(E)-2,4-Dimethyl-3-oxo-hept-4-enoic acid benzyl ester | 75630-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-2,4-Dimethyl-3-oxo-hept-4-enoic acid benzyl ester
• 英文别名: benzyl (E)-2,4-dimethyl-3-oxohept-4-enoate
• CAS: 75630-84-1
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: QMZKOMUXXIFMCK-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (E)-2,4-Dimethyl-3-oxo-hept-4-enoic acid benzyl ester 以85%的产率得到
  参考文献：
  名称：

  NAKATA TADASHI; OISHI TAKESHI, TETRAHEDRON LETT., 1980, 21, NO 17, 1641-1644

  摘要：

  DOI：

文献信息

• Stereoselective reduction of β-keto esters with zinc borohydride. stereoselective synthesis of -3-hydroxy-2-alkylpropionates
  作者：Tadashi Nakata、Takeshi Oishi

  DOI：10.1016/s0040-4039(00)77774-4

  日期：1980.1

  -3-hydroxy-2-alkylpropionates were prepared in high stereoselectivity and in high isolated yield by zinc borohydride reduction of the corresponding β-keto esters.

  通过相应的β-酮酯的硼氢化锌还原，以高的立体选择性和高的分离产率制备了-3-羟基-2-烷基丙酸酯。
• Methods
  申请人：Sattentau James Quentin

  公开号：US20070110759A1

  公开（公告）日：2007-05-17

  The presence of aldehydic groups on proteins and lipoproteins is associated with various pathological conditions such as atherosclerosis, diabetes and alcoholic liver disease. Respiratory syncytial virus (RSV) is a major cause of severe respiratory disease in infants and the elderly. RSV vaccine research has been impeded because a formalin-inactivated vaccine used in the 1960s predisposed infants to enhanced disease following subsequent natural infection. The molecular basis for the vaccine-induced hypersensitivity has not, however, been elucidated. We show here that addition of reactive carbonyl groups to ovalbumin (OVA) by treatment with glycolaldehyde or formaldehyde increases the protein's immunogenicity in mice, and biases the immune response towards a Th2-type response. The increased immunogenicity and the Th2-type response can both be abrogated by reductive elimination of the reactive carbonyl groups. We demonstrate that RSV inactivated by formaldehyde (FI-RSV), following a protocol used previously to prepare the vaccine, contains reactive carbonyl groups. Using a well-established model of FI-RSV vaccine-induced pathology, immunisation of mice with FI-RSV and subsequent challenge of the mice with live RSV induced Th2-type responses, lung eosinophilia and weight loss that were abrogated by reductive elimination of the reactive carbonyl groups. We thus propose that the addition of reactive carbonyl groups to RSV during inactivation is the major mechanism that drives the Th2-immune response and associated pathology. Moreover, we suggest that the addition of reactive carbonyl groups to other antigens, including vaccines, may be responsible for other hypersensitive and allergic reactions described in the literature.