2-But-3-enyloxy-malonic acid diethyl ester | 175663-16-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-But-3-enyloxy-malonic acid diethyl ester
• 英文别名: Diethyl 2-but-3-enoxypropanedioate；diethyl 2-but-3-enoxypropanedioate
• CAS: 175663-16-8
• 化学式: C₁₁H₁₈O₅
• 分子量: 230.261
• InChiKey: YIIMEMMKOLLAEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-But-3-enyloxy-malonic acid diethyl ester 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 porcine pancreatic lipase 作用下， 以 乙醚 为溶剂， 生成 Acetic acid (R)-2-but-3-enyloxy-3-(tert-butyl-dimethyl-silanyloxy)-propyl ester
  参考文献：
  名称：

  Eight membered ethers via diene metathesis: Synthetic approach to laureatin natural products

  摘要：

  Ruthenium-mediated diene metathesis is applied to the synthesis of a range of oxocenes. The methodology is then utilised for the preparation of prelaureatin analogues. A successful synthesis of the 8-desalkyl analogue of prelaureatin in enantiomerically enriched form is described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00703-0
• 作为产物：
  描述：

  diethyl 2-hydrazonomalonate 在 manganese(IV) oxide 、 dirhodium tetraacetate 作用下， 以 氯仿 、 苯 为溶剂， 反应 4.0h， 生成 2-But-3-enyloxy-malonic acid diethyl ester
  参考文献：
  名称：

  Eight membered ethers via diene metathesis: Synthetic approach to laureatin natural products

  摘要：

  Ruthenium-mediated diene metathesis is applied to the synthesis of a range of oxocenes. The methodology is then utilised for the preparation of prelaureatin analogues. A successful synthesis of the 8-desalkyl analogue of prelaureatin in enantiomerically enriched form is described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00703-0

文献信息

• Antiviral acyclonucleosides and acyclonucleotides
  申请人：MERCK & CO. INC.

  公开号：EP0381531A2

  公开（公告）日：1990-08-08

  Disclosed are compounds of the formula: wherein B is related to one of the heterocyclic bases found in nucleic acid (DNA, RNA) such as a purine, a substituted purine, a pyrimidine or a substituted pyrimidine wherein the substituents on the purine or pyrimidine are selected from amino, hydroxyl, halogen, thio or alkylthiol wherein the alkyl moiety of the alkylthiol has 1 to 6 carbons; R¹ is fluorine, chlorine, hydroxy, alkoxy having 1 to 6 carbons or a phosphate group having the formula: wherein R⁴ and R⁵ are pharmaceutically acceptable cations; R² and R³ are independently hydroxy, alkoxy having 1 to 6 carbons or a phosphate group having the formula: wherein R⁴ and R⁵ hydrogen or are pharmaceutically acceptable cations; or two of R¹, R² and R³ taken together form a phosphate group having the formula: wherein R⁴ is hydrogen or a pharmaceutically acceptable cation. The compounds have antiviral activity. They are particularly effective against the herpes group of viruses with special utility against cytomegalovirus (CMV) and varicella-zoster virus (VZV), and against retroviruses such as HTLV-III.

  公开了式中的化合物： 其中 B 与核酸（DNA、RNA）中的杂环碱基之一有关，如嘌呤、取代的嘌呤、嘧啶或取代的嘧啶，其中嘌呤或嘧啶上的取代基选自氨基、羟基、卤素、硫代或烷基硫醇，其中烷基硫醇的烷基具有 1 至 6 个碳原子；R¹ 是氟、氯、羟基、具有 1 至 6 个碳原子的烷氧基或具有以下式子的磷酸基团： 其中 R⁴ 和 R⁵ 是药学上可接受的阳离子；R² 和 R³ 独立地是羟基、具有 1 至 6 个碳原子的烷氧基或具有以下式子的磷酸基团： 其中 R⁴ 和 R⁵ 氢或为药学上可接受的阳离子；或 R¹、R² 和 R³ 中的两个共同形成一个磷酸基团，其式为 其中 R⁴ 为氢或药学上可接受的阳离子。这些化合物具有抗病毒活性。它们对疱疹病毒群特别有效，对巨细胞病毒 (CMV) 和水痘-带状疱疹病毒 (VZV) 以及 HTLV-III 等逆转录病毒特别有效。
• Synthesis of inhibitors of imidazole glycerol phosphate dehydratase
  作者：Stephen D. Lindell、Christopher G. Earnshaw、Brian J. Wright (deceased)、David S. Carver、Mary J. O'Mahony、Elizabeth A. Saville-Stones

  DOI：10.1016/0960-894x(96)00076-5

  日期：1996.3

  Novel inhibitors of the newly discovered herbicide target enzyme imidazole glycerol phosphate dehydratase are described. The most potent inhibitor, compound 6 (IC50 < mu M), arose by linking a 1,2,4-triazole and phosphonic acid via a five atom chain. The use of malonate as a phosphate equivalent also gave rise to inhibitors, the best being compound 12 (IC50 similar to 6 mu M).
• Eight membered ethers via diene metathesis: Synthetic approach to laureatin natural products
  作者：Simon D. Edwards、Terence Lewis、Richard J.K. Taylor

  DOI：10.1016/s0040-4039(99)00703-0

  日期：1999.5

  Ruthenium-mediated diene metathesis is applied to the synthesis of a range of oxocenes. The methodology is then utilised for the preparation of prelaureatin analogues. A successful synthesis of the 8-desalkyl analogue of prelaureatin in enantiomerically enriched form is described. (C) 1999 Elsevier Science Ltd. All rights reserved.