(2R,3R)-2,3-epoxy decanal | 1308381-98-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (2R,3R)-2,3-epoxy decanal
• 英文别名: (2R,3R)-3-heptyloxirane-2-carbaldehyde
• CAS: 1308381-98-7
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: ZAYNCWQGQVRPDV-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 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,3R)-2,3-epoxy decanal 在 Dimethylzinc 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 2.0h， 生成 9-epoxyfalcarindiol
  参考文献：
  名称：

  Total syntheses of 9-epoxyfalcarindiol and its diastereomer

  摘要：

  The first total syntheses of 9-epoxyfalcarindiol la and its diastereomer lb have been achieved. Central to our approach were the Zn-cyclopropane-based amino alcohol catalyzed enantioselective alkynylation of acrolein, the diastereoselective addition of a diynic ester to an epoxy aldehyde, and the asymmetric Sharpless epoxidation of allylic alcohol catalyzed with L-(+)-diethyl tartrate and Ti(OiPr)(4). (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.12.008
• 作为产物：
  描述：

  (2R,3R)-2,3-epoxy-1-decanol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以71%的产率得到(2R,3R)-2,3-epoxy decanal
  参考文献：
  名称：

  Total syntheses of 9-epoxyfalcarindiol and its diastereomer

  摘要：

  The first total syntheses of 9-epoxyfalcarindiol la and its diastereomer lb have been achieved. Central to our approach were the Zn-cyclopropane-based amino alcohol catalyzed enantioselective alkynylation of acrolein, the diastereoselective addition of a diynic ester to an epoxy aldehyde, and the asymmetric Sharpless epoxidation of allylic alcohol catalyzed with L-(+)-diethyl tartrate and Ti(OiPr)(4). (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.12.008

文献信息

• Organocatalytic asymmetric epoxidation and tandem epoxidation/Passerini reaction under eco-friendly reaction conditions
  作者：Anna Maria Deobald、Arlene G. Corrêa、Daniel G. Rivera、Márcio Weber Paixão

  DOI：10.1039/c2ob26247a

  日期：——

  An eco-friendly synthesis of highly functionalized epoxides and their incorporation into an organocatalytic multicomponent approach are reported. For this, a modified class of diarylprolinol silyl ethers was designed to enable high catalytic activity in an environmentally benign solvent system. The one-pot procedure showed great efficiency in promoting stereoselective multicomponent transformations in a tandem, ‘green’ fashion. Because of its non-residual, efficient and selective character, this synthetic design shows promise for large-scale applications in both diversity and target-oriented syntheses.

  报道了一种环保的高功能化环氧化物合成方法，并将其应用于有机催化多组分反应策略。为此，设计了一类改良的二芳基脯氨醇硅醚，以在环境友好的溶剂体系中实现高催化活性。该一步法程序非常有效，能够促进立体选择性多组分反应以连贯、环保的方式进行。由于其无残留、高效和选择性的特点，这种合成设计在多样的和目标导向的合成中具有大规模应用的潜力。
• Total syntheses of 9-epoxyfalcarindiol and its diastereomer
  作者：Yun Zhou、Yanli Huang、Shuoning Li、Pengfei Yang、Jiangchun Zhong、Jingwei Yin、Kaijie Ji、Yanqing Yang、Ning Ye、Lifeng Wang、Mingan Wang、Min Wang、Qinghua Bian

  DOI：10.1016/j.tetasy.2016.12.008

  日期：2017.2

  The first total syntheses of 9-epoxyfalcarindiol la and its diastereomer lb have been achieved. Central to our approach were the Zn-cyclopropane-based amino alcohol catalyzed enantioselective alkynylation of acrolein, the diastereoselective addition of a diynic ester to an epoxy aldehyde, and the asymmetric Sharpless epoxidation of allylic alcohol catalyzed with L-(+)-diethyl tartrate and Ti(OiPr)(4). (C) 2017 Elsevier Ltd. All rights reserved.