2-Nonanone, 4-(acetyloxy)-3-methylene- | 268226-97-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Nonanone, 4-(acetyloxy)-3-methylene-
• 英文别名: (3-methylidene-2-oxononan-4-yl) acetate
• CAS: 268226-97-7
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: DIQKMCVVKUZMCN-UHFFFAOYSA-N

物化性质

• 沸点：
  305.1±25.0 °C(Predicted)
• 密度：
  0.954±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  2-Nonanone, 4-(acetyloxy)-3-methylene- 在 sodium hydroxide 、 水 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 48.17h， 生成 3-Hex-(E)-ylidene-hexane-2,5-dione
  参考文献：
  名称：

  A Simplified Route to (E)-2-Alkylidene-1,4-diketones

  摘要：

  在THF中，存在NaOH（0.6 N）的情况下，硝基烷对烯丙基Baylis-Hillman醋酸酯1进行共轭加成，得到具有完整立体选择性的2-烷基亚烯基-4-硝基酮2，随后通过Nef反应进一步转化为相应的1,4-二酮3，产率从中等到良好。

  DOI：

  10.1055/s-2000-6257

文献信息

• Regioselective synthesis of 1,2,4,5-tetrasubstituted pyridines from Baylis–Hillman adducts via consecutive [3+2+1] annulation protocol
  作者：Sung Hwan Kim、Ko Hoon Kim、Hoo Sook Kim、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2008.01.110

  日期：2008.3

  An efficient synthetic method of poly-substituted pyridines was developed. Various poly-substituted pyridines were prepared from the combination of Baylis–Hillman adducts (3 carbons), activated methylene compounds (2 carbons) and ammonium acetate (1 nitrogen) via [3+2+1] annulation protocol in good yields, regioselectively.

  开发了一种高效的多取代吡啶合成方法。通过[3 + 2 + 1]环化方案，从Baylis-Hillman加合物（3个碳），活化的亚甲基化合物（2个碳）和乙酸铵（1个氮）的组合中，以区域选择性高收率制备了各种多取代的吡啶。
• Diels–Alder dimerization of Morita–Baylis–Hillman acetates catalyzed by organocatalysts
  作者：Hong-Ping Deng、Yin Wei、Min Shi

  DOI：10.1007/s11164-012-0626-6

  日期：2013.1

  DABCO-catalyzed dimerization of Morita–Baylis–Hillman acetates to synthesize a series of 3-alkyl-4-(E)-alkenyl-cyclohex-1-ene-1,4-dicarbonyl compounds in excellent yields with modest to excellent diastereoselectivity is reported. A plausible reaction mechanism is also proposed on the basis of previous literature and preliminary investigation the asymmetric version of the reaction.

  据报道，DABCO催化Morita–Baylis–Hillman乙酸酯的二聚反应，以优异的收率和适度至优异的非对映选择性合成了一系列3-烷基-4-（E）-烯基-环己-1-烯-1,4-二羰基化合物。在先前的文献和对反应的不对称形式的初步研究的基础上，还提出了合理的反应机理。
• An Efficient Synthesis of Poly-Substituted Phenols and Pyridines from Morita-Baylis-Hillman Acetates and Diethyl Oxalacetate
  作者：Jin Yu、Ko Hoon Kim、Hyun Ju Lee、Jae Nyoung Kim

  DOI：10.5012/bkcs.2013.34.10.3027

  日期：2013.10.20

  Various phenol derivatives were synthesized in a one-pot reaction from MBH acetates and sodium diethyl oxalacetate via a [4C+2C] cyclization protocol. In addition, some pyridine derivatives could also be synthesized using the same starting materials, by isolating the $S_N2^\prime}$ reaction intermediate and performing the cyclization with $NH_4OAc$.

  通过[4C+2C]环化协议，以 MBH 乙酸酯和草酰乙酸钠为原料，在一次反应中合成了多种苯酚衍生物。此外，通过分离 $S_N2^\prime}$ 反应中间体并与 $NH_4OAc$ 进行环化反应，还可以使用相同的起始原料合成一些吡啶衍生物。
• Synthesis of 3-Alkylidenebicyclo[3.2.1]octan-8-oneSkeleton from the Baylis-Hillman Acetates
  作者：Jae Nyoung Kim、Jeong Mi Kim、Ka Young Lee

  DOI：10.1055/s-2003-38750

  日期：——

  Synthesis of 3-alkylidenebicyclo[3.2.1]octan-8-one skeleton 4 from Baylis-Hillman acetates 1 was carried out under kinetically controlled conditions: K 2 CO 3 in ethanol at room temperature.

  从 Baylis-Hillman 醋酸盐 1 合成 3-亚烷基双环 [3.2.1]octan-8-one 骨架 4 在动力学控制条件下进行：K 2 CO 3 在乙醇中室温。
• Regioselective synthesis of polysubstituted phenol derivatives from Baylis–Hillman adducts via [3+3] annulation strategy
  作者：Da Yeon Park、Seong Jin Kim、Taek Hyeon Kim、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2006.06.147

  日期：2006.8

  Polysubstituted phenol derivatives were synthesized from the acetates of Baylis-Hillman adducts and dimethyl 1,3-acetonedicarboxylate (DMAD) in a one-pot reaction via the sequential SNT reaction, aldol condensation, and 1,3-H shift process. (c) 2006 Elsevier Ltd. All rights reserved.