trans-1,3-bis(1-naphthyl)propen-3-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: trans-1,3-bis(1-naphthyl)propen-3-ol
• 英文别名: (E)-1,3-di(naphthalen-1-yl)prop-2-en-1-ol；(E)-1,3-dinaphthalen-1-ylprop-2-en-1-ol
• 化学式: C₂₃H₁₈O
• 分子量: 310.395
• InChiKey: SZBXTLOWWXMCKY-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 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：

  trans-1,3-bis(1-naphthyl)propen-3-ol 在 copper(II) perchlorate hexahydrate 、 叠氮基三甲基硅烷 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 以70%的产率得到(E)-1-(naphthalen-1-yl)-5-(2-(naphthalen-1-yl)vinyl)-1H-tetrazole
  参考文献：
  名称：

  铜催化的仲醇氧化转化为1,5-二取代的四唑

  摘要：

  在催化量的高氯酸铜（II）六水合物[Cu（ClO 4）]存在下，通过使用三甲基叠氮化硅（TMSN 3）作为氮源，发现了中等程度的醇向1,5-二取代的四唑进行温和且方便的氧化转化。2 。6 H 2 O]（5 mol％）和2,3-二氯-5,6-二氰基对苯醌（DDQ）（1.2当量）作为氧化剂。该反应在环境条件下进行，并通过CC键裂解进行。

  DOI：

  10.1002/adsc.201300863
• 作为产物：
  描述：

  1-萘乙酮 在 sodium tetrahydroborate 、 sodium methylate 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 为溶剂， 反应 0.25h， 生成 trans-1,3-bis(1-naphthyl)propen-3-ol
  参考文献：
  名称：

  Chiral recognition and molecular interaction in cellulose derivatives

  摘要：

  Nineteen 1,3-bis(aryl)propane derivatives and six model compounds with a single chromophore were used to explore the chiral discrimination ability of cellulose derivatives, in particular cellulose triphenylcarbamate (CTC), in connection with the mode of interaction of these probe molecules with adsorbents. The interaction was evaluated by conformational analysis of the probe molecules and circular dichroism. Thc 1,3-bis(aryl)propanes with 9-anthryl moieties possessed a highly limited conformation owing to thc bulky substituent and hardly changed their shape on CTC as evidenced by CD spectra; thus, they may be regarded as ''rigid'' substrates. However, these ''rigid'' substrates were resolved quite effectively. On the other hand, those with 2-naphthyl moieties possessed a number of stable conformations and could change their shape in diastereomeric complexes on CTC; thus, they may be assumed as ''soft'' substrates, against which the chiral discrimination was inefficient. The present study revealed that the optical resolution may be interpreted at least partly in terms of the ''rigid'' and ''soft'' concept.

  DOI：

  10.1021/j100193a020

文献信息

• Palladium-Catalyzed Oxidative Cycloisomerization of 2-Cinnamyl-1,3-Dicarbonyls: Synthesis of Functionalized 2-Benzyl Furans
  作者：Rajender Nallagonda、Reddy Rajasekhar Reddy、Prasanta Ghorai

  DOI：10.1002/chem.201502781

  日期：2015.10.12

  A new palladium‐catalyzed intramolecular oxidative cycloisomerization of readily available starting materials, 2‐cinnamyl‐1,3‐dicarbonyls, has been demonstrated for the creation of structurally diverse 2‐benzyl furans. The cycloisomerization occurs by a regioselective 5‐exo‐trig pathway. The reaction shows a broad substrate scope with good to excellent yields. Furthermore, a one‐pot procedure has been

  新型钯催化的分子内氧化环化异构反应可轻松获得，即2-肉桂基-1,3-二羰基原料，可用于形成结构多样的2-苄基呋喃。环异构化是通过区域选择性5 exo- trig途径进行的。该反应显示出广泛的底物范围，具有良好至优异的产率。此外，通过使用现成的肉桂醇和1,3-二酮，可以执行一锅法。
• Synthesis of Densely Substituted α,β,γ,δ-Dienones via the Pd^II-Catalyzed Allylation, H-Migration, and Aerobic Oxidative δ-Hydride Elimination Cascade
  作者：Feng-Quan Yuan、Fu-She Han

  DOI：10.1021/ol203444g

  日期：2012.3.2

  A novel protocol for the highly stereoselective synthesis of E,E-α,β,γ,δ-unsaturated dicarbonyl compounds is presented. Starting from the readily available allylic alcohols and 1,3-diketones, an array of E,E-α,β,γ,δ-dienones can be efficiently synthesized in high yields via Pd-catalyzed dehydrative allylation, H-migration, and aerobic oxidative δ-hydride elimination cascade. In addition to the novel

  提出了一种新的协议，用于E，E- α，β，γ，δ-不饱和二羰基化合物的高度立体选择性合成。从容易获得的烯丙醇和1,3-二酮开始，可以通过Pd催化的脱水烯丙基化，H迁移和好氧反应，以高收率高效地合成一系列E，E- α，β，γ，δ-二烯酮氧化δ-氢化物消除级联反应。除了新颖的反应机理外，还使用1：1的烯丙醇和1,3-二酮作为反应物，使用5 mol％的PdCl 2作为催化剂，使用1 atm的环境友好的O 2作为氧化剂，以及生成仅H 2 O副产物的残留量，使该方案快速，简单，原子效率高且清洁。
• Organocatalytic α-Allylation of α-Branched Aldehydes by Synergistic Catalysis of Brønsted Acids and Amines
  作者：Filip Stanek、Maciej Stodulski

  DOI：10.1002/ejoc.201600725

  日期：2016.10

  Herein, we describe the first, fully organocatalytic Tsuji–Trost-type direct α-allylation of α-branched aldehydes by the combined use of N-triflyl amides and secondary amines. Aliphatic, aromatic aldehydes as well as allyl alcohols are converted into the corresponding α-allylated products in moderate to high yields.

  在此，我们描述了第一个完全有机催化的 Tsuji-Trost 型直接 α-烯丙基化反应，该反应通过结合使用 N-三氟甲基酰胺和仲胺来实现 α-支化醛。脂肪族、芳香族醛以及烯丙醇以中等至高产率转化为相应的 α-烯丙基化产物。
• Chiral Brønsted acid catalyzed enantioselective intermolecular allylic aminations
  作者：Minyang Zhuang、Haifeng Du

  DOI：10.1039/c4ob00526k

  日期：——

  This paper describes an enantioselective intermolecular allylic amination catalyzed by a chiral Brønsted acid via a possible chiral contact ion pair intermediate. A variety of symmetrical or unsymmetrical allylic alcohols can be smoothly aminated to afford the desired products in moderate to high yields with good enantioselectivities and/or regioselectivities.

  本文描述了通过手性布朗斯台德酸通过可能的手性接触离子对中间体催化的对映选择性分子间烯丙基胺化反应。可以将各种对称或不对称的烯丙基醇平滑地胺化，以中等至高收率提供所需的产物，并具有良好的对映选择性和/或区域选择性。
• Copper-Catalyzed Oxidative Transformation of Secondary Alcohols to 1,5-Disubstituted Tetrazoles
  作者：Balaji V. Rokade、Karthik Gadde、Kandikere Ramaiah Prabhu

  DOI：10.1002/adsc.201300863

  日期：2014.3.24

  A mild and convenient oxidative transformation of secondary alcohols to 1,5‐disubstituted tetrazoles is uncovered by employing trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of a catalytic amount of copper(II) perchlorate hexahydrate [Cu(ClO4)2.6 H2O] (5 mol%) and 2,3‐dichloro‐5,6‐dicyano‐para‐benzoquinone (DDQ) (1.2 equiv.) as an oxidant. This reaction is performed under ambient

  在催化量的高氯酸铜（II）六水合物[Cu（ClO 4）]存在下，通过使用三甲基叠氮化硅（TMSN 3）作为氮源，发现了中等程度的醇向1,5-二取代的四唑进行温和且方便的氧化转化。2 。6 H 2 O]（5 mol％）和2,3-二氯-5,6-二氰基对苯醌（DDQ）（1.2当量）作为氧化剂。该反应在环境条件下进行，并通过CC键裂解进行。