[3,3-Dimethyl-2-(3-methylbut-3-enyl)-5-(2-methylpropoxy)cyclohexa-1,5-dien-1-yl] prop-2-enyl carbonate | 1237493-45-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: [3,3-Dimethyl-2-(3-methylbut-3-enyl)-5-(2-methylpropoxy)cyclohexa-1,5-dien-1-yl] prop-2-enyl carbonate
• CAS: 1237493-45-6
• 化学式: C₂₁H₃₂O₄
• 分子量: 348.483
• InChiKey: WMHHATCVBUNQPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [3,3-Dimethyl-2-(3-methylbut-3-enyl)-5-(2-methylpropoxy)cyclohexa-1,5-dien-1-yl] prop-2-enyl carbonate 在 Pd(dmdba)₂ 、 (S)-4-叔丁基-2-[2-(二苯基膦基)苯基]-2-噁唑啉 作用下， 以 苯 为溶剂， 反应 1.13h， 生成 5,5-dimethyl-6-(3-methylbut-3-enyl)-3-(2-methylpropoxy)-6-prop-2-enylcyclohex-2-en-1-one
  参考文献：
  名称：

  A general enantioselective route to the chamigrene natural product family

  摘要：

  Described in this report is an enantioselective route toward the chamigrene natural product family. The key disconnections in our synthetic approach include sequential enantioselective decarboxylative allylation and ring-closing olefin metathesis to form the all-carbon quaternary stereocenter and spirocyclic core present in all members of this class of compounds. The generality of this strategy is demonstrated by the first total syntheses of elatol and the proposed structure of laurencenone B, as well as the first enantioselective total syntheses of laurencenone C and alpha-chamigrene. A brief exploration of the substrate scope of the enantioselective decarboxylative allylation/ring-closing metathesis sequence with fully substituted vinyl chlorides is also presented. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.128
• 作为产物：
  描述：

  5,5-Dimethyl-6-(3-methylbut-3-enyl)-3-(2-methylpropoxy)cyclohex-2-en-1-one 、 氯甲酸烯丙酯 在 正丁基锂 、 二异丙胺 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.81h， 生成 [3,3-Dimethyl-2-(3-methylbut-3-enyl)-5-(2-methylpropoxy)cyclohexa-1,5-dien-1-yl] prop-2-enyl carbonate
  参考文献：
  名称：

  A general enantioselective route to the chamigrene natural product family

  摘要：

  Described in this report is an enantioselective route toward the chamigrene natural product family. The key disconnections in our synthetic approach include sequential enantioselective decarboxylative allylation and ring-closing olefin metathesis to form the all-carbon quaternary stereocenter and spirocyclic core present in all members of this class of compounds. The generality of this strategy is demonstrated by the first total syntheses of elatol and the proposed structure of laurencenone B, as well as the first enantioselective total syntheses of laurencenone C and alpha-chamigrene. A brief exploration of the substrate scope of the enantioselective decarboxylative allylation/ring-closing metathesis sequence with fully substituted vinyl chlorides is also presented. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.128

文献信息

• The Catalytic Asymmetric Total Synthesis of Elatol
  作者：David E. White、Ian C. Stewart、Robert H. Grubbs、Brian M. Stoltz

  DOI：10.1021/ja710294k

  日期：2008.1.1

  Described in this report is the first total synthesis of elatol, a halogenated sesquiterpene in the chamigrene natural product family. The key disconnections in our synthetic approach include an enantioselective decarboxylative allylation to form the all-carbon quaternary stereocenter and a ring-closing olefin metathesis to concomitantly form the spirocyclic core as well as the fully substituted chlorinated olefin. This strategy represents a general platform for accessing the chamigrene natural product family, as demonstrated by the synthesis of (+)-laurencenone B as an intermediate in our route.
• A general enantioselective route to the chamigrene natural product family
  作者：David E. White、Ian C. Stewart、Brinton A. Seashore-Ludlow、Robert H. Grubbs、Brian M. Stoltz

  DOI：10.1016/j.tet.2010.04.128

  日期：2010.6

  Described in this report is an enantioselective route toward the chamigrene natural product family. The key disconnections in our synthetic approach include sequential enantioselective decarboxylative allylation and ring-closing olefin metathesis to form the all-carbon quaternary stereocenter and spirocyclic core present in all members of this class of compounds. The generality of this strategy is demonstrated by the first total syntheses of elatol and the proposed structure of laurencenone B, as well as the first enantioselective total syntheses of laurencenone C and alpha-chamigrene. A brief exploration of the substrate scope of the enantioselective decarboxylative allylation/ring-closing metathesis sequence with fully substituted vinyl chlorides is also presented. (C) 2010 Elsevier Ltd. All rights reserved.