(2R,3S)-(–)-epoxyfarnesal | 1196980-68-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2R,3S)-(–)-epoxyfarnesal
• 英文别名: (2R,3S)-3-[(3E)-4,8-dimethylnona-3,7-dienyl]-3-methyloxirane-2-carbaldehyde
• CAS: 1196980-68-3
• 化学式: C₁₅H₂₄O₂
• 分子量: 236.354
• InChiKey: JGVHFKXHMXWLAM-FQSSWDBKSA-N

物化性质

• 溶解度：
  可溶于二氯甲烷、DMSO、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3S)-(–)-epoxyfarnesal 在 bis(1,5-cyclooctadiene)nickel (0) 、 (triphenylphosphine)copper(I) hydride hexamer 、 苯硅烷 、 二异丁基氢化铝 、 三环己基膦 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.5h， 生成
  参考文献：
  名称：

  Total syntheses of the squalene-derived halogenated polyethers ent -dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades

  摘要：

  Herein we describe in full our investigations leading to the first total syntheses of ent-dioxepandehydrothyrsiferol and armatol A. Discovery of a bromonium-initiated epoxide-opening cascade enabled novel tactics for constructing key fragments found in both natural products and have led us to revise the proposed biogeneses. Other common features found in the routes include convergent fragment coupling strategies to assemble the natural products' backbones and the use of epoxide-opening cascades for rapid constructions of the fused polyether subunits. Through de novo synthesis of armatol A, we elucidate the absolute and relative configuration of this natural product. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.041
• 作为产物：
  描述：

  2,3-epoxy-trans,trans-farnesol 在 三氧化硫吡啶 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以90 %的产率得到(2R,3S)-(–)-epoxyfarnesal
  参考文献：
  名称：

  ent-Stachybotrin C及其同系物的不对称全合成

  摘要：

  ent -stachybotrin C 及其同系物的不对称全合成已分别通过市售材料以 12 个步骤的最长线性序列的收敛方法完成。值得注意的合成转变涉及级联 Knoevenagel 缩合/Hantzsch 酯还原/环氧化物开环/醚交换，以构建具有两个相邻立构中心的核心吡喃环。

  DOI：

  10.1021/acs.orglett.4c00380

文献信息

• Structure Determination of a New Juvenile Hormone from a Heteropteran Insect
  作者：Toyomi Kotaki、Tetsuro Shinada、Kanako Kaihara、Yasufumi Ohfune、Hideharu Numata

  DOI：10.1021/ol902161x

  日期：2009.11.19

  The structure of the juvenile hormone (JH) in the suborder Heteroptera, order Hemiptera, has been known for a very long time to be different from the JH of other orders, but the structure has been a matter of controversy. The structure was first elucidated by an unprecedented approach involving the screening of a JH molecular library. The novel Heteroptera-specific JH (JHSB(3)) is a new category of JH that is featured by the skipped bisepoxide structure.
• Total syntheses of the squalene-derived halogenated polyethers ent -dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades
  作者：Brian S. Underwood、Jessica Tanuwidjaja、Sze-Sze Ng、Timothy F. Jamison

  DOI：10.1016/j.tet.2013.04.041

  日期：2013.6

  Herein we describe in full our investigations leading to the first total syntheses of ent-dioxepandehydrothyrsiferol and armatol A. Discovery of a bromonium-initiated epoxide-opening cascade enabled novel tactics for constructing key fragments found in both natural products and have led us to revise the proposed biogeneses. Other common features found in the routes include convergent fragment coupling strategies to assemble the natural products' backbones and the use of epoxide-opening cascades for rapid constructions of the fused polyether subunits. Through de novo synthesis of armatol A, we elucidate the absolute and relative configuration of this natural product. (C) 2013 Elsevier Ltd. All rights reserved.
• Asymmetric Total Syntheses of <i>ent</i>-Stachybotrin C and Its Congener
  作者：Zhipeng Xie、Shengfu Duan、Haodong Wang、Tingyan Li、Zhixiang Xie

  DOI：10.1021/acs.orglett.4c00380

  日期：2024.4.19

  The asymmetric total syntheses of ent-stachybotrin C and its congener have been accomplished through a convergent approach in the longest linear sequence of 12 steps from commercially available materials, respectively. Noteworthy transformation of the synthesis involved a cascade Knoevenagel condensation/Hantzsch ester reduction/epoxide ring-opening/transetherification to construct the core pyran ring

  ent -stachybotrin C 及其同系物的不对称全合成已分别通过市售材料以 12 个步骤的最长线性序列的收敛方法完成。值得注意的合成转变涉及级联 Knoevenagel 缩合/Hantzsch 酯还原/环氧化物开环/醚交换，以构建具有两个相邻立构中心的核心吡喃环。