Pterosin H | 39004-41-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: Pterosin H
• 英文别名: pterozin H；6-(2-chloroethyl)-2,2,5,7-tetramethyl-3H-inden-1-one
• CAS: 39004-41-6
• 化学式: C₁₅H₁₉ClO
• 分子量: 250.768
• InChiKey: CPNGMVOUDSBLOG-UHFFFAOYSA-N

物化性质

• 物理描述：
  Solid
• 熔点：
  87.5-88°C

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  蕨素 Z 在 三苯基膦 作用下， 以 四氯化碳 为溶剂， 反应 17.0h， 以74%的产率得到Pterosin H
  参考文献：
  名称：

  An efficient synthesis of pterosin C and other pterosins

  摘要：

  已经开发出了一种通用的合成途径来制备蕨类植物中存在的对位香豆素类化合物——翅果酸，具体来说就是欧洲蕨（Pteridium aquilinum）。该合成途径的示例是通过使用甲基丙烯酸氯对2-(2,6-二甲基苯基)乙醇的甲基醚进行弗里德尔-克拉夫茨双取代反应来合成(2S,3S)-翅果酸C。将得到的1,3-茚二酮脱甲基，并在乙酸和乙酸钠的存在下用锌和乙酸还原，得到了翅果酸C二醋酸酯的消旋顺式和反式异构体的混合物，该混合物经水解得到了相应的翅果酸。通过S-(+)-α-苯基丁酸酯的分离和解析，得到了(2S,3S)-翅果酸C和(2R,3R)-翅果酸C。其他翅果酸则是从1,3-茚二酮以消旋混合物的形式制备的。

  DOI：

  10.1139/v84-334

文献信息

• Synthesis and antispasmodic activity of nature identical substituted indanes and analogues
  作者：H Sheridan、S Lemon、N Frankish、P McArdle、T Higgins、JP James、P Bhandari

  DOI：10.1016/0223-5234(90)90185-6

  日期：1990.9
• Generation and Cycloaddition Behavior of Spirocyclic Carbonyl Ylides. Application to the Synthesis of the Pterosin Family of Sesquiterpenes
  作者：Albert Padwa、Erin A. Curtis、Vincent P. Sandanayaka

  DOI：10.1021/jo951371e

  日期：1996.1.1

  The Rh(II)-catalyzed reaction of 1-acetyl-1-(diazoacetyl)cyclopropane and ethyl 3-(1-acetyl-cyclopropyl)-2-diazo-3-oxopropiolate with various dipolarophiles afforded dipolar cycloadducts in good yield. The reaction involves the formation of a rhodium carbenoid and subsequent transannular cyclization of the electrophilic carbon onto the adjacent keto group to generate a five-membered cyclic carbonyl ylide which undergoes a subsequent dipolar cycloaddition reaction. The regiochemical results encountered can be rationalized on the basis of FMO considerations. For carbonyl ylides, the HOMO dipole is dominant for reactions with electron deficient dipolarophiles, while the LUMO becomes important for cycloaddition to more electron rich species. A short synthesis of several members of the pterosin family of sesquiterpenes is described in which the key step involves a dipolar cycloaddition using a carbonyl ylide. The Rh(II)-catalyzed reaction of 1-acetyl-1-(diazoacetyl)-cyclopropane with cyclopentenone afforded a dipolar cycloadduct in good yield as a 4:1 mixture of diastereomers. Treatment of the major cycloadduct with triphenylphosphonium bromide in the presence of sodium hydride gave the expected Wittig product. The reaction of this compound with acid in the presence of various solvents gave rise to several members of the pterosin family. The overall sequence of reactions can best be described as proceeding by an initial oxy-bridge ring opening followed by dehydration and a subsequent acid-catalyzed cyclopropyl ring opening. The facility of the process is undoubtedly related to the aromaticity gained in the final step.
• An efficient dipolar-cycloaddition route to the pterosin family of sesquiterpenes
  作者：Erin A. Curtis、Vincent P. Sandanayaka、Albert Padwa

  DOI：10.1016/0040-4039(95)00209-u

  日期：1995.3

  A short synthesis of several members of the pterosin family of sesquiterpenes is described in which the key step involves a dipolar-cycloaddition using a carbonyl ylide.
• SHERIDAN, H.;LEMON, S.;FRANKISH, N.;MCARDLE, P.;HIGGINS, T.;JAMES, J. P.;+, EUR. J. MED. CHEM., 25,(1990) N, C. 603-608
  作者：SHERIDAN, H.、LEMON, S.、FRANKISH, N.、MCARDLE, P.、HIGGINS, T.、JAMES, J. P.、+

  DOI：——

  日期：——
• An efficient synthesis of pterosin C and other pterosins
  作者：Kam-Mui Eva Ng、Trevor C. McMorris

  DOI：10.1139/v84-334

  日期：1984.10.1

  A versatile synthetic route to pterosins, sesquiterpenoid indanones present in bracken, Pteridiumaquilinum, has been developed. The route is exemplified by the synthesis of (2S,3S)-pterosin C by Friedel–Crafts bisacylation of the methyl ether of 2-(2,6-dimethylphenyl)ethanol with methylmalonyl chloride. Demethylation of the resulting 1,3-indandione and reduction with zinc and acetic acid in the presence of acetic anhydride and sodium acetate afforded a mixture of racemic cis and trans isomers of pterosin C diacetate, which was hydrolysed to the corresponding pterosins. Separation and resolution via the S-(+)-α-phenylbutyric esters gave (2S,3S)-pterosin C and (2R,3R)-pterosin C. Other pterosins were prepared as racemates from the 1,3-indandione.

  已经开发出了一种通用的合成途径来制备蕨类植物中存在的对位香豆素类化合物——翅果酸，具体来说就是欧洲蕨（Pteridium aquilinum）。该合成途径的示例是通过使用甲基丙烯酸氯对2-(2,6-二甲基苯基)乙醇的甲基醚进行弗里德尔-克拉夫茨双取代反应来合成(2S,3S)-翅果酸C。将得到的1,3-茚二酮脱甲基，并在乙酸和乙酸钠的存在下用锌和乙酸还原，得到了翅果酸C二醋酸酯的消旋顺式和反式异构体的混合物，该混合物经水解得到了相应的翅果酸。通过S-(+)-α-苯基丁酸酯的分离和解析，得到了(2S,3S)-翅果酸C和(2R,3R)-翅果酸C。其他翅果酸则是从1,3-茚二酮以消旋混合物的形式制备的。