(1R,8R)-1,7,7-Trimethyl-12-oxa-tricyclo[6.3.1.02,6]dodeca-2(6),4,9-trien-11-one | 861816-80-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (1R,8R)-1,7,7-Trimethyl-12-oxa-tricyclo[6.3.1.02,6]dodeca-2(6),4,9-trien-11-one
• CAS: 861816-80-0
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: WPRGCDHMPMGARN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(甲氧甲基)-N-(三甲基硅甲基)苄胺 、 (1R,8R)-1,7,7-Trimethyl-12-oxa-tricyclo[6.3.1.02,6]dodeca-2(6),4,9-trien-11-one 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以78%的产率得到
  参考文献：
  名称：

  Studies on the synthetic utility of [6+3] cycloaddition of pentafulvenes with 3-oxidopyrylium betaines: efficient synthesis of fused ring cyclooctanoids

  摘要：

  A study on the synthetic utility of [6+3] cycloaddition of pentafulvenes with 3-oxidopyrylium betaines is described. 5-8 Fused oxa-bridged cyclooctanoids, the products of the above methodology undergo facile Diels-Alder reaction, dipolar cycloaddition, Luche reduction and selective hydrogenation over Pd/C leading to functionalized molecules, which can be transformed to oxa-bridged fused cyclooctanoids. We have shown that the carbon framework of the molecules can be directly expanded from the product, thus enhancing the synthetic versatility of the products. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.102
• 作为产物：
  描述：

  DL-1-(2-呋喃基)乙醇 在 吡啶 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 6.0h， 生成 (1R,8R)-1,7,7-Trimethyl-12-oxa-tricyclo[6.3.1.02,6]dodeca-2(6),4,9-trien-11-one
  参考文献：
  名称：

  [6+3] Cycloaddition of pentafulvenes with 3-oxidopyrylium betaine: a novel methodology toward the synthesis of 5–8 fused oxabridged cyclooctanoids

  摘要：

  Pentafulvenes undergo a facile [6+3] cycloaddition with 3-oxidopyrylium betaine, generated from the corresponding pyranulose acetate, leading to the formation of 5-8 fused oxabridged cyclooctanoids. The product is formed by a [6+3] cycloaddition, followed by a 1,5-hydrogen shift of the initially formed [6+3] adduct. The reaction was found to be general and a number of fulvenes with a wide range of substituents at the exocyclic double bond, that is, at the C6 position followed a similar reactivity pattern. The [6+3] adduct, a 5-8 fused oxabridged cyclooctanoid, is potentially amenable to a number of synthetic transformations due to the presence of an alpha, beta-unsaturated ketone and cyclopentadiene part. By selecting appropriately substituted fulvene and pyranulose acetates, it is possible to use this methodology for the synthesis of a wide range of 5-8 fused cyclooctanoids. The experimental results have been rationalized on the basis of theoretical calculations. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.017

文献信息

• [6+3] Cycloaddition of fulvenes with 3-oxidopyrylium betaine: a novel methodology for the synthesis of fused cyclooctanoid natural products
  作者：K.V. Radhakrishnan、K. Syam Krishnan、Mohan M. Bhadbhade、Gaurav V. Bhosekar

  DOI：10.1016/j.tetlet.2005.05.042

  日期：2005.7

  Fulvenes undergo an easy [6+3] cycloaddition with 3-oxidopyrylium betaines leading to 5–8 fused oxabridged cyclooctanoids.

  富勒烯与3个氧化吡啶鎓甜菜碱容易进行[6 + 3]环加成反应，从而生成5–8个稠合的氧桥联环庚烷类化合物。