(4R,5R,2E)-4,5-isopropylidenedioxyundec-2-ene-1-ol | 1132793-38-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R,2E)-4,5-isopropylidenedioxyundec-2-ene-1-ol
• 英文别名: (E)-3-[(4R,5R)-5-hexyl-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol
• CAS: 1132793-38-4
• 化学式: C₁₄H₂₆O₃
• 分子量: 242.359
• InChiKey: DRAZTJXSVPMKGL-AXCOZDIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  原乙酸三甲酯 、 (4R,5R,2E)-4,5-isopropylidenedioxyundec-2-ene-1-ol 在 丙酸 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 4.0h， 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：

  (4R,5R,2E)-ethyl 4,5-isopropylidenedioxyundec-2-enoate 在 二异丁基氢化铝 、 水 、 rochelle salt 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 6.0h， 以97%的产率得到(4R,5R,2E)-4,5-isopropylidenedioxyundec-2-ene-1-ol
  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

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.