4-[(allyloxy)ethyl]-2,2-dimethyl-1,3-dioxolane

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[(allyloxy)ethyl]-2,2-dimethyl-1,3-dioxolane
• 英文别名: 2,2-dimethyl-4-(2-prop-2-enoxyethyl)-1,3-dioxolane
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: UPYCPNFSOMHVNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(allyloxy)ethyl]-2,2-dimethyl-1,3-dioxolane 在 sodium dodecyl-sulfate 、 溴甲苯 作用下， 以 水 为溶剂， 反应 12.0h， 以93%的产率得到(+/-)-4-O-allyl-1,2,4-butanetriol
  参考文献：
  名称：

  Nascent-HBr催化去除水性表面活性剂中的正交保护基。

  摘要：

  在水环境中的有机反应最近已成为有前途的研究领域。首次描述了由分散的催化剂苄基溴的缓慢水解生成的新生HBr，其中内部水存在于含水表面活性剂中的受限胶束介质的疏水核中。持续释放的新生HBr能够以良好或极好的收率对碳水化合物，氨基醇和羟基化无环化合物中存在的酸敏感性正交官能团进行化学选择性切割。

  DOI：

  10.1021/acs.joc.9b02561
• 作为产物：
  描述：

  3-溴丙烯 、 2,2-dimethyl-4-(2-hydroxyethyl)-1,3-dioxolane 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以98%的产率得到4-[(allyloxy)ethyl]-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  Synthesis of 3‐O‐β‐D‐Glucopyranosyl‐(3R)‐hydroxybutanolide (Kinsenoside) and 3‐O‐β‐D‐Glucopyranosyl‐(3S)‐hydroxybutanolide (Goodyeroside A)

  摘要：

  The first synthesis of 3-O-beta-D-glucopyranosyl-(3R)-hydroxybutanolide (Kinsenoside) and 3-O-beta-D-glucopyranosyl-(3S)-hydroxybutanolide (Goodyeroside A) is described. The diastereomers of the aglycon in 2-O-beta-D-gulucopyranosyl-1,2,4-butanetriol derivatives, which were separable precursors of Kinsenoside and Goodyeroside A, were synthesized from optically nonactive 1,2,4-butanetriol and alpha-D-glucopyranosyl trichloroacetimidate in excellent yields.

  DOI：

  10.1081/car-200050541

文献信息

• Condensation of 1,2,4-Butanetriol with Carbonyl Compounds and Reactions of Hydroxyalkyl-1,3-dioxacyclanes
  作者：G. Z. Raskil’dina、Yu. G. Borisova、S. S. Zlotskii

  DOI：10.1134/s107036321808008x

  日期：2018.8

  3-dioxolan-4-yl)ethanol and 1,3-dioxan-4-ylmethanol was prepared by reaction of 1,2,4-butanetriol with paraformaldehyde. This mixture was subjected to O-alkylation, O-acylation, condensation with phenyl isocyanate, and substitution of OH groups for Cl. The relative activity of acetone derivatives of glycerol and 1,2,4-butanetriol in reactions with allyl chloride and benzyl chloride was estimated.

  通过使1,2,4-丁三醇与低聚甲醛反应制备2-（1,3-二氧杂戊-4-基）乙醇和1,3-二氧杂-4-基甲醇的异构体的混合物。对该混合物进行O-烷基化，O-酰化，与异氰酸苯酯缩合，以及用OH基团取代Cl。估计了甘油和1,2,4-丁三醇的丙酮衍生物在与烯丙基氯和苄基氯反应中的相对活性。
• Selective functionalization of the primary hydroxy group in triols
  作者：G. Z. Raskil’dina、V. F. Valiev、R. M. Sultanova、S. S. Zlotskii

  DOI：10.1134/s1070427215100079

  日期：2015.10

  A procedure was suggested for preparing functionally substituted 1,2-diols by O-alkylation of hydroxyalkyl-1,3-dioxacyclanes with alkyl halides, followed by acid hydrolysis. The conditions for selective cleavage of the ethers obtained were found. (2,2-Dimethyl-1,3-dioxolan-4-yl)methyl benzoate under the conditions of acid deacetalization undergoes saponification of the ester group.
• Synthesis of 3‐<i>O</i>‐β‐<scp>D</scp>‐Glucopyranosyl‐(3<i>R</i>)‐hydroxybutanolide (Kinsenoside) and 3‐<i>O</i>‐β‐<scp>D</scp>‐Glucopyranosyl‐(3<i>S</i>)‐hydroxybutanolide (Goodyeroside A)
  作者：Katsuhiko Suzuki、Nobuyuki Suzuki、Masanori Yamaura、Toyokichi Yoshizawa

  DOI：10.1081/car-200050541

  日期：2005.1

  The first synthesis of 3-O-beta-D-glucopyranosyl-(3R)-hydroxybutanolide (Kinsenoside) and 3-O-beta-D-glucopyranosyl-(3S)-hydroxybutanolide (Goodyeroside A) is described. The diastereomers of the aglycon in 2-O-beta-D-gulucopyranosyl-1,2,4-butanetriol derivatives, which were separable precursors of Kinsenoside and Goodyeroside A, were synthesized from optically nonactive 1,2,4-butanetriol and alpha-D-glucopyranosyl trichloroacetimidate in excellent yields.
• Nascent-HBr-Catalyzed Removal of Orthogonal Protecting Groups in Aqueous Surfactants
  作者：Shilpi Gupta、Smritilekha Bera、Dhananjoy Mondal

  DOI：10.1021/acs.joc.9b02561

  日期：2020.2.21

  the hydrophobic core of the confined micellar medium in aqueous surfactant is described for the first time. The sustained-release nascent-HBr enabled the chemoselective cleavages of acid-sensitive orthogonal functionalities present in carbohydrates, amino alcohols, and hydroxylated acyclic compounds in good to excellent yields.

  在水环境中的有机反应最近已成为有前途的研究领域。首次描述了由分散的催化剂苄基溴的缓慢水解生成的新生HBr，其中内部水存在于含水表面活性剂中的受限胶束介质的疏水核中。持续释放的新生HBr能够以良好或极好的收率对碳水化合物，氨基醇和羟基化无环化合物中存在的酸敏感性正交官能团进行化学选择性切割。