Spiro[1,3-dioxolane-2,1'(2'H)-naphthalene], 3',4',4'a,7',8',8'a-hexahydro-5',8'a-dimethyl-6'-[(trimethylsilyl)oxy]-, (4'aS,8'aS)-
• CAS: 91547-53-4
• 化学式: C₁₇H₃₀O₃Si
• 分子量: 310.509
• InChiKey: HYRQRXXABZWIFE-HOCLYGCPSA-N

物化性质

• 沸点：
  351.7±42.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Spiro[1,3-dioxolane-2,1'(2'H)-naphthalene], 3',4',4'a,7',8',8'a-hexahydro-5',8'a-dimethyl-6'-[(trimethylsilyl)oxy]-, (4'aS,8'aS)- 在 2,6-二甲基吡啶 、 盐酸 、 lithium chloride 、 lithium hexamethyldisilazane 、 tetramethylammonium triacetoxyborohydride 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 溶剂黄146 、 甲苯 、 乙腈 为溶剂， -78.0~140.0 ℃ 、4.67 kPa 条件下， 反应 20.33h， 生成 (S)-tert-butyl 2-((E)-((4aR,5R,6S,8aS)-6-(tert-butyldimethylsilyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-5,8a-dimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methyleneamino)-3,3-dimethylbutanoate
  参考文献：
  名称：

  Development of a Scalable Synthesis of a Common Eastern Tricyclic Lactone for Construction of the Nodulisporic Acids

  摘要：

  A scalable, second-generation synthesis of the densely functionalized eastern tricyclic lactone (+)-6, a common intermediate, for construction of the nodulisporic acids has been achieved. Modifications to the first-generation route now permit access to (+)-6 in 17 steps with an overall 16.5% yield. Key carbon-carbon bond constructions include a Kirk-Petrow (phenylthio)methylation, a Sc(OTf)(3)-catalyzed hydroxymethylation, a Stille carbonylation, and a Koga three-component, conjugate addition-alkylation sequence.

  DOI：

  10.1021/op060204l
• 作为产物：
  描述：

  (S)-(+)-3,4,8,8a-四氢-8a-甲基-1,6-(2H,7H)-萘醌 在 氨 、 lithium 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 水 、 叔丁醇 为溶剂， 反应 97.38h， 生成 Spiro[1,3-dioxolane-2,1'(2'H)-naphthalene], 3',4',4'a,7',8',8'a-hexahydro-5',8'a-dimethyl-6'-[(trimethylsilyl)oxy]-, (4'aS,8'aS)-
  参考文献：
  名称：

  Development of a Scalable Synthesis of a Common Eastern Tricyclic Lactone for Construction of the Nodulisporic Acids

  摘要：

  A scalable, second-generation synthesis of the densely functionalized eastern tricyclic lactone (+)-6, a common intermediate, for construction of the nodulisporic acids has been achieved. Modifications to the first-generation route now permit access to (+)-6 in 17 steps with an overall 16.5% yield. Key carbon-carbon bond constructions include a Kirk-Petrow (phenylthio)methylation, a Sc(OTf)(3)-catalyzed hydroxymethylation, a Stille carbonylation, and a Koga three-component, conjugate addition-alkylation sequence.

  DOI：

  10.1021/op060204l

文献信息

• An efficient approach to chiral, nonracemic trans-decahydro-5,8a-dimethyl-1,6-naphthalenedione derivatives. Total synthesis of (+)-pallescensin A
  作者：Amos B. Smith、Richard Mewshaw

  DOI：10.1021/jo00194a003

  日期：1984.10