(E,E)-4-methyl-6-phenyl-3,5-hexadiene-2-one | 29179-16-6

• 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,E)-4-methyl-6-phenyl-3,5-hexadiene-2-one
• 英文别名: ethyl (2E, 4E)-3-methyl-5-phenylpenta-2,4-dienoate；(3E,5E)-4-methyl-6-phenylhexa-3,5-dien-2-one
• CAS: 29179-16-6
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: XGTSSANFIZJPCN-BNFZFUHLSA-N

物化性质

• 沸点：
  328.5±21.0 °C(Predicted)
• 密度：
  0.996±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E,E)-4-methyl-6-phenyl-3,5-hexadiene-2-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以85%的产率得到(3E,5E)-4-Methyl-6-phenyl-hexa-3,5-dien-2-ol
  参考文献：
  名称：

  Highly Like-Selective [4 + 2] Cycloadditions of Chiral Dienols: The Importance of 1,3-Allylic Strain in the Hydroxy-Directed Stereocontrol

  摘要：

  The chiral open-chain dienols 3a,b, which possess 1,3-allylic strain due to the presence of a cis substituent, give with the dienophiles maleic anhydride (MA), N-phenyl maleimide (NPM), 4-phenyl- (PTAD), and 4-methyl-1,2,4-triazoline-3,5-dione (MTAD) the corresponding [4 + 2] cycloadducts in very good yields and with high like selectivity. In contrast to previous reports on dienols without 1,3-allylic strain, the sense of diastereoselectivity does not vary with the dienophile type. The cis substituent aligns preferred conformations in the ground and transition states for which the hydrogen atom is placed in the sterically most biased inside position. Sterically and electronically controlled dienophile attack on these rotamers leads to the observed like stereochemistry. The participation of electronic features, most prominently hydroxy-directed stereocontrol, is substantiated by solvent effects in the triazolinedione cycloadditions, i.e., lower pi-facial selectivities are observed in polar solvents. The present results demonstrate the efficacy of 1,3-allylic strain in promoting conformational preferences in [4 + 2] cycloadditions with asymmetric dienols.

  DOI：

  10.1021/ja00141a010
• 作为产物：
  描述：

  (2Z,4E)-3-methyl-5-phenylpenta-2,4-dienoic acid 在 碘 作用下， 以 乙醚 、 苯 为溶剂， 生成 (E,E)-4-methyl-6-phenyl-3,5-hexadiene-2-one
  参考文献：
  名称：

  Photoisomerization products of conjugated dienones

  摘要：

  DOI：

  10.1021/jo00813a030

文献信息

• Heterogeneous versus Homogeneous Copper(II) Catalysis in Enantioselective Conjugate-Addition Reactions of Boron in Water
  作者：Taku Kitanosono、Pengyu Xu、Shū Kobayashi

  DOI：10.1002/asia.201300997

  日期：2014.1

  reported for the conjugate addition of boron. Heterogeneous cat. 1 also gave high yields and enantioselectivities with some substrates and also gave the highest TOF (43 200 h−1) for an asymmetric conjugate‐addition reaction of boron. In addition, the catalyst systems were also applicable to the conjugate addition of boron to α,β,γ,δ‐unsaturated carbonyl compounds, although such reactions have previously

  我们已经开发了Cu II催化的硼在水中与α，β-不饱和羰基化合物和α，β，γ，δ-不饱和羰基化合物的对映体共轭加成反应。与先前报道的需要有机溶剂的Cu I催化相反，发现手性Cu II催化在水中有效地进行。已经开发了三种催化剂体系：催化剂。1：具有手性配体L 1的Cu（OH）2；猫。2：具有配体L1的Cu（OH）2和乙酸；和猫。3：具有配体L1的Cu（OAc）2。而猫。1是异构系统，猫。2和猫。3是同质系统。我们测试了27种α，β-不饱和羰基化合物和α，β-不饱和腈化合物，包括无环和环状α，β-不饱和酮，无环和环状β，β-二取代的烯酮，无环和环状α，β-不饱和酯（包括其β，β-二取代形式）和无环α，β-不饱和酰胺（包括其β，β-二取代形式）。我们找到那只猫。2和猫。图3显示了几乎所有底物的高产率和对映选择性。值得注意的是，没有报道过能以高收率和高对映选择性耐受所有这些底物的催化剂。异类猫。1
• Regiocontrolled Ruthenium-Catalyzed Isomerization of Propargyl Alcohols
  作者：Edgar Haak、Steffen Skowaisa

  DOI：10.1055/a-2288-3074

  日期：2024.11

  ruthenium complex allows control of regioselectivity in the ruthenium-catalyzed isomerization of propargyl alcohols through the choice of additive. Thereby, both products of the Meyer–Schuster rearrangement and redox isomerization products are selectively accessible. In the presence of hydroxylamine-O-sulfonic acid, unsaturated nitriles are formed instead. The ruthenium catalyst is readily available and

  二氨基环戊二烯酮钌络合物可以通过选择添加剂来控制钌催化的炔丙醇异构化的区域选择性。因此，Meyer-Schuster 重排产物和氧化还原异构化产物都可以选择性地获得。在羟胺-O-磺酸存在下，反而形成不饱和腈。钌催化剂易于获得，并且对水分、空气和酸性条件稳定。
• ANDERSON, P. N.;ARGO, C. B.;SHARP, J. T., J. CHEM. SOC. PERKIN TRANS., 1981, N 11, 2761-2763
  作者：ANDERSON, P. N.、ARGO, C. B.、SHARP, J. T.

  DOI：——

  日期：——
• BALABAN T. -S.; BALABAN A. T., TETRAHEDRON LETT., 28,(1987) N 12, 1341-1344
  作者：BALABAN T. -S.、 BALABAN A. T.

  DOI：——

  日期：——