ethyl 3-(1,3-dioxolan-2-yl)propionate | 86197-13-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 3-(1,3-dioxolan-2-yl)propionate
• 英文别名: ethyl 4-(ethylenedioxy)butanoate；ethyl 4,4-(ethylenedioxy)butyrate；ethyl 3-(1,3-dioxolan-2-yl)propanoate
• CAS: 86197-13-9
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: SRBMYZYTVOAXBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  ethyl 3-(1,3-dioxolan-2-yl)propionate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以57%的产率得到1,3-二氧戊环-2-丙-1-醇
  参考文献：
  名称：

  Synthesis of .DELTA.3-1-methylene-1-carbacephems

  摘要：

  The total synthesis of (+/-)-1-methylene-2,2- dimethyl-7-amino-1-carbacephem-4-carboxylic acid (1) is described. The reaction scheme was essentially that described by Christensen et al. for the synthesis of (+/-)-1-carbacephems. In vitro antibacterial activities of the 7-phenoxyacetyl and 7-D-alpha-phenylglycyl derivatives of 1 were compared with those of 7-(phenoxyacetamido)desacetoxycephalosporanic acid and cefalexin. Derivatives of 1 were 2-4 times less active against most of the sensitive organisms than the corresponding 7-aminodesacetoxycephalosporanic acid analogues. The activity of the 7-D-alpha-phenylglycyl derivative of 1 however was about 20 times lower than that of cefalexin when measured against Staphylococcus aureus ATCC 6538P.

  DOI：

  10.1021/jm00155a013
• 作为产物：
  描述：

  4-羟基丁酸乙酯 在 camphor-10-sulfonic acid 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 ethyl 3-(1,3-dioxolan-2-yl)propionate
  参考文献：
  名称：

  Synthetic applications of N-acylamino-1,3-dienes. 10. Importance of allylic interactions and stereoelectronic effects in dictating the steric course of the reaction of iminium ions with nucleophiles. An efficient total synthesis of (.+-.)-gephyrotoxin

  摘要：

  DOI：

  10.1021/ja00354a031

文献信息

• Dibromo-BODIPY as an Organic Photocatalyst for Radical–Ionic Sequences
  作者：William H. García-Santos、Javier Ordóñez-Hernández、Mónica Farfán-Paredes、Hiram M. Castro-Cruz、Norma A. Macías-Ruvalcaba、Norberto Farfán、Alejandro Cordero-Vargas

  DOI：10.1021/acs.joc.1c01598

  日期：2021.12.3

  A new dibrominated 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) is reported as a new metal-free photocatalyst. This BODIPY showed similar optoelectronic, electrochemical, and performance properties to those of Ru(bpy)3Cl2, one of the most common photocatalysts in a known radical–ionic transformation, such as the formation of 1,4-dicarbonyl compounds. Moreover, additional sequences in which the

  一种新的二溴化 4,4-二氟-4-bora-3a,4a- diaza - s - indacene (BODIPY) 被报道为一种新的无金属光催化剂。该 BODIPY 显示出与 Ru(bpy) 3 Cl 2相似的光电、电化学和性能特性，Ru(bpy) 3 Cl 2是已知自由基 - 离子转化（例如形成 1,4-二羰基化合物）中最常见的光催化剂之一。此外，使用这种 BODIPY 光催化剂开发了额外的序列，其中生成的氧离子被内部亲核试剂捕获。这些新序列允许直接制备 γ-烷氧基内酯、单保护的 1,4-酮醛和二氢呋喃。这种新的催化剂、方法和伪造的官能团可能是有机合成中的重要工具。
• Synthesis of (<i>E</i>)-4-Oxo-5-hexenals and Their Acetal Derivatives
  作者：Shuji Kanemasa、Tatsuya Otsuka、Kenji Doi、Otohiko Tsuge、Eiji Wada

  DOI：10.1055/s-1990-27125

  日期：——

  An effective synthesis of (E)-4-oxo-5-hexenals 6 and the acetals 5 starting from ethyl 2-alkoxy-1-cyclopropanecarboxylates 1a-d is presented. The acid-induced ring opening of the cyclopropanecarboxylates 1a, b, followed by phosphorylmethylation or the phosphorylmethylation of the ester 1c followed by ring opening leads to the 5-acetal of 2,5-dioxopentylphosphonate 4. The Horner-Emmons olefination of 4 with various aldehydes produces the title compounds.

  本研究展示了一种从乙基2-烷氧基-1-环丙烷羧酸酯1a-d出发，合成(E)-4-氧-5-己烯醛6及其缩醛5的有效方法。首先，环丙烷羧酸酯1a、b在酸性诱导下环开裂，随后进行膦甲基化，或者先对酯1c进行膦甲基化后环开裂，得到2,5-二氧戊基膦酸酯的5-缩醛4。通过Horner-Emmons烯化反应，4与各种醛反应，生成目标化合物。
• Practical β-masked formylation and acetylation of electron-deficient olefins utilizing tetra(n-butyl)ammonium peroxydisulfate
  作者：Jae Chul Jung、Yong Hae Kim、Kieseung Lee

  DOI：10.1016/j.tetlet.2011.06.116

  日期：2011.9

  Various electron-deficient olefins reacted readily with 1,3-dioxolane or 2-methyl-1,3-dioxlane in the presence of TBAP to afford the corresponding 1,3-dioxolanylated or 2-methyl-1,3-dioxolanylated products in a complete regioselective manner in good to excellent yields. (C) 2011 Elsevier Ltd. All rights reserved.
• KANEMASA, SHUJI;OTSUKA, TATSUYA;DOI, KENJI;TSUGE, OTOHIKO;WADA, EIJI, SYNTHESIS,(1990) N2, C. 1167-1169
  作者：KANEMASA, SHUJI、OTSUKA, TATSUYA、DOI, KENJI、TSUGE, OTOHIKO、WADA, EIJI

  DOI：——

  日期：——
• Synthesis of .DELTA.3-1-methylene-1-carbacephems
  作者：Piet Herdewijn、Paul J. Claes、Hubert Vanderhaeghe

  DOI：10.1021/jm00155a013

  日期：1986.5

  The total synthesis of (+/-)-1-methylene-2,2- dimethyl-7-amino-1-carbacephem-4-carboxylic acid (1) is described. The reaction scheme was essentially that described by Christensen et al. for the synthesis of (+/-)-1-carbacephems. In vitro antibacterial activities of the 7-phenoxyacetyl and 7-D-alpha-phenylglycyl derivatives of 1 were compared with those of 7-(phenoxyacetamido)desacetoxycephalosporanic acid and cefalexin. Derivatives of 1 were 2-4 times less active against most of the sensitive organisms than the corresponding 7-aminodesacetoxycephalosporanic acid analogues. The activity of the 7-D-alpha-phenylglycyl derivative of 1 however was about 20 times lower than that of cefalexin when measured against Staphylococcus aureus ATCC 6538P.