4,4-Dimethyl-6-methylidene-tetrahydro-2-pyranone | 92912-01-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 4,4-Dimethyl-6-methylidene-tetrahydro-2-pyranone
• 英文别名: 4,4-Dimethyl-6-methylideneoxan-2-one
• CAS: 92912-01-1
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: RLBQUVKJOWQCML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,3-Dimethyl-5-hexynoic acid 在 yellow Hg 作用下， 以 苯 为溶剂， 反应 8.0h， 以95%的产率得到4,4-Dimethyl-6-methylidene-tetrahydro-2-pyranone
  参考文献：
  名称：

  Obtention de δ-methylene δ-lactones et de δ-lactones γ-ethyleniques

  摘要：

  DOI：

  10.1016/s0040-4039(01)91002-0

文献信息

• MACROCYCLIC COMPOUNDS FOR MODULATING IL-17
  申请人：ENSEMBLE THERAPEUTICS CORPORATION

  公开号：US20150005319A1

  公开（公告）日：2015-01-01

  The invention relates generally to macrocyclic compounds of formula I and their therapeutic use. More particularly, the invention relates to macrocyclic compounds that modulate the activity of IL-17 and/or are useful in the treatment of medical conditions, such as inflammatory diseases and other IL-17-associated disorders.

  本发明涉及公式I的大环化合物及其治疗用途。更具体地，本发明涉及调节IL-17活性或用于治疗医疗情况（例如炎症性疾病和其他IL-17相关疾病）的大环化合物。
• Obtention de δ-methylene δ-lactones et de δ-lactones γ-ethyleniques
  作者：Abdelkébir Jellal、Jacques Grimaldi、Maurice Santelli

  DOI：10.1016/s0040-4039(01)91002-0

  日期：1984.1
• JELLAL, A.;GRIMALDI, J.;SANTELLI, M., TETRAHEDRON LETT., 1984, 25, N 30, 3179-3182
  作者：JELLAL, A.、GRIMALDI, J.、SANTELLI, M.

  DOI：——

  日期：——
• US9284283B2
  申请人：——

  公开号：US9284283B2

  公开（公告）日：2016-03-15
• New approaches to the synthesis of alkyl-substituted enol lactone systems, inhibitors of the serine protease elastase
  作者：Wei Dai、John A. Katzenellenbogen

  DOI：10.1021/jo00059a049

  日期：1993.3

  We have synthesized a series of alkyl-substituted enol lactones designed to act as mechanism-based inhibitors of human neutrophil elastase (HLE). General methods were developed for the preparation of alpha- and beta-alkyl-substituted 5-hexynoic acids by the bromoform reaction on the corresponding alkynoic methyl ketone, prepared by an Eschenmoser-Tanabe fragmentation sequence from a suitably substituted cyclohexenone. By this method, beta-methyl- and beta,beta-dimethyl-5-hexynoic acids were synthesized from commercially available isophorone and 3,5-dimethyl-2-cyclohexen-1-one, respectively. Alpha-Substituted 5-hexynoic acids were prepared from 3-ethoxy-2-cyclohexen-1-one, using a novel ZnCl2-mediated alkylation that we developed; this method gives high yields of alpha'-alkylation products, even with secondary halides. The most efficient method for the preparation of alpha-substituted 5-hexynoic acids involved a four-reaction sequence-alkylation of the alpha-substituted ester with 1,4-dibromobutane, elimination, bromination and bisdehydrobromination-that proceeded in high overall yield. Protio enol lactonizations were performed with mercury(II) catalysis in CH2Cl2 or CH2Cl2-H2O. Stereo-selective Z-bromo enol lactonization was carried out by Br+-induced lactonization in the presence of Ag+. E-Bromo enol lactonization with N-bromosuccinimide in CH2Cl2 in the presence of a small amount of water gave better yields and shorter reaction times than the traditional anhydrous conditions. In studies of the inhibitory activity of these lactones toward several proteases (reported in full elsewhere), we found that the alpha-alkyl-substituted protio and bromo enol lactones 1-3 were very good inhibitors of HLE, with k(a)/K(i) values ranging from 14 500 to 37 500 M-1 s-1; the beta-alkyl-substituted enol lactones 5-8 showed only moderate inhibition of HLE.