(E)-3-(anthracen-9-yl)prop-2-en-1-ol | 172098-27-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (E)-3-(anthracen-9-yl)prop-2-en-1-ol
• 英文别名: 3-(9-anthryl)-(E)-2-propene-1-ol；(E)-3-anthracen-9-ylprop-2-en-1-ol
• CAS: 172098-27-0
• 化学式: C₁₇H₁₄O
• 分子量: 234.298
• InChiKey: YFIDAXCQNQYXQH-BJMVGYQFSA-N

物化性质

• 沸点：
  469.5±14.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  (E)-3-(anthracen-9-yl)prop-2-en-1-ol 在 manganese(IV) oxide 作用下， 以 正己烷 为溶剂， 反应 18.0h， 以80%的产率得到(E)-3-(anthracen-9-yl)acrylaldehyde
  参考文献：
  名称：

  Reddy, Majjigapu Janaki Ram; Kumar, Perepogu Arun; Srinivas, Uppalanchi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2007, vol. 46, # 11, p. 1833 - 1847

  摘要：

  DOI：
• 作为产物：
  描述：

  9-蒽甲醛 在 sodium hydride 、 二异丁基氢化铝 、 红霉素 作用下， 以 甲醇 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (E)-3-(anthracen-9-yl)prop-2-en-1-ol
  参考文献：
  名称：

  Wavelength Dependent Trans to Cis and Quantum Chain Isomerizations of Anthrylethylene Derivatives

  摘要：

  Anthrylethylene derivatives 1-4 were synthesized to study their photoisomerization. Interestingly 1 and 2 displayed wavelength dependent trans to cis photoisomerization, whose origin is due to preferential light absorption and excitation of the trans isomer. Triplet sensitization studies revealed that these anthrylethylenes undergo only cis to trans isomerization and not trans to cis isomerization. UV-vis absorption, fluorescence emission, and fluorescence quantum yields were determined for all anthrylethylenes. Dual fluorescence is observed for 1, 2, and cis-1, indicating two different emissive states. The fluorescence solvatochromism displayed by 1, 2, and cis-1 is a clear indication of the involvement of a charge transfer excited state. The quantum yield of isomerization was determined in various solvents and also as a function of concentration. We report here the first ''quantum chain isomerization'' that originates from a singlet excited state. The rationale put forward for the observed quantum chain isomerization process is the involvement of adiabatic isomerization from the singlet excited state and subsequent energy transfer to a ground state molecule.

  DOI：

  10.1021/jo00129a043

文献信息

• Ligand-Controlled Regiodivergent Silylation of Allylic Alcohols by Ni/Cu Catalysis for the Synthesis of Functionalized Allylsilanes
  作者：Yi Gan、Wei Xu、Yuanhong Liu

  DOI：10.1021/acs.orglett.9b03822

  日期：2019.12.6

  Ni/Cu-catalyzed regiodivergent synthesis of allylsilanes directly from allylic alcohols through modulating the steric and electronic properties of the ligands on the nickel catalyst has been developed. Good yields and excellent selectivity were obtained regardless of whether linear or α-branched allylic alcohols were utilized. Mechanistic studies indicate that an allyloxyboronate species is formed during the

  通过调节镍催化剂上配体的空间和电子性质，直接由烯丙基醇直接进行烯丙基硅烷的Ni / Cu催化区域发散性合成已经得到了发展。无论使用线性还是α-支链的烯丙基醇，均获得了良好的收率和优异的选择性。机理研究表明，在反应过程中形成了烯丙氧基硼酸酯物质，这很可能充当了C（烯丙基）-O键氧化加成反应的活化中间体。
• Fe‐Catalyzed Amidation of Allylic Alcohols by Borrowing Hydrogen Catalysis
  作者：Xiaoyun Wu、Wei Ma、Weijun Tang、Dong Xue、Jianliang Xiao、Chao Wang

  DOI：10.1002/chem.202201829

  日期：2022.10.26

  The amidation of allylic alcohols with chiral tert-butylsulfinamide catalyzed by an Earth-abundant Fe complex via a borrowing hydrogen pathway has been developed. With water as the only by-product, a range of synthetically useful chiral sulfinamide olefin derivatives were obtained under mild reaction conditions with exclusive linear selectivity and retention of enantioselectivity.

  已经开发了由地球丰富的 Fe 配合物通过借氢途径催化的烯丙醇与手性叔丁基亚磺酰胺的酰胺化。以水作为唯一的副产物，在温和的反应条件下获得了一系列合成有用的手性亚磺酰胺烯烃衍生物，具有独特的线性选择性和对映选择性的保留。
• 10.1562/0031-8655(2002)076<0029
  作者：Rao, G. Venugopal、Reddy, M. Janaki Ram、Srinivas、Reddy, Maruthi Janaki Ram、Bushan, K. Mani、Rao, V. Jayathirtha

  DOI：10.1562/0031-8655(2002)076<0029

  日期：——
• Chloranil-Sensitized Photolysis of Benzyltrimethylsilanes. Solvent Effect on the Competition between Carbon-Hydrogen and Carbon-Silicon Bond Cleavage
  作者：Enrico Baciocchi、Tiziana Del Giacco、Fausto Elisei、Marcella Ioele

  DOI：10.1021/jo00129a044

  日期：1995.12

  A steady state and laser flash photolysis study of the chloranil (CA)-sensitized oxidation of benzyltrimethylsilane (BTS) and (4-methoxybenzyl)trimethylsilane (MBTS) in different solvents (benzene, CH2Cl2, and MeCN) has been carried out. In benzene, BTS reacts with (3)CA* to give exclusively alpha-substituted benzyltrimethylsilane, whereas with MBTS the alpha-substituted silane is formed together with benzylic desilylation products. The latter situation also holds in CH2Cl2 for BTS. Only desilylation products are obtained from MBTS in CH2Cl2 and from both BTS and MBTS in MeCN. Higher quantum yields in the reactions with BTS than in those with MBTS have been observed in benzene and CH2Cl2. In MeCN, no significant change in quantum yield has been observed on going from BTS to MBTS. In MeCN with both BTS and MBTS and in CH2Cl2 with MBTS, the laser photolysis experiments have shown evidence for the formation of transients which can be attributed to MBTS(.+) and CA(.-) (MBTS in MeCN and CH2Cl2) and to CA(.-) (BTS in MeCN). This indicates that quenching of (3)CA* has taken place via an electron transfer process. Once formed, both BTS.+ and MBTS(.+) undergo exclusive C-Si bond cleavage. In CH2Cl2, this reaction is promoted by CA(.-), and accordingly, MBTS(.+) decays by a second-order kinetics. In MeCN, MBTS(.+) decays by a first-order kinetics and desilylation is promoted by the solvent itself. The same holds for BTS.+ as the decay reaction of this cation radical in MeCN appears much faster than that of CA(.-). In fact, only the transient assigned to the latter species has been observed in the laser photolysis experiments. A different situation has been found for both MBTS and BTS in benzene and BTS in CH2Cl2, where quenching of (3)CA* occurs via a partial charge transfer (CT) triplet complex. The reversible formation of this complex with MBTS in benzene is clearly indicated by the dependence of the observed rate constant for 3CA* quenching on the substrate concentration, which has allowed the association constant for the complex(ca. 400 M(-1)) to be determined. With BTS in benzene and CH2Cl2, the formation of the CT triplet complex is irreversible and rate determining, and the main evidence in this respect comes from the absence of a sizable deuterium kinetic isotope effect for the 3CA* quenching rate. With BTS in benzene, the CT complex undergoes C-H bond cleavage as the exclusive chemical reaction. With MBTS in benzene and BTS in CH2Cl2, both C-H and C-Si bond cleavages take place, and it is suggested that the cleavage of the latter bond requires more transfer of charge in the complex than the cleavage of the C-H bond. Alternatively, in CH2Cl2, the CT complex might evolve in part to a solvent-separated radical ion pair, exclusively leading to the C-Si bond cleavage products. The above results have also allowed an assessment of the scope of the benzyltrimethylsilane probe to detect electron transfer mechanisms.
• Reddy, Majjigapu Janaki Ram; Kumar, Perepogu Arun; Srinivas, Uppalanchi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2007, vol. 46, # 11, p. 1833 - 1847
  作者：Reddy, Majjigapu Janaki Ram、Kumar, Perepogu Arun、Srinivas, Uppalanchi、Reddy, Vummadi Venkat、Reddy, Maruthi Janaki Ram、Rao, G. Venugopal、Rao, Vaidya Jayathirtha

  DOI：——

  日期：——