(3E,7E)-deca-3,7-diene-2,9-dione | 138879-01-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3E,7E)-deca-3,7-diene-2,9-dione
• CAS: 138879-01-3
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: MTJCWONYZOGINU-KQQUZDAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3E,7E)-deca-3,7-diene-2,9-dione 在 盐酸 、 三苯基氯甲烷 、 tin(ll) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (1α,3aβ,7aβ)-1-(1-oxoethyl)-5-methyl-2,3,3a,4-tetrahydro-1H-7(7aH)-indenone
  参考文献：
  名称：

  Silyl group-transfer-mediated serial Michael additions

  摘要：

  Three protocols have been developed for achieving ordered, multiple (serial) Michael reactions initiated by silyl enol ethers or silyl ketene acetals. Anion (fluoride or m-chlorobenzoate) catalysis was most effective for reactions of silyl ketene acetal 2 with bis diesters, as in the highly selective formation of 3. Lewis acid (ZnI2) catalysis was more general than anion catalysis and afforded stereochemically complementary products with lower selectivity. The use of SnCl2-trityl chloride was effective in reactions of both silyl ketene acetals and silyl enol ethers with bis enones. Very high stereoselectivity was generally observed in the formation of cyclopentanes. The products of serial Michael reactions of bis enones could be regiospecifically cyclized to bicyclic enones. Overall, it was found that the serial Michael reactions initiated by silyl enolates can be used to form efficiently and selectively complex cyclics from simple acyclic precursors.

  DOI：

  10.1021/jo00032a026
• 作为产物：
  描述：

  1,5-已二烯 、 丁烯酮 在 M₇₃SIPr 作用下， 以 氯仿 为溶剂， 100.0 ℃ 、200.0 kPa 条件下， 反应 1.0h， 以85%的产率得到(3E,7E)-deca-3,7-diene-2,9-dione
  参考文献：
  名称：

  Step-Economical Access to Valuable Weinreb Amide 2,5-Disubstituted Pyrrolidines by a Sequential One-Pot Two-Directional Cross-Metathesis/Cyclizing Aza-Michael Process

  摘要：

  Double cross-metathesis of 1,5-hexadiene with a variety of electron-deficient alkenes including the reluctant Weinreb acrylamide has been successfully accomplished. It was found that the process is quite general, and microwave irradiation effectively accelerates cross-coupling metathesis. This promotes a very versatile and high yielding methodology for the synthesis of symmetric Michael acceptors, which can be transformed into 2,5-disubstituted pyrrolidines through a sequential one-pot two-directional cross-metathesis/ring-closing double aza-Michael process.

  DOI：

  10.1021/jo302435a

文献信息

• A short synthetic route to the tricyclic guanidinium core of the batzelladine alkaloids
  作者：Gregory P. Black、Patrick J. Murphy、Nigel D.A. Walshe

  DOI：10.1016/s0040-4020(98)00576-6

  日期：1998.8

  addition of guanidine to a series of bis-α,β-unsaturated ketones is reported leading to the formation of tricyclic guanidines, which are models of the naturally occurring batzelladine alkaloids. Nmr evidence is given in support of a new assignment for the relative stereochemistry of batzelladine F.

  据报道，向一系列双-α，β-不饱和酮中添加胍可导致三环胍的形成，三环胍是天然巴兹拉定生物碱的模型。提供了Nmr证据来支持巴茨拉定F的相对立体化学的新任务。
• Remarkable Phosphine-Effect on the Intramolecular Aldol Reactions of Unsaturated 1,5-Diketones:  Highly Regioselective Synthesis of Cross-Conjugated Dienones
  作者：Reema K. Thalji、William R. Roush

  DOI：10.1021/ja054085l

  日期：2005.12.1

  We report a phosphine-mediated intramolecular aldol cyclization of unsaturated diketones that proceeds with extremely high levels of regioselectivity for the cross-conjugated bicyclic dienone products. The sense of regioselectivity observed in this reaction is complementary to that obtained using traditional aldol conditions. Experimental evidence that supports the involvement of a phosphine Michael

  我们报告了膦介导的不饱和二酮的分子内羟醛环化，其对交叉共轭双环二烯酮产物具有极高的区域选择性。在该反应中观察到的区域选择性与使用传统羟醛条件获得的区域选择性互补。描述了支持参与膦迈克尔加合物的实验证据。
• Extended Stereocontrol in Silyl Group-Transfer Cyclizations: Control of Four Contiguous Chiral Centers
  作者：Peter G. Klimko、Daniel A. Singleton

  DOI：10.1055/s-1994-25618

  日期：——

  The potential for extended stereocontrol in silyl group-transfer cyclizations was explored in model studies which formed four contiguous chiral centers. The diastereofacial selectivity for the reaction of cyclized intermediates was outstanding for both fluoride and SnCl2 trityl chloride mediated reactions. Good simple diastereoselectivity was observed in reactions initiated by prochiral silyl enolates.

  在形成四个连续手性中心的模型研究中探索了甲硅烷基转移环化中扩展立体控制的潜力。对于氟化物和 SnCl2 三苯甲基氯介导的反应，环化中间体反应的非对映选择性都很突出。 在前手性甲硅烷基烯醇化物引发的反应中观察到良好的简单非对映选择性。
• The first report of Lewis acid reagents in the intramolecular Rauhut–Currier reaction
  作者：Andrew T. Krasley、William P. Malachowski

  DOI：10.1016/j.tetlet.2015.09.069

  日期：2015.10

  report of Lewis acid use in intramolecular Rauhut–Currier reactions is described. Titanium Lewis acids lead to rapid Rauhut–Currier reactions in the case of two classic substrates. More importantly, titanium and tin Lewis acids were the only successful reagent for a more complex substrate, thereby illustrating the potential for Lewis acid reagents to facilitate challenging intramolecular Rauhut–Currier

  描述了路易斯酸在分子内Rauhut-Currier反应中的首次报道。在两种经典底物的情况下，路易斯钛酸会导致快速的Rauhut-Currier反应。更重要的是，钛和锡路易斯酸是用于更复杂底物的唯一成功试剂，从而说明了路易斯酸试剂有可能促进具有挑战性的分子内Rauhut-Currier反应，而传统试剂无法做到这一点。
• An enantioselective double Diels–Alder approach to the tetracyclic framework of colombiasin A
  作者：Jason H. Chaplin、Alison J. Edwards、Bernard L. Flynn

  DOI：10.1039/b302522e

  日期：——

  The complex tetracyclic carbon skeleton of colombiasin A is conveniently accessed through an enantioselective intermolecular Diels–Alder–sulfoxide elimination–intramolecular Diels–Alder (DA–E–IMDA) sequence.

  哥伦比亚素A的四环碳骨架可通过分子间对映选择性狄尔斯-阿尔德-亚砜消除-分子内狄尔斯-阿尔德（DA-E-IMDA）反应序列轻松构建。