1-(萘-1-基)-丁-3-烯-1-醇 | 72551-06-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-(萘-1-基)-丁-3-烯-1-醇
• 英文名称: 1-naphthalen-1-yl-but-3-en-1-ol
• 英文别名: 1-(1-naphthyl)-3-buten-1-ol；1-naphthylbut-3-en-1-ol；1-(1-naphthyl)but-3-en-1-ol；1-naphthalen-1-ylbut-3-en-1-ol
• CAS: 72551-06-5
• 化学式: C₁₄H₁₄O
• 分子量: 198.265
• InChiKey: FFNKLJQFZFTUHS-UHFFFAOYSA-N

物化性质

• 沸点：
  150-151 °C(Press: 5 Torr)
• 密度：
  1.085±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  1-(萘-1-基)-丁-3-烯-1-醇 在 三乙胺 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-4-hydroxy-1-(naphthalen-1-yl)but-2-en-1-one
  参考文献：
  名称：

  路易斯酸催化 [3+3] 环丙烷与 γ-羟基烯酮的环化：获得高度官能化的四氢吡喃

  摘要：

  供体-受体环丙烷与γ-羟基烯酮进行[3+3]-环化反应。Sc(OTf)3被发现是最好的催化剂，在温和的反应条件下以良好的收率获得了2,4,4,5-四取代四氢吡喃产物。该反应的普遍性允许合成带有芳基、烷基和杂芳族基团的四取代四氢吡喃。还使用手性 PyBOX 配体初步研究了该过程的催化不对称变体。

  DOI：

  10.1002/ejoc.201601305
• 作为产物：
  描述：

  1-萘甲醛 在 盐酸 、 水 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 1-(萘-1-基)-丁-3-烯-1-醇
  参考文献：
  名称：

  Mesoporous aluminosilicate-catalyzed allylation of carbonyl compounds and acetals

  摘要：

  A mesoporous aluminosilicate (Al-MCM-41) was found to be an effective heterogeneous catalyst for the reaction of both carbonyl compounds and acetals with allylsilanes to afford the corresponding homoallyl silyl ethers and homoallyl alkyl ethers, respectively. Both the mesoporous structure and the presence of aluminum moiety were indispensable for the high catalytic activity of Al-MCM-41. Moreover, Al-MCM-41 could catalyze the reaction of acetals chemoselectively in the presence of the corresponding carbonyl compounds. The solid acid catalyst Al-MCM-41 could be recovered easily by filtration and could be reused three times without a significant loss of catalytic activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.055

文献信息

• Porous and Robust Lanthanide Metal-Organoboron Frameworks as Water Tolerant Lewis Acid Catalysts
  作者：Yan Liu、Ke Mo、Yong Cui

  DOI：10.1021/ic400598x

  日期：2013.9.16

  number of isolated Lewis acid B(III) and Ln(III) sites on the pore surfaces. The Nd-MOF assisted with sodium dodecylsulfate was found to be highly effective, recyclable, and reusable heterogeneous catalyst for the carbonyl allylation reaction, the Diels–Alder reaction, and the Strecker-type reaction in water. The transformations were cocatalyzed by Nd(III) and B(III) Lewis acids, with activities much

  多孔且坚固的12连接金属-有机骨架（MOF）是通过将四核镧系（Ln）碳酸酯簇与有机硼衍生的三羧酸酯桥联配体连接而构建的。高连接性的Ln-MOF具有出色的热稳定性和水解稳定性，并且在孔表面具有大量的孤立的路易斯酸B（III）和Ln（III）位。发现Nd-MOF辅以十二烷基硫酸钠可用于水中的羰基烯丙基化反应，Diels-Alder反应和Strecker型反应，是高效，可回收和可重复使用的非均相催化剂。Nd（III）和B（III）Lewis酸可共同催化转化，其活性远高于有机硼和镧系元素对应物及其混合物的活性。
• An electrochemical tandem reaction: one-pot synthesis of homoallylic alcohols from alcohols in aqueous media
  作者：Li Zhang、Zhenggen Zha、Zhenlei Zhang、Yunfeng Li、Zhiyong Wang

  DOI：10.1039/c0cc01964j

  日期：——

  A tandem electrosynthesis of homoallylic alcohols from alcohols in one-pot was realized. In virtue of this one-pot electrosynthesis, the traditional reaction substrates of allylation were broadened from carbonyl compounds to alcohols.

  实现了一锅法从醇类串联合成均烯丙基醇。通过这种一锅电合成，将烯丙基化的传统反应底物从羰基化合物扩展为醇。
• Stereoselective Synthesis of Cyclic Guanidines by Directed Diamination of Unactivated Alkenes
  作者：Artur K. Mailyan、Kyle Young、Joanna L. Chen、Bradley T. Reid、Armen Zakarian

  DOI：10.1021/acs.orglett.6b02778

  日期：2016.11.4

  method for a directed stereoselective guanidinylation of alkenes is described. The guanidine unit can be delivered as an intact fragment by a hydroxy or carboxy group, usually with a high level of stereocontrol. After the guanidine delivery, the directing group can be cleaved under exceptionally mild conditions, typically by alcoholysis in the presence of acetic acid. Broad functional group tolerance

  描述了用于烯烃的定向立体选择性胍基化的方法。胍单元可以通过羟基或羧基作为完整片段递送，通常具有高水平的立体控制。胍基递送后，可以在异常温和的条件下，通常通过在乙酸的存在下进行醇解，来切割该导向基团。宽泛的官能团耐受性和环胍基化的温和反应条件表明其在药物化学和天然产物合成中的应用。
• Silver Oxide as a Novel Catalyst for Carbon–Carbon Bond-forming Reactions in Aqueous Media
  作者：Masaharu Ueno、Arata Tanoue、Shu Kobayashi

  DOI：10.1246/cl.2010.652

  日期：2010.6.5

  Silver oxide was found to be an excellent catalyst for allylation reactions of allyltributyltins with aldehydes in aqueous media. Despite the very low solubility of silver oxide in the media, the reactions proceeded smoothly, and the catalyst was recovered and reused. When α-methyl-substituted allyltributyltin was used as the nucleophile, the corresponding α-adducts were obtained exclusively in high yields with good anti-selectivity. A reaction mechanism including transmetalation from tin to silver is proposed.

  银氧化物在烯丙基三丁锡与醛在水相中的烯丙基化反应中表现出优异的催化性能。尽管银氧化物在介质中的溶解度极低，反应仍顺利进行，且催化剂可回收并重复使用。当使用α-甲基取代的烯丙基三丁锡作为亲核试剂时，以高产率且具有良好反式选择性地获得了相应的α-加成产物。提出了一种包含从锡到银的转金属化步骤的反应机理。
• Rhenium complex-catalyzed allylation of aldehydes with allyltributylstannane
  作者：Yutaka Nishiyama、Fujio Kakushou、Noboru Sonoda

  DOI：10.1016/j.tetlet.2004.12.022

  日期：2005.1

  was confirmed that the rhenium complex, ReBr(CO)5, catalyzed the allylation of aldehydes with allyltributylstannane to give the corresponding homoallylic alcohols in moderate to good yields. Similarly, the reaction of aldehydes with enol silyl ether was efficiently promoted by the rhenium catalyst to afford the corresponding β-hydroxy carbonyl compounds.

  证实that络合物ReBr（CO）5催化醛与烯丙基三丁基锡烷的烯丙基化，以中等至良好的产率得到相应的均烯丙基醇。类似地，by催化剂有效地促进了醛与烯醇甲硅烷基醚的反应，得到了相应的β-羟基羰基化合物。