methyl 6-oxo-2-hexenoate | 146346-37-4

• 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: methyl 6-oxo-2-hexenoate
• 英文别名: methyl 6-hydroxyhex-2-enoate；Methyl 6-hydroxyhex-2-enoate
• CAS: 146346-37-4
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: ATLBQTPBCVSZGU-UHFFFAOYSA-N

物化性质

• 沸点：
  238.7±23.0 °C(Predicted)
• 密度：
  1.039±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 6-oxo-2-hexenoate 在 4 A molecular sieve 、 potassium tert-butylate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 1.5h， 生成 methyl (E)-6-hydroxy-7-nitro-2-octenoate
  参考文献：
  名称：

  Tandem inter [4+2]/intra [3+2] nitroalkene cycloadditions. 4. Cycloadditions with (E)- and (Z)-1-propenyl ethers

  摘要：

  The tandem [4 + 2]/[3 + 2] cycloaddition of nitroalkene 1 was initiated efficiently by 1-propenyl ethers as the dienophile. Ethyl(E)-1-propenyl ether reacted highly selectively to give a single nitro so acetal cycloadduct 6. Hydrogenolysis of 6 afforded a single isomer of alpha-hydroxy lactam 8 wherein the newly installed methyl group occupied the beta-configuration. Similarly, ethyl(Z)-1-propenyl ether produced an anomeric mixture of cycloadducts 7a and 7b which afforded a single alpha-hydroxy lactam 9 upon hydrogenolysis. The methyl group in 9 occupied the alpha-orientation. The high and complementary selectivity for production of 8 and 9 was explained on the basis of an extreme endo preference for the ethoxy group of the 1-propenyl ether in the [4 + 2] cycloaddition.

  DOI：

  10.1021/jo00059a043

文献信息

• Stereoselective Radical Carbon−Carbon Bond Forming Reactions of β-Alkoxy Esters:  Atom and Group Transfer Allylations under Bidentate Chelation Controlled Conditions
  作者：Y. Guindon、B. Guérin、C. Chabot、W. Ogilvie

  DOI：10.1021/ja9541241

  日期：1996.1.1

  The radical allylation of a series of beta-alkoxy esters using allyltrimethylsilane in the presence of MgBr2 . OEt(2) is described. Under bidentate chelation-controlled conditions, allyltrimethylsilane rivals allyltributyltin in efficiency and is a superior reagent from ecological and practical perspectives. The reactions work with iodides and bromides as well as phenylselenides. The isolation of gamma-phenylseleno intermediates indicates that the reaction proceeds by an atom transfer process. These reactions require initiation with Et(3)B and can be inhibited by galvinoxyl, m- and p-dinitrobenzene indicating that this atom transfer sequence involves the intermediacy of radicals.
• Rate enhancement in the Wacker oxidation of hydroxy-α,β-unsaturated esters: A fast neutral method for the preparation of masked β-ketoesters
  作者：Simon X Auclair、Michelle Morris、Michael A. Sturgess

  DOI：10.1016/0040-4039(93)88033-f

  日期：1992.12