(1S,2R,4S,8R,10R,11R,12S,14R)-5-ethoxy-8-(methoxymethyl)-4,14-dimethyl-11-triethylsilyloxy-15-oxatetracyclo[10.2.1.01,10.02,6]pentadec-5-en-4-ol | 366492-09-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (1S,2R,4S,8R,10R,11R,12S,14R)-5-ethoxy-8-(methoxymethyl)-4,14-dimethyl-11-triethylsilyloxy-15-oxatetracyclo[10.2.1.01,10.02,6]pentadec-5-en-4-ol
• CAS: 366492-09-3
• 化学式: C₂₆H₄₆O₅Si
• 分子量: 466.734
• InChiKey: PVFLCAHQFSMXGB-IXICPSIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2R,4S,8R,10R,11R,12S,14R)-5-ethoxy-8-(methoxymethyl)-4,14-dimethyl-11-triethylsilyloxy-15-oxatetracyclo[10.2.1.01,10.02,6]pentadec-5-en-4-ol 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 作用下， 以 苯 为溶剂， 以84%的产率得到(1R,2S,4S,5S,7R,9R,11R,12R,13S,15R)-5-ethoxy-9-(methoxymethyl)-4,15-dimethyl-12-triethylsilyloxy-6,16-dioxapentacyclo[11.2.1.01,11.02,7.05,7]hexadecan-4-ol
  参考文献：
  名称：

  Rearrangement of a Tricyclic 2,5-Cyclohexadienone: Towards a General Synthetic Route to the Daphnanes and (+)-Resiniferatoxin

  摘要：

  Light as a reagent: A highly functionalized structure that serves as a daphnane template can be formed by the photorearrangement of a 2,5-cyclohexadienone subunit within a complex tricyclic ring system. The chemistry we describe should not only find use in the total synthesis of resiniferatoxin and related daphnanes, but should also provide useful templates for access to complex analogues.

  DOI：

  10.1002/1521-3773(20010716)40:14<2694::aid-anie2694>3.0.co;2-d
• 作为产物：
  描述：

  (S)-tert-butyldimethyl(pent-4-yn-2-yloxy)silane 在 palladium on activated charcoal 、 dicobalt octacarbonyl 咪唑 、 四氧化锇 、 正丁基锂 、 N-甲基吲哚酮 、 cerium(III) chloride 、 2-甲基-2-丁醇 、 四丁基氟化铵 、 氢气 、 potassium 2-methylbutan-2-olate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 、 丙酮 、 正戊烷 为溶剂， 生成 (1S,2R,4S,8R,10R,11R,12S,14R)-5-ethoxy-8-(methoxymethyl)-4,14-dimethyl-11-triethylsilyloxy-15-oxatetracyclo[10.2.1.01,10.02,6]pentadec-5-en-4-ol
  参考文献：
  名称：

  Rearrangement of a Tricyclic 2,5-Cyclohexadienone: Towards a General Synthetic Route to the Daphnanes and (+)-Resiniferatoxin

  摘要：

  Light as a reagent: A highly functionalized structure that serves as a daphnane template can be formed by the photorearrangement of a 2,5-cyclohexadienone subunit within a complex tricyclic ring system. The chemistry we describe should not only find use in the total synthesis of resiniferatoxin and related daphnanes, but should also provide useful templates for access to complex analogues.

  DOI：

  10.1002/1521-3773(20010716)40:14<2694::aid-anie2694>3.0.co;2-d

文献信息

• Rearrangement of a Tricyclic 2,5-Cyclohexadienone: Towards a General Synthetic Route to the Daphnanes and (+)-Resiniferatoxin
  作者：Stona R. Jackson、Michael G. Johnson、Masafumi Mikami、Sojiro Shiokawa、Erick M. Carreira

  DOI：10.1002/1521-3773(20010716)40:14<2694::aid-anie2694>3.0.co;2-d

  日期：2001.7.16

  Light as a reagent: A highly functionalized structure that serves as a daphnane template can be formed by the photorearrangement of a 2,5-cyclohexadienone subunit within a complex tricyclic ring system. The chemistry we describe should not only find use in the total synthesis of resiniferatoxin and related daphnanes, but should also provide useful templates for access to complex analogues.