(E)-1,5-diphenylpent-3-en-1-ol

• 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: (E)-1,5-diphenylpent-3-en-1-ol
• 化学式: C₁₇H₁₈O
• 分子量: 238.329
• InChiKey: QYIWEIZVOKWTEG-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-methoxybenzyl 1H-imidazole-1-carboxylate 、 (E)-1,5-diphenylpent-3-en-1-ol 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以85 %的产率得到(E)-1,5-diphenylpent-3-en-1-yl (4-methoxybenzyl) carbonate
  参考文献：
  名称：

  Synthesis of 1,3‐Dioxan‐2‐ones by Photo‐Aerobic Selenium‐π‐Acid Multicatalysis

  摘要：

  AbstractAn expedient method for the synthesis of cyclic carbonates from homoallylic carbonic acid esters by means of photo‐aerobic selenium‐π‐acid multicatalysis is reported. Until now, conceptually related methods commonly relied either on the stoichiometric addition of electrophiles onto the substrate's alkene moiety or the presence of pre‐installed leaving groups in allylic position of said alkene to – in part, catalytically – initiate an intramolecular attack by an adjacent carbonic acid ester group. In sharp contrast, the current study shows that the C−C double bond of homoallylic carbonic acid esters can be directly activated by the catalytic interplay of a pyrylium dye and a diselane using ambient air as the sole oxidant and visible light as an energy source.

  DOI：

  10.1002/ejoc.202201180
• 作为产物：
  描述：

  (E)-1,5-diphenylpent-3-en-1-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以82 %的产率得到(E)-1,5-diphenylpent-3-en-1-ol
  参考文献：
  名称：

  Synthesis of 1,3‐Dioxan‐2‐ones by Photo‐Aerobic Selenium‐π‐Acid Multicatalysis

  摘要：

  AbstractAn expedient method for the synthesis of cyclic carbonates from homoallylic carbonic acid esters by means of photo‐aerobic selenium‐π‐acid multicatalysis is reported. Until now, conceptually related methods commonly relied either on the stoichiometric addition of electrophiles onto the substrate's alkene moiety or the presence of pre‐installed leaving groups in allylic position of said alkene to – in part, catalytically – initiate an intramolecular attack by an adjacent carbonic acid ester group. In sharp contrast, the current study shows that the C−C double bond of homoallylic carbonic acid esters can be directly activated by the catalytic interplay of a pyrylium dye and a diselane using ambient air as the sole oxidant and visible light as an energy source.

  DOI：

  10.1002/ejoc.202201180

文献信息

• Regio- and <i>Trans</i>-Selective Ni-Catalyzed Coupling of Butadiene, Carbonyls, and Arylboronic Acids to Homoallylic Alcohols under Base-Free Conditions
  作者：Yu-Qing Li、Guang Chen、Shi-Liang Shi

  DOI：10.1021/acs.orglett.1c00488

  日期：2021.4.2

  We herein report a Ni-catalyzed three-component coupling of 1,3-butadiene, carbonyl compounds, and arylboronic acids as a general synthetic approach to 1,4-disubstituted homoallylic alcohols, an important class of compounds, which have previously not been straightforward to access. The reaction occurs efficiently using a Ni(cod)2 catalyst without any external base and ligand at ambient temperature

  我们在本文中报道了Ni催化的1,3-丁二烯，羰基化合物和芳基硼​​酸的三组分偶联，作为1,4-二取代的均丙醇的重要合成方法，这是一类重要的化合物，以前并不简单访问。使用Ni（cod）2催化剂可在环境温度下有效地进行反应，而无需使用任何外部碱和配体，并且可在一次操作中对原料丁二烯进行高度区域选择性和反选择性的1,4-二叉官能化。这个简单而实用的协议可以应用于广泛范围的基材。中性条件显示了对高度碱敏感的官能团的非凡耐受性。
• A Mild Oxidative Aryl Radical Addition into Alkenes by Aerobic Oxidation of Arylhydrazines
  作者：Tsuyoshi Taniguchi、Hisaaki Zaimoku、Hiroyuki Ishibashi

  DOI：10.1002/chem.201003060

  日期：2011.4.4

  A mild and practical oxyarylation of alkenes by oxidative radical addition has been developed by using aerobic oxidation of hydrazine compounds. The use of a catalytic amount of potassium ferrocyanide trihydrate (K4[Fe(CN)6]⋅3 H2O) and water accelerated this radical reaction to give peroxides or alcohols from simple alkenes in good yields. The environmentally friendly and economical radical reactions

  通过使用肼化合物的需氧氧化，已经开发了通过氧化自由基加成的烯烃的温和而实用的氧化芳基化反应。催化量的三水合亚铁氰化钾（K 4 [Fe（CN）6 ]⋅3H 2 O）和水的使用加速了这种自由基反应，从而以良好的收率从简单的烯烃制得过氧化物或醇。在室温下，在铁催化剂，氧气和水的存在下，实现了环保，经济的自由基反应。还描述了一种涉及苯胺作为自由基前体的方法。
• Nickel-catalysed three-component connection reaction of a phenyl group, conjugated dienes, and aldehydes: stereoselective synthesis of (E)-5-phenyl-3-penten-1-ols and (E)-3-methyl-5-phenyl-3-penten-1-ols
  作者：Kazufumi Shibata、Masanari Kimura、Keisuke Kojima、Shuji Tanaka、Yoshinao Tamaru

  DOI：10.1016/s0022-328x(00)00890-1

  日期：2001.4

  presence of 10 mol% of Ni(acac)2, Ph2Zn reacts with 1,3-butadiene and aldehydes at room temperature to give 1-alkyl and 1-aryl substituted (E)-5-phenyl-3-penten-1-ols (3) in good yields. Under similar conditions, the three components of Ph3BZnEt2, isoprene, and aldehydes combine with each other to furnish 1-alkyl and 1-aryl substituted (E)-3-methyl-5-phenyl-3-penten-1-ols (5) in good yields.

  在10摩尔％的Ni（acac）2存在下，Ph 2 Zn在室温下与1,3-丁二烯和醛反应，生成1-烷基和1-芳基取代的（E）-5-苯基-3-戊烯-1-醇（3），收率高。在相似的条件下，Ph 3 BZnEt 2的三种成分，异戊二烯和醛相互结合，生成1-烷基和1-芳基取代的（E）-3-甲基-5-苯基-3-戊烯-1-醇（5）丰产。
• Nickel(0)-Catalyzed Three-Component Connection Reaction of Dimethylzinc, 1,3-Dienes, and Carbonyl Compounds
  作者：Masanari Kimura、Shintaro Matsuo、Kazufumi Shibata、Yoshinao Tamaru

  DOI：10.1002/(sici)1521-3773(19991115)38:22<3386::aid-anie3386>3.0.co;2-w

  日期：1999.11.15

  Linear 1:1:1 coupling of dimethylzinc, 1,3-dienes, and carbonyl compounds in this order is facilitated by catalytic amounts of [Ni(acac)(2)] to give (E)-3-hexen-1-ols in good yields under mild conditions [Eq. (a)]. Increasing steric hindrance at the carbonyl group favors formation of the 1:2:1 adduct, and this is the sole product when the carbonyl compound is acetone. acac=acetylacetonate.

  催化量的[Ni（acac）（2）]促进了二甲基锌，1,3-二烯和羰基化合物的线性1：1：1偶联，生成（E）-3-hexen-1-ols在温和条件下的收率很高[等式 （一种）]。在羰基上增加位阻有利于形成1：2：1加合物，当羰基化合物为丙酮时，这是唯一的产物。acac ＝乙酰丙酮酸酯。
• Nickel-Catalyzed Three-Component Cross-Electrophile Coupling of 1,3-Dienes with Aldehydes and Aryl Bromides
  作者：Ya-Qiong Qi、Shuai Liu、Yan Xu、Yang Li、Tong Su、Hai-Liang Ni、Yuanji Gao、Wenhao Yu、Peng Cao、Ping Hu、Ke-Qing Zhao、Bi-Qin Wang、Bin Chen

  DOI：10.1021/acs.orglett.2c01648

  日期：2022.7.22

  We herein report a Ni-catalyzed three-component cross-electrophile coupling of 1,3-dienes with aldehydes and aryl bromides using manganese metal as the reducing agent. This efficient protocol accomplishes dicarbofunctionalization of 1,3-dienes to synthesize diverse structural 1,4-disubstituted homoallylic alcohols by forming two new C–C bonds in one time. Mechanistic study suggests that an allyl-nickel(I)

  我们在此报道了使用锰金属作为还原剂的 1,3-二烯与醛和芳基溴化物的 Ni 催化的三组分交叉亲电偶联。这种有效的方案通过一次形成两个新的 C-C 键来完成 1,3-二烯的二碳官能化，从而合成不同结构的 1,4-二取代高烯丙醇。机理研究表明，烯丙基镍 (I) 物种参与了催化循环。