4-甲基-6-叔丁基香豆素 | 17874-32-7

• 物质功能分类: 医药中间体 - 吡喃类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 4-甲基-6-叔丁基香豆素
• 英文名称: 4-methyl-6-tert-butylcoumarin
• 英文别名: 6-tert-butyl-4-methylcoumarin；6-tert-butyl-4-methyl-chromen-2-one；6-tert-butyl-4-methyl-coumarin；6-tert-Butyl-4-methyl-cumarin；6-(tert-butyl)-4-methyl-2H-2-chromenone；6-tert-butyl-4-methylchromen-2-one
• CAS: 17874-32-7
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: BVQZHRREUVIRFZ-UHFFFAOYSA-N

物化性质

• 熔点：
  123 °C
• 沸点：
  336.1±31.0 °C(Predicted)
• 密度：
  1.071±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 安全说明：
  S24/25,S36/37
• 危险类别码：
  R20/21/22
• 海关编码：
  2932209090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302+H312+H332,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  4-甲基-6-叔丁基香豆素 在 palladium-carbon 作用下， 以 乙醇 、 氢气 为溶剂， 生成 6-(tert-Butyl)-4-methyl-2-chromanone
  参考文献：
  名称：

  Novel fragrance compound

  摘要：

  2-色酮（2-chromanones）在4位置换有三个烷基基团，其总碳数在14到18范围内的新化合物具有麝香气味特性，可用于香水和带香产品中。4,6,8-三烷基取代模式特别受欢迎。

  公开号：

  EP1036792A1
• 作为产物：
  描述：

  4-tert-butylphenyl 3-oxobutanoate 在 硫酸 作用下， 反应 24.0h， 以48%的产率得到4-甲基-6-叔丁基香豆素
  参考文献：
  名称：

  Preparation of Newtert-Butyl Substituted Coumarins, Thiocoumarins and Dithiocoumarins

  摘要：

  6-tert-Butyl-4-methyl- and 6,8-di-tert-butyl-4-methylcoumarin were prepared from tert-butylphenols and diketene via the corresponding aryl acetoacetates. 6-tertButyl-4-methyl-thiocoumarin (6) was obtained from 6-tert-butylthiophenol. Thionation with LAWESSON's or DAVY's reagent led to the related thion- and dithiocoumarins. The structures were proved by NMR spectroscopy and an X-ray structure analysis of 6.

  DOI：

  10.1080/10426500701340949

文献信息

• 10A-AZALIDE COMPOUND CROSSLINKED AT 10A- AND 12-POSITIONS
  申请人：Sugimoto Tomohiro

  公开号：US20110237784A1

  公开（公告）日：2011-09-29

  A novel 10a-azalide compound crosslinked at the 10a- and 12-positions, which is represented by the following formula, and is effective on even Hemophilus influenzae , or erythromycin resistant bacteria (e.g., resistant pneumococci and streptococci).

  一种新型的10a-azalide化合物，其在10a-和12-位置交联，化学式如下，并且对于Hemophilus influenzae，或者对红霉素产生耐药性的细菌（例如耐药性肺炎球菌和链球菌）具有有效性。
• New Method for Preparation of Coumarins and Quinolinones via Pd-Catalyzed Intramolecular Hydroarylation of C−C Triple Bonds
  作者：Chengguo Jia、Dongguo Piao、Tsugio Kitamura、Yuzo Fujiwara

  DOI：10.1021/jo000861q

  日期：2000.11.1

  A new and general method has been developed for preparation of coumarins and quinolinones by intramolecular hydroarylation of alkynes. Various aryl alkynoates and alkynanilides undergo fast intramolecular reaction at room temperature in the presence of a catalytic amount of Pd(OAc)(2) in a mixed solvent containing trifluoroacetic acid (TFA), affording coumarins and quinolinones in moderate to excellent yields with more than 1000 turnover numbers (TON) to Pd. The methodology proved to tolerate a number of functional groups such as Br and CHO. On the basis of isotope experiments, a possible mechanism involving ethynyl chelation-assisted electrophilic metalation of aromatic C-H bonds by in-situ generated cationic Pd(II) species has been discussed. Also the involvement of vinylcationic species has been suggested.
• Novel Pd(II)- and Pt(II)-Catalyzed Regio- and Stereoselective <i>trans</i>-Hydroarylation of Alkynes by Simple Arenes
  作者：Chengguo Jia、Wenjun Lu、Juzo Oyamada、Tsugio Kitamura、Kenji Matsuda、Masahiro Irie、Yuzo Fujiwara

  DOI：10.1021/ja0005845

  日期：2000.8.1

  Efficient trans-hydroarylation of alkynes by simple arenes has been realized regio- and stereoselectively at room temperature in the presence of Pd(II) or Pt(II) catalysts and a mixed solvent containing trifluoroacetic acid (TFA). Various arenes undergo trans-hydroarylation selectively across terminal and internal C-C triple bonds-including those conjugated to CHO, COMe, CO2H, and CO2Et groups, affording kinetically controlled cis-arylalkenes predominantly in most cases, especially, in good yields for electron-rich arenes and activated alkynes. The formation of arene/alkyne 1/2 or 2/1 adducts as side products is dependent on the arenes' and alkynes' substituents, which can be suppressed in some cases by changing the catalyst, catalyst concentration, and reaction time. The Pt(II) system, PtCl2/2AgOAc/TFA, shows lower catalytic activity than Pd(OAc)(2)/TFA, but higher selectivity, giving higher yields of adducts at the same conversion. On the basis of several isotope experiments and control reactions, a possible mechanism involving electrophilic metalation of aromatic C-H bonds by in-situ-generated cationic Pd(II) and Pt(II) species leading to intermolecular trans-arylpalladation to alkynes has been discussed.
• A New Gold-Catalyzed Domino Cyclization and Oxidative Coupling Reaction
  作者：Hermann A. Wegner、Sebastian Ahles、Markus Neuburger

  DOI：10.1002/chem.200801848

  日期：——
• Sen; Kakaji, Journal of the Indian Chemical Society, 1952, vol. 29, p. 950,952
  作者：Sen、Kakaji

  DOI：——

  日期：——

表征谱图