allyl 4,4-dimethyl-3-oxopentanoate | 180511-99-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: allyl 4,4-dimethyl-3-oxopentanoate
• 英文别名: 2-Propen-1-yl 4,4-dimethyl-3-oxopentanoate；prop-2-enyl 4,4-dimethyl-3-oxopentanoate
• CAS: 180511-99-3
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: MXOYHQXBGDHPPY-UHFFFAOYSA-N

物化性质

• 沸点：
  239.2±15.0 °C(Predicted)
• 密度：
  0.972±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  allyl 4,4-dimethyl-3-oxopentanoate 在 palladium on activated charcoal 四氢吡咯 、 四(三苯基膦)钯 、 氢气 、 sodium hydride 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， -60.0~25.0 ℃ 、101.33 kPa 条件下， 反应 13.0h， 生成 (2R,5S)-2-(3,3-dimethyl-2-oxobutyl)-6,6-dimethyl-5-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxoheptanoic acid
  参考文献：
  名称：

  Peptidomimetic Inhibitors of Herpes Simplex Virus Ribonucleotide Reductase with Improved in Vivo Antiviral Activity

  摘要：

  We have been investigating the potential of a new class of antiviral compounds. These peptidomimetic derivatives prevent association of the two subunits of herpes simplex virus (HSV) ribonucleotide reductase (RR), an enzyme necessary for efficient replication of viral DNA. The compounds disclosed in this paper build on our previously published work. Structure-activity studies reveal beneficial modifications that result in improved antiviral potency in cell culture in a murine ocular model of HSV-induced keratitis. These modifications include a stereochemically defined (2,6-dimethylcyclohexyl)amino N-terminus, two ketomethylene amide bond isosteres, and a (1-ethylneopentyl)amino C-terminus. These three modifications led to the preparation of BILD 1351, our most potent antiherpetic agent containing a ureido N-terminus. Incorporation of the C-terminal modification into our inhibitor series based on a (phenylpropionyl)valine N-terminus provided BILD 1357, a significantly more potent antiviral compound than our previously published best compound, BILD 1263.

  DOI：

  10.1021/jm960324r
• 作为产物：
  描述：

  乙酸烯丙酯 、 三甲基乙酰氯 在 lithium hexamethyldisilazane 作用下， 生成 allyl 4,4-dimethyl-3-oxopentanoate
  参考文献：
  名称：

  Peptidomimetic Inhibitors of Herpes Simplex Virus Ribonucleotide Reductase with Improved in Vivo Antiviral Activity

  摘要：

  We have been investigating the potential of a new class of antiviral compounds. These peptidomimetic derivatives prevent association of the two subunits of herpes simplex virus (HSV) ribonucleotide reductase (RR), an enzyme necessary for efficient replication of viral DNA. The compounds disclosed in this paper build on our previously published work. Structure-activity studies reveal beneficial modifications that result in improved antiviral potency in cell culture in a murine ocular model of HSV-induced keratitis. These modifications include a stereochemically defined (2,6-dimethylcyclohexyl)amino N-terminus, two ketomethylene amide bond isosteres, and a (1-ethylneopentyl)amino C-terminus. These three modifications led to the preparation of BILD 1351, our most potent antiherpetic agent containing a ureido N-terminus. Incorporation of the C-terminal modification into our inhibitor series based on a (phenylpropionyl)valine N-terminus provided BILD 1357, a significantly more potent antiviral compound than our previously published best compound, BILD 1263.

  DOI：

  10.1021/jm960324r

文献信息

• Decarboxylative Aldol Reactions of Allyl β-Keto Esters via Heterobimetallic Catalysis
  作者：Sha Lou、John A. Westbrook、Scott E. Schaus

  DOI：10.1021/ja045981k

  日期：2004.9.1

  Mild and selective heterobimetallic-catalyzed decarboxylative aldol reactions involving allyl beta-keto esters have been developed. The reaction is promoted by Pd(0)- and Yb(III)-DIOP complexes at room temperature and involves the in situ formation of a ketone enolate from allyl beta-keto esters followed by addition of the enolate to aldehydes. The reaction is a new example of heterobimetallic catalysis

  涉及烯丙基β-酮酯的温和且选择性的杂双金属催化的脱羧醛醇反应已被开发。该反应在室温下由 Pd(0)-和 Yb(III)-DIOP 配合物促进，包括由烯丙基 β-酮酯原位形成酮烯醇化物，然后将烯醇化物加入醛。该反应是异双金属催化的一个新例子，其中优化的反应条件需要添加两种金属。
• US4146632A
  申请人：——

  公开号：US4146632A

  公开（公告）日：1979-03-27
• US4155999A
  申请人：——

  公开号：US4155999A

  公开（公告）日：1979-05-22
• US4163052A
  申请人：——

  公开号：US4163052A

  公开（公告）日：1979-07-31
• Peptidomimetic Inhibitors of Herpes Simplex Virus Ribonucleotide Reductase with Improved <i>in Vivo</i> Antiviral Activity
  作者：Neil Moss、Pierre Beaulieu、Jean-Simon Duceppe、Jean-Marie Ferland、Michel Garneau、Jean Gauthier、Elise Ghiro、Sylvie Goulet、Ingrid Guse、Jorge Jaramillo、Montse Llinas-Brunet、Éric Malenfant、Raymond Plante、Martin Poirier、Francois Soucy、Dominik Wernic、Christiane Yoakim、Robert Déziel

  DOI：10.1021/jm960324r

  日期：1996.1.1

  We have been investigating the potential of a new class of antiviral compounds. These peptidomimetic derivatives prevent association of the two subunits of herpes simplex virus (HSV) ribonucleotide reductase (RR), an enzyme necessary for efficient replication of viral DNA. The compounds disclosed in this paper build on our previously published work. Structure-activity studies reveal beneficial modifications that result in improved antiviral potency in cell culture in a murine ocular model of HSV-induced keratitis. These modifications include a stereochemically defined (2,6-dimethylcyclohexyl)amino N-terminus, two ketomethylene amide bond isosteres, and a (1-ethylneopentyl)amino C-terminus. These three modifications led to the preparation of BILD 1351, our most potent antiherpetic agent containing a ureido N-terminus. Incorporation of the C-terminal modification into our inhibitor series based on a (phenylpropionyl)valine N-terminus provided BILD 1357, a significantly more potent antiviral compound than our previously published best compound, BILD 1263.