10',11',11'-Trimethylspiro[1,3-dioxolane-2,6'-bicyclo[5.3.1]undec-1(10)-ene]-2'-one | 1025773-77-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 10',11',11'-Trimethylspiro[1,3-dioxolane-2,6'-bicyclo[5.3.1]undec-1(10)-ene]-2'-one
• CAS: 1025773-77-6
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: IGBGQODXADQDIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  10',11',11'-Trimethylspiro[1,3-dioxolane-2,6'-bicyclo[5.3.1]undec-1(10)-ene]-2'-one 在 lithium diisopropyl amide 、 MoO5*pyridine*HMPA 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 18.0h， 以94%的产率得到
  参考文献：
  名称：

  A novel route for the construction of Taxol ABC-ring framework: skeletal rearrangement approach to AB-ring and intramolecular aldol approach to C-ring

  摘要：

  We report here on the construction of the ABC-ring framework of (+/-)-Taxol using an intramolecular aldol reaction as a key step. AB-ring compound 8 was converted to ketoaldehyde 25 as a precursor of an aldol reaction via introduction of oxygen-functionalities and a methoxycarbony] group, which can be converted to a methyl group, in the proper positions of the B-ring. An aldol reaction of ketoaldehyde with LDA led to the formation of the desired product 27, which corresponds to the ABC-ring framework of (+/-)-Taxol. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.039
• 作为产物：
  描述：

  乙二醇 、 10,11,11-Trimethyl-bicyclo[5.3.1]undec-1(10)-ene-2,6-dione 在 D(+)-10-樟脑磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以97%的产率得到10',11',11'-Trimethylspiro[1,3-dioxolane-2,6'-bicyclo[5.3.1]undec-1(10)-ene]-2'-one
  参考文献：
  名称：

  A novel route for the construction of Taxol ABC-ring framework: skeletal rearrangement approach to AB-ring and intramolecular aldol approach to C-ring

  摘要：

  We report here on the construction of the ABC-ring framework of (+/-)-Taxol using an intramolecular aldol reaction as a key step. AB-ring compound 8 was converted to ketoaldehyde 25 as a precursor of an aldol reaction via introduction of oxygen-functionalities and a methoxycarbony] group, which can be converted to a methyl group, in the proper positions of the B-ring. An aldol reaction of ketoaldehyde with LDA led to the formation of the desired product 27, which corresponds to the ABC-ring framework of (+/-)-Taxol. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.039

文献信息

• A novel route for the construction of Taxol ABC-ring framework: skeletal rearrangement approach to AB-ring and intramolecular aldol approach to C-ring
  作者：Terumichi Enomoto、Tsumoru Morimoto、Mifuyu Ueno、Takanori Matsukubo、Yumi Shimada、Ken Tsutsumi、Ryuichi Shirai、Kiyomi Kakiuchi

  DOI：10.1016/j.tet.2008.02.039

  日期：2008.4

  We report here on the construction of the ABC-ring framework of (+/-)-Taxol using an intramolecular aldol reaction as a key step. AB-ring compound 8 was converted to ketoaldehyde 25 as a precursor of an aldol reaction via introduction of oxygen-functionalities and a methoxycarbony] group, which can be converted to a methyl group, in the proper positions of the B-ring. An aldol reaction of ketoaldehyde with LDA led to the formation of the desired product 27, which corresponds to the ABC-ring framework of (+/-)-Taxol. (c) 2008 Elsevier Ltd. All rights reserved.