3-(4-甲氧基苯基)-1-苯基-2-丙烯-1-醇 | 3906-07-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 3-(4-甲氧基苯基)-1-苯基-2-丙烯-1-醇
• 英文名称: (E)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-ol
• 英文别名: (R)-(E)-3-(4-methoxylphenyl)-1-phenyl-2-propen-1-ol；(R,E)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-ol；(R,E)-3-(p-methoxyphenyl)-1-phenylprop-2-en-1-ol；(E,1R)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-ol
• CAS: 3906-07-8
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: CLHFQGXGDCYRMY-ONOODXEBSA-N

物化性质

• 沸点：
  413.9±40.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (E)-3-(4-甲氧基苯基)-1-苯基-丙-2-烯-1-酮 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 lithium hydroxide monohydrate 、 氢气 、 (4S,4'S)-2,2'-bis(o-diphenylphosphinophenyl)-4,4',5,5'-tetrahydro-4,4'-bi(1,3-oxazole) 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、1.0 MPa 条件下， 反应 6.0h， 以93%的产率得到3-(4-甲氧基苯基)-1-苯基-2-丙烯-1-醇
  参考文献：
  名称：

  用于α，β-不饱和酮不对称加氢成烯丙醇的稳健的Ru-PNNP催化剂体系

  摘要：

  发现了一种鲁棒且稳定的Ru-Biphosphinobioxazoline催化剂体系，可将烯酮高度对映选择性地氢化为烯丙醇。一系列无环α，β-不饱和酮反应良好，以高收率（高达98％）和对映选择性（高达98％ee）提供所需的产物。简单的操作过程以及对水和空气的耐受性使这种催化更加实用和吸引人。

  DOI：

  10.1016/j.tetlet.2013.10.051

文献信息

• Enantioselective Reduction of Ketones Catalyzed by Rare-Earth Metals Complexed with Phenoxy Modified Chiral Prolinols
  作者：Peng Song、Chengrong Lu、Zenghui Fei、Bei Zhao、Yingming Yao

  DOI：10.1021/acs.joc.8b00783

  日期：2018.6.1

  Enantioselective reduction of ketones and α,β-unsaturated ketones by pinacolborane (HBpin) has been well-established by using chiral rare-earth metal catalysts with phenoxy modified prolinols. A number of highly optically active alcohols were obtained from reduction of simple ketones catalyzed by ytterbium complex 1 [L4Yb(L4H)] (H2L4 = (S)-2- tert-butyl-6-((2-(hydroxydiphenylmethyl)pyrrolidin-1-yl)methyl)phenol)

  频哪醇硼烷（HBpin）对酮和α，β-不饱和酮的对映选择性还原已通过使用手性稀土金属催化剂与苯氧基改性的脯氨醇进行了很好的建立。reduction配合物1 [L 4 Yb（L 4 H）]（H 2 L 4 =（S）-2-叔丁基-6-（（2 -（羟基二苯基甲基）吡咯烷-1-基）甲基）苯酚）。此外，α，β-不饱和酮被单组分手性y配合物催化，具有良好的收率，高对映选择性和完全化学选择性，可选择性地还原成多种手性烯丙基醇。2 [L 1 Yb（L 1 H）]（H 2 L 1 =（S）-2,4-二叔丁基-6-（（（2-（羟基二苯甲基）吡咯烷基-1-基）甲基）苯酚） 。
• Asymmetric additive-free aryl addition to aldehydes using perhydrobenzoxazines as ligands and boroxins as aryl source
  作者：Rebeca Infante、Javier Nieto、Celia Andrés

  DOI：10.1039/c1ob05717k

  日期：——

  A highly efficient enantioselective aryl addition to aldehydes using boroxins as aryl source and conformationally restricted perhydro-1,3-benzoxazines as ligands is reported. Both enantiomeric forms of chiral arylphenylmethanols and 1,1′-disubstituted diarylmethanols are afforded with excellent yields and enantioselectivities using the same ligand by means of an appropriate combination of boroxin and aromatic aldehyde. The enantiocontrol is not significantly influenced by electronic effects or steric hindrance, even with substituted boroxins. Very homogeneous ee's are reached when substituted arylboroxins are employed, without the use of any class of additive or pre-treatment.

  报道了一种高效的对映选择性芳基加成反应，利用硼氧烷作为芳基来源，并采用构象限制的过氢-1,3-苯并呋喃作为配体。通过合理组合硼氧烷和芳香醛，使用相同的配体可以获得手性芳基苯甲醇和1,1′-二取代二芳基甲醇的两种对映体，具有优异的产率和对映选择性。即使在有取代的硼氧烷存在时，对映控制也不受电子效应或空间位阻的显著影响。当使用取代芳基硼氧烷时，可以达到非常均匀的对映体过量，并且无需任何类型的添加剂或预处理。
• Ru(II)-Catalyzed Asymmetric Transfer Hydrogenation of Chalcones in Water: Application to the Enantioselective Synthesis of Flavans BW683C and Tephrowatsin E
  作者：Felipe C. Demidoff、Guilherme S. Caleffi、Marcella Figueiredo、Paulo R. R. Costa

  DOI：10.1021/acs.joc.2c01733

  日期：2022.11.4

  The stereoelectronic effects of electron-donating and electron-withdrawing groups at the ortho, meta and para positions of both aromatic rings were evaluated. The 2-OH group at the B ring was well tolerated, allowing a straightforward enantioselective synthesis of two flavans through the Mitsunobu cyclization, the antiviral (S)-BW683C and the natural flavan (S)-tephrowatsin E.

  oxo-tethered-Ru(II) 预催化剂通过不对称转移氢化促进以甲酸钠为氢源的查耳酮的一锅法 C=C/C=O 还原。获得了 27 种 1,3-二芳基丙-1-醇，收率（高达 96%）和对映体纯度（高达 98:2）。我们的数据表明，烯酮首先被还原为相应的二氢查尔酮（1,4-选择性），然后还原为 1,3-二芳基丙-1-醇（C=O 还原）。邻位、间位和对位给电子和吸电子基团的立体电子效应评估了两个芳环的位置。B 环上的 2-OH 基团具有良好的耐受性，允许通过 Mitsunobu 环化直接对映选择性合成两种黄烷，即抗病毒 ( S )-BW683C 和天然黄烷 ( S )-tephrowatsin E。
• 10.1002/anie.202405290
  作者：Lin, Chuiyi、Zhang, Jiwu、Sun, Zhao、Guo, Yinlong、Chong, Qinglei、Zhang, Zhihan、Meng, Fanke

  DOI：10.1002/anie.202405290

  日期：——

  A new approach for highly efficient and enantioselective alkenylation of aldehydes promoted by an easily accessible cobalt-based complex was developed. This protocol represents the first example of incorporating a wide range of alkenyl groups with diversified substitution patterns as well as axial stereogenicity into enantioenriched allylic alcohols.

  开发了一种由易于获得的钴基络合物促进的醛的高效和对映选择性烯基化的新方法。该方案代表了将具有多样化取代模式以及轴向立体异构性的各种烯基纳入对映体富集的烯丙醇中的第一个例子。
• Enantiospecific, Nickel-Catalyzed Cross-Couplings of Allylic Pivalates and Arylboroxines
  作者：Harathi D. Srinivas、Qi Zhou、Mary P. Watson

  DOI：10.1021/ol5016724

  日期：2014.7.3

  We have developed an enantiospecific, nickel-catalyzed cross-coupling of unsymmetric 1,3-disubstituted allylic pivalates with arylboroxines. The success of this reaction relies on the use of BnPPh2 as a supporting ligand for the nickel(0) catalyst and NaOMe as a base. This method shows excellent functional group tolerance and broad scope in both the allylic pivalate and arylboroxine, enabling the preparation of 1,3-diaryl allylic products in high yields with excellent levels of regioselectivity and stereochemical fidelity.