(+)-(1S,4S,5RS,6aS)-1-tert-butoxy-4,6a-dimethyl-1,2,4,5,6,6a-hexahydro-4-(3-hydroxypropyl)-5-(methoxycarbonyl)pentalene | 135395-32-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+)-(1S,4S,5RS,6aS)-1-tert-butoxy-4,6a-dimethyl-1,2,4,5,6,6a-hexahydro-4-(3-hydroxypropyl)-5-(methoxycarbonyl)pentalene
• 英文别名: methyl (3S,6S,6aS)-3-(3-hydroxypropyl)-3,6a-dimethyl-6-[(2-methylpropan-2-yl)oxy]-1,2,5,6-tetrahydropentalene-2-carboxylate
• CAS: 135395-32-3；135395-33-4
• 化学式: C₁₉H₃₂O₄
• 分子量: 324.461
• InChiKey: BTODYCFBMKNEAA-KNMKIOOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (+)-(1S,4S,5RS,6aS)-1-tert-butoxy-4,6a-dimethyl-1,2,4,5,6,6a-hexahydro-4-(3-hydroxypropyl)-5-(methoxycarbonyl)pentalene 在 sodium hypochlorite 、 pyridine-SO3 complex 、 盐酸羟胺 、 sodium acetate 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (+)-(1S,3S,4S,8R,11S)-11-tert-butoxy-1,4-dimethyl-3-(methoxycarbonyl)tricyclo<6.3.0.0^4,8>undecano<7,9-c,d>isoxazole
  参考文献：
  名称：

  A novel approach to angular triquinanes via intramolecular 1,3-dipolar cycloaddition of nitrile oxide

  摘要：

  The framework of angular triquinane sesquiterpenes was stereoselectively constructed via the intramolecular 1,3-dipolar cycloaddition of nitrile oxide precursors. Optically active indandione 9 was converted into olefinic oximes 18A and 18B through two successive alkylations, followed by ring contraction. Oxidation of the mixture 18A and 18B with sodium hypochlorite gave rise to tetracyclic isoxazolines 21A and 21B, which were transformed into tricyclo[6.3.0.0(4,8)]undecanes 28 and 29.

  DOI：

  10.1021/jo00018a014
• 作为产物：
  描述：

  (+)-(1S,7aS)-1-t-Butoxy-4-(3-t-butyldimethylsiloxypropyl)-7,7a-dihydro-7a-methylindan-5(6H)-one 在 对甲苯磺酰叠氮 、 potassium tert-butylate 、 四丁基氟化铵 、 sodium methylate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 34.02h， 生成 (+)-(1S,4S,5RS,6aS)-1-tert-butoxy-4,6a-dimethyl-1,2,4,5,6,6a-hexahydro-4-(3-hydroxypropyl)-5-(methoxycarbonyl)pentalene
  参考文献：
  名称：

  A novel approach to angular triquinanes via intramolecular 1,3-dipolar cycloaddition of nitrile oxide

  摘要：

  The framework of angular triquinane sesquiterpenes was stereoselectively constructed via the intramolecular 1,3-dipolar cycloaddition of nitrile oxide precursors. Optically active indandione 9 was converted into olefinic oximes 18A and 18B through two successive alkylations, followed by ring contraction. Oxidation of the mixture 18A and 18B with sodium hypochlorite gave rise to tetracyclic isoxazolines 21A and 21B, which were transformed into tricyclo[6.3.0.0(4,8)]undecanes 28 and 29.

  DOI：

  10.1021/jo00018a014

文献信息

• IHARA, MASATAKA;TOKUNAGA, YUJI;TANIGUCHI, NOBUAKI;FUKUMOTO, KEIICHIRO;KAB+, J. ORG. CHEM., 56,(1991) N8, C. 5281-5285
  作者：IHARA, MASATAKA、TOKUNAGA, YUJI、TANIGUCHI, NOBUAKI、FUKUMOTO, KEIICHIRO、KAB+

  DOI：——

  日期：——