(2S,3R)-ethyl 2,3-isopropylidenedioxyheptanoate | 1132793-33-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R)-ethyl 2,3-isopropylidenedioxyheptanoate
• 英文别名: ethyl (4S,5R)-5-butyl-2,2-dimethyl-1,3-dioxolane-4-carboxylate
• CAS: 1132793-33-9
• 化学式: C₁₂H₂₂O₄
• 分子量: 230.304
• InChiKey: MSSFECWWAGEAMB-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  (2S,3R)-ethyl 2,3-isopropylidenedioxyheptanoate 在 二异丁基氢化铝 、 甲醇 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 3.25h， 生成
  参考文献：
  名称：

  Synthesis of β,γ-disubstituted-γ-lactones through a Johnson–Claisen rearrangement: a short route to xylobovide, nor-canadensolide, canadensolide, sporothriolide and santolinolide

  摘要：

  The Johnson-Claisen rearrangement of allyl alcohols with chiral vicinal diol functionality was employed to access chiral beta,gamma-disubstituted-gamma-lactones in high enantio- and diastereoselectivity. These were efficiently converted into nor-canadensolide, the advanced gamma-(lactone-lactol) intermediate for xylobovide, canadensolide and sporothriolide and the lactone moiety of the santolinolides. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.018
• 作为产物：
  描述：

  (2S,3R)-ethyl-2,3-dihydroxyheptanoate 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以98%的产率得到(2S,3R)-ethyl 2,3-isopropylidenedioxyheptanoate
  参考文献：
  名称：

  Chiral vicinal diols as platforms for separable diastereomers in Johnson–Claisen rearrangement: a new short route to (−)-nor-canadensolide, (−)-canadensolide and (−)-sporothriolide

  摘要：

  The chiral vicinal diols prepared by asymmetric dihydroxylation in high enantioselectivities provide an excellent platform for separable diastereomers in the Johnson-Claisen rearrangement. The separated syn-diastereomers were converted into the advanced gamma-(lactone-lactol) intermediates (in six steps, 26-27% overall yields) for the synthesis of (-)-nor-canadensoiide, (-)-canadensolide and (-)-sporothriolide. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.084

文献信息

• Synthesis of β,γ-disubstituted-γ-lactones through a Johnson–Claisen rearrangement: a short route to xylobovide, nor-canadensolide, canadensolide, sporothriolide and santolinolide
  作者：Rodney A. Fernandes、Arun B. Ingle、Vijay P. Chavan

  DOI：10.1016/j.tetasy.2009.11.018

  日期：2009.12

  The Johnson-Claisen rearrangement of allyl alcohols with chiral vicinal diol functionality was employed to access chiral beta,gamma-disubstituted-gamma-lactones in high enantio- and diastereoselectivity. These were efficiently converted into nor-canadensolide, the advanced gamma-(lactone-lactol) intermediate for xylobovide, canadensolide and sporothriolide and the lactone moiety of the santolinolides. (C) 2009 Elsevier Ltd. All rights reserved.
• SATO TOSHIO; TSURUMAKI MASAJI; FUJISAWA TAMOTSU, CHEM. LETT.,(1986) N 8, 1367-1370
  作者：SATO TOSHIO、 TSURUMAKI MASAJI、 FUJISAWA TAMOTSU

  DOI：——

  日期：——
• Chiral vicinal diols as platforms for separable diastereomers in Johnson–Claisen rearrangement: a new short route to (−)-nor-canadensolide, (−)-canadensolide and (−)-sporothriolide
  作者：Rodney A. Fernandes、Arun B. Ingle

  DOI：10.1016/j.tetlet.2008.12.084

  日期：2009.3

  The chiral vicinal diols prepared by asymmetric dihydroxylation in high enantioselectivities provide an excellent platform for separable diastereomers in the Johnson-Claisen rearrangement. The separated syn-diastereomers were converted into the advanced gamma-(lactone-lactol) intermediates (in six steps, 26-27% overall yields) for the synthesis of (-)-nor-canadensoiide, (-)-canadensolide and (-)-sporothriolide. (C) 2009 Elsevier Ltd. All rights reserved.