4-甲基-1,1-二苯基戊-3-烯-1-醇 | 69492-31-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-甲基-1,1-二苯基戊-3-烯-1-醇
• 英文名称: 4-methyl-1,1-diphenylpent-3-en-1-ol
• CAS: 69492-31-5
• 化学式: C₁₈H₂₀O
• 分子量: 252.356
• InChiKey: OEEBDJWNOMFJNC-UHFFFAOYSA-N

物化性质

• 沸点：
  392.3±11.0 °C(Predicted)
• 密度：
  1.037±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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-甲基-1,1-二苯基戊-3-烯-1-醇 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 、 三苯基瞵硫 作用下， 以 二氯甲烷 为溶剂， 以67 %的产率得到3-bromo-2,2-dimethyl-5,5-diphenyltetrahydrofuran
  参考文献：
  名称：

  二烯和酮的双催化分子间还原偶联**

  摘要：

  报道了一种温和的催化方法，用于原料二烯和苯乙烯与酮和亚胺的分子间还原偶联。这种简单方法的应用包括药物分子的有效合成和位点选择性后期功能化。

  DOI：

  10.1002/anie.202314870
• 作为产物：
  描述：

  1-溴-3-甲基-2-丁烯 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 4-甲基-1,1-二苯基戊-3-烯-1-醇
  参考文献：
  名称：

  α-Regioselective construction of gem-bisprenyl structures via zinc-mediated prenylation of esters in THF

  摘要：

  The in situ generated prenylzinc reagent from the reaction of zinc with prenyl bromide has been shown to undergo a new type of alpha-regioselective addition reaction with a wide range of esters that affords gem-bisprenyl structures. The reaction proceeds under mild conditions to provide alpha,alpha'-adducts with complete alpha-regioselectivity. A mechanism with the consideration of the steric factors is proposed to account for the regioselective results. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.008

文献信息

• Highly α-regioselective neodymium-mediated allylation of diaryl ketones
  作者：Fang Zhang、Ru Wang、San Wu、Peipei Wang、Songlin Zhang

  DOI：10.1039/c6ra18378f

  日期：——

  The first utility of neodymium as a mediating-metal in the highly [small alpha]-regioselective Barbier reaction of diaryl ketones with allyl halides was reported in this paper. This reaction was conveniently carried...

  本文报道了钕在二芳基酮与烯丙基卤化物的高度[小]-区域选择性Barbier反应中作为介导金属的第一个用途。该反应方便地进行。
• α-Regioselective Barbier Reaction of Carbonyl Compounds and Allyl Halides Mediated by Praseodymium
  作者：San Wu、Ying Li、Songlin Zhang

  DOI：10.1021/acs.joc.6b01466

  日期：2016.9.2

  first utility of praseodymium as a mediating metal in the Barbier reaction of carbonyl compounds with allyl halides was reported in this paper. In contrast to the traditional metal-mediated or catalyzed Barbier reactions, exclusive α-adducts were obtained in this one-pot reaction with a broad scope of substrates and feasible reaction conditions.

  本文报道了ase在羰基化合物与烯丙基卤化物的Barbier反应中作为中介金属的第一个用途。与传统的金属介导的或催化的Barbier反应相反，在这种一锅法反应中获得了专有的α-加合物，具有广泛的底物范围和可行的反应条件。
• Catalytic Enantioselective Epoxidation of Tertiary Allylic and Homoallylic Alcohols
  作者：José Luis Olivares-Romero、Zhi Li、Hisashi Yamamoto

  DOI：10.1021/ja401182a

  日期：2013.3.6

  for the enantioselective epoxidation of both tertiary allylic and homoallylic alcohols catalyzed by Hf(IV)-bishydroxamic acid (BHA) complexes is described. Asymmetric epoxidation, kinetic resolution, and desymmetrization have been developed, demonstrating the flexible nature of the Hf(IV)-BHA system. This is the first report in which these substrates were obtained with enantioselectivities of up to

  描述了一种由 Hf (IV)-双异羟肟酸 (BHA) 配合物催化的叔烯丙醇和高烯丙醇的对映选择性环氧化的有效且通用的方法。不对称环氧化、动力学拆分和去对称化已经得到发展，证明了 Hf(IV)-BHA 系统的灵活性。这是获得这些底物的对映选择性高达 99% 的第一份报告。
• Photocatalytic Barbier reaction – visible-light induced allylation and benzylation of aldehydes and ketones
  作者：Anna Lucia Berger、Karsten Donabauer、Burkhard König

  DOI：10.1039/c8sc02038h

  日期：——

  We report a photocatalytic version of the Barbier type reaction using readily available allyl or benzyl bromides and aromatic aldehydes or ketones as starting materials to generate allylic or benzylic alcohols. The reaction proceeds at room temperature under visible light irradiation with the organic dye 3,7-di(4-biphenyl)1-naphthalene-10-phenoxazine as a photocatalyst and DIPEA as sacrificial electron

  我们报道了巴比尔型反应的光催化版本，使用容易获得的烯丙基或苄基溴和芳香醛或酮作为起始材料来生成烯丙醇或苄醇。该反应在室温可见光照射下进行，有机染料3,7-二(4-联苯)1-萘-10-吩恶嗪作为光催化剂，DIPEA作为牺牲电子供体。所提出的羰基和烯丙基或苄基的交叉偶联机制得到了光谱研究和循环伏安法测量的支持。
• Photoinduced Allylation of Aromatic Carbonyl Compounds by Allylic Stannanes
  作者：Akio Takuwa、Hiroyuki Tagawa、Hidetoshi Iwamoto、Osamu Soga、Kazuhiro Maruyama

  DOI：10.1246/cl.1987.1091

  日期：1987.6.5

  Irradiation of aromatic carbonyl compounds and allyl-, 2-methyl-2-propenyl-, or 3-methyl-2-butenyltrimethylstannanes in acetonitrile afforded δ,γ-unsaturated alcohols as major product. A photoinduced electron transfer mechanism is proposed for the allylations.

  芳族羰基化合物和烯丙基-、2-甲基-2-丙烯基-或3-甲基-2-丁烯基三甲基锡烷在乙腈中的辐照得到δ，γ-不饱和醇作为主要产物。提出了烯丙基化的光致电子转移机制。