(1R,5S,8S)-8-methyl-2-methylene-8-vinyl-6-oxabicyclo[3.2.1]octan-7-one | 1039740-17-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1R,5S,8S)-8-methyl-2-methylene-8-vinyl-6-oxabicyclo[3.2.1]octan-7-one
• 英文别名: (1R,5S,8S)-8-ethenyl-8-methyl-2-methylidene-6-oxabicyclo[3.2.1]octan-7-one
• CAS: 1039740-17-4
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: FDUPRCHACUVTAF-ATZCPNFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,5S,8S)-8-methyl-2-methylene-8-vinyl-6-oxabicyclo[3.2.1]octan-7-one 在 吡啶 、 咪唑 、 叔丁基过氧化氢 、 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 selenium(IV) oxide 、 四丁基氟化铵 、 氯化二乙基铝 、 四丁基碘化铵 、 sodium hydride 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 、 水杨酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 372.83h， 生成 {(1S,2S,3R,4S,6R)-3-benzyloxymethyl-1-methoxymethoxy-3-methyl-2-vinyl-7-oxabicyclo[4.2.0]oct-4-yloxy}tert-butyldimethylsilane
  参考文献：
  名称：

  Chemoenzymatic Taxanes Approach Using Both Enantiomers of the Same Building Block. 2. Taxol CD Ring Unit

  摘要：

  The enantioselective synthesis of the Taxol CD ring unit has been achieved starting from an enantiopure building block, the enantiomer of those previously utilized in the synthesis of the A ring unit. The key features of the present synthesis are astute use of both enantiomers of the same building block and complete control in the construction of five consecutive chiral centers.

  DOI：

  10.1021/jo050039s
• 作为产物：
  描述：

  (S)-4-<(t-butyldimethylsilyl)oxy>-3-methyl-2-cyclohexenone 在 copper(I) bromide dimethylsulfide complex 、 potassium tert-butylate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 8.5h， 生成 (1R,5S,8S)-8-methyl-2-methylene-8-vinyl-6-oxabicyclo[3.2.1]octan-7-one
  参考文献：
  名称：

  Chemoenzymatic Taxanes Approach Using Both Enantiomers of the Same Building Block. 2. Taxol CD Ring Unit

  摘要：

  The enantioselective synthesis of the Taxol CD ring unit has been achieved starting from an enantiopure building block, the enantiomer of those previously utilized in the synthesis of the A ring unit. The key features of the present synthesis are astute use of both enantiomers of the same building block and complete control in the construction of five consecutive chiral centers.

  DOI：

  10.1021/jo050039s

文献信息

• A stereocontrolled approach towards highly oxygenated taxane C and CD-ring precursors
  作者：Jean-Pierre Uttaro、Gérard Audran、Jean-Marie Galano、Honoré Monti

  DOI：10.1016/s0040-4039(02)00360-x

  日期：2002.4

  Based upon a remarkable beta-face diastereoselection. a stereocontrolled construction of bicyclic systems with the appropriate stereochemical disposition of the substituents belonging either to a Baccatin-1 C-ring precursor or a Taxol(R) CD-ring precursor is reported. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Highly Efficient Stereocontrolled Synthesis of Danishefsky’s Taxol CD Ring Key Intermediate
  作者：Paul Brémond、Gérard Audran、Honoré Monti

  DOI：10.1021/jo800913x

  日期：2008.8.1

  Danishefsky's taxol CD ring key intermediate is synthesized in 15 steps and 11.4% overall yield from a readily available starting material. Absolute stereochemistry of the starting material and stereocontrolled steps determine the absolute configuration of the five requisite contiguous stereocenters.