(4aR,8aR)-4a-allyl-8a-methylhexahydro-1H-spiro[naphthalene-2,2'-[1,3]dioxolan]-5(3H)-one | 1224845-52-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aR,8aR)-4a-allyl-8a-methylhexahydro-1H-spiro[naphthalene-2,2'-[1,3]dioxolan]-5(3H)-one
• CAS: 1224845-52-6
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: RLGSESXTDVYFFU-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4aR,8aR)-4a-allyl-8a-methylhexahydro-1H-spiro[naphthalene-2,2'-[1,3]dioxolan]-5(3H)-one 、 甲基三苯基溴化膦 在 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 17.0h， 生成 (4aS,8aR)-4a-allyl-8a-methyl-5-methyleneoctahydro-1H-spiro[naphthalene-2,2'-[1,3]dioxolane]
  参考文献：
  名称：

  Total Synthesis of (−)-Anominine

  摘要：

  The first total synthesis of anominine has been achieved, and the absolute configuration of the product has been determined. The key features include the development of a new, highly efficient organocatalyzed method for the asymmetric synthesis of Wieland-Miescher ketone building blocks, an unusual selenoxide [2,3]-sigmatropic rearrangement, and a ZrCl(4)-catalyzed indole coupling as well as several chemoselective transformations controlled by the structurally congested nature of the bicyclic core.

  DOI：

  10.1021/ja101994q
• 作为产物：
  描述：

  2-乙基-2-甲基-1,3-二氧杂烷 、 (4aR,8aR)-8a-allyl-4a-methylhexahydronaphthalene-1,6-(2H,7H)-dione 在 对甲苯磺酸 作用下， 反应 1.0h， 生成 (4aR,8aR)-4a-allyl-8a-methylhexahydro-1H-spiro[naphthalene-2,2'-[1,3]dioxolan]-5(3H)-one
  参考文献：
  名称：

  Total Synthesis of (−)-Anominine

  摘要：

  The first total synthesis of anominine has been achieved, and the absolute configuration of the product has been determined. The key features include the development of a new, highly efficient organocatalyzed method for the asymmetric synthesis of Wieland-Miescher ketone building blocks, an unusual selenoxide [2,3]-sigmatropic rearrangement, and a ZrCl(4)-catalyzed indole coupling as well as several chemoselective transformations controlled by the structurally congested nature of the bicyclic core.

  DOI：

  10.1021/ja101994q