3-(4'-methylphenyl)-2-methyl-3-buten-2-ol | 80516-16-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4'-methylphenyl)-2-methyl-3-buten-2-ol
• 英文别名: 2-methyl-3-p-tolylbut-3-en-2-ol；2-Methyl-3-(4-methylphenyl)but-3-en-2-ol
• CAS: 80516-16-1
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: VMFQDRYGCMBMPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  3-(4'-methylphenyl)-2-methyl-3-buten-2-ol 在 氢氧化钾 、 硫酸 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 30.5h， 生成 1-methyl-4-(2-methyl-1-methyleneallyl)benzene
  参考文献：
  名称：

  Intramolecular Diels-Alder cycloadditions of perchloro(allyloxy)- and perchlorobis(allyloxy)cyclopentadienes

  摘要：

  DOI：

  10.1021/jo00345a038
• 作为产物：
  描述：

  对甲基苯乙酮 在 1,1-二溴乙烷 、 五氯化磷 、 magnesium 作用下， 反应 13.0h， 生成 3-(4'-methylphenyl)-2-methyl-3-buten-2-ol
  参考文献：
  名称：

  Intramolecular Diels-Alder cycloadditions of perchloro(allyloxy)- and perchlorobis(allyloxy)cyclopentadienes

  摘要：

  DOI：

  10.1021/jo00345a038

文献信息

• Chiral ion-pair organocatalyst promotes highly enantioselective 3-exo iodo-cycloetherification of allyl alcohols
  作者：Zhigao Shen、Xixian Pan、Yisheng Lai、Jiadong Hu、Xiaolong Wan、Xiaoge Li、Hui Zhang、Weiqing Xie

  DOI：10.1039/c5sc02485d

  日期：——

  Enantioselective 3-exoiodo-cycloetherification of allyl alcohols was realized by employing a novel ion-pair organocatalyst.

  采用一种新型离子对有机催化剂，实现了烯丙醇的对映选择性3-exo碘环醚化反应。
• Iron-catalyzed boration of allylic alcohols with H₃BO₃ as an additive
  作者：Yuhan Zhou、Huan Wang、Yang Liu、Yilong Zhao、Chunxia Zhang、Jingping Qu

  DOI：10.1080/00397911.2017.1422764

  日期：2018.4.3

  ABSTRACT A method for the synthesis of allylboronates by iron-catalyzed boration of allylic alcohols with H3BO3 as an additive is developed. The introduction of H3BO3 promotes the cleavage of C‒O bond in allylic alcohols obviously. Functional groups, such as fluoro, chloro, bromo, alkyl, and alkoxy, are tolerated well. Thus, various allylboronates are obtained in acceptable yield. GRAPHICAL ABSTRACT

  摘要 开发了一种以 H3BO3 作为添加剂通过铁催化烯丙醇硼化合成烯丙硼酸酯的方法。H3BO3 的引入明显促进了烯丙醇中 C-O 键的断裂。氟、氯、溴、烷基和烷氧基等官能团耐受性良好。因此，以可接受的产率获得了各种烯丙基硼酸酯。图形概要
• A Novel Palladium-Catalyzed Asymmetric Cyclocarbonylation of Allylic Alcohols to γ-Butyrolactones
  作者：Wing-Yiu Yu、Corinne Bensimon、Howard Alper

  DOI：10.1002/chem.19970030313

  日期：——

  AbstractA catalyst system based on [Pd2(dba)3]·CHCl3/(‐)‐BPPM has been found to effect asymmetric cyclocarbonylation of certain prochiral allylic alcohols to produce good yields of optically enriched γ‐butyrolactones. The reaction was performed under an atmosphere of H2 (400 psi) and CO (400 psi) at 100°C in methylene chloride for 48 hours. Asymmetric cyclocarbonylation of allylic alcohols with aliphatic substituents proceeded with moderate enantioselectivities (ee = 25–43%). However, enantiomeric excesses of up to 83% were obtained for substrates containing aromatic substituents, in which case the ee was found to be more sensitive to steric, rather than to electronic factors. Recrystallization of the lactones containing an aromatic group from a mixture of CH2Cl2/Et2O/hexanes (0.5/1.0/8.5), by slow evaporation of the solvent or at low temperature, improved the enantiopurities to >98% ee on a reproducible basis. The asymmetric center of the aromatic lactones was assigned the (S)‐configuration based on the X‐ray crystal structure analysis of enantiopure (S)‐(+)‐3,3‐dimethyl‐2‐(2′‐methylphenyl)‐γ‐butyrolactone (2k). A hydridopalladium intermediate is believed to play a key role in this reaction. Enantioselectivity is thought to be brought about by the preferential formation of 6b. The carbon skeleton of 6b fits into the chiral scaffold of (‐)‐BPPM.
• JUNG, M. E.;LIGHT, L. A., J. ORG. CHEM., 1982, 47, N 6, 1084-1090
  作者：JUNG, M. E.、LIGHT, L. A.

  DOI：——

  日期：——
• CN114874157
  申请人：——

  公开号：——

  公开（公告）日：——