6-(2-甲氧基乙基)-2,2,5,7-四甲基-3H-茚-1-酮 | 35944-01-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 中文名称: 6-(2-甲氧基乙基)-2,2,5,7-四甲基-3H-茚-1-酮
• 英文名称: 6-<2-methoxyethyl>-2,2,5,7-tetramethylindan-1-one
• 英文别名: pterosin I；pterozin I；6-(2-methoxyethyl)-2,2,5,7-tetramethyl-3H-inden-1-one
• CAS: 35944-01-5
• 化学式: C₁₆H₂₂O₂
• 分子量: 246.349
• InChiKey: OJOSRHYPGDXYOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(2-甲氧基乙基)-2,2,5,7-四甲基-3H-茚-1-酮 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 以90%的产率得到蕨素 Z
  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
• 作为产物：
  描述：

  2,2-dimethylpent-4-enoyl chloride 在 rhodium(II) acetate dimer 四氯化锡 、 sodium hydride 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 苯 为溶剂， 反应 21.0h， 生成 6-(2-甲氧基乙基)-2,2,5,7-四甲基-3H-茚-1-酮
  参考文献：
  名称：

  Generation and Cycloaddition Behavior of Spirocyclic Carbonyl Ylides. Application to the Synthesis of the Pterosin Family of Sesquiterpenes

  摘要：

  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.

  DOI：

  10.1021/jo951371e

文献信息

• Chemical and toxicological studies on bracken fern, Pteridium aquilinum var. latiusculum. II. Structures of pterosins, sesquiterpenes having 1-indanone skeleton.
  作者：MASAMICHI FUKUOKA、MASANORI KUROYANAGI、KUNITOSHI YOSHIHIRA、SHINSAKU NATORI

  DOI：10.1248/cpb.26.2365

  日期：——

  The structures of twenty-four sesquiterpenes isolated from the young fronds were disclosed by chemical and physical methods. The stereostructures were established as 1-22 by degradation and correlation reactions and physical data.

  通过化学和物理方法揭示了从嫩叶中分离出的二十四种倍半萜的结构。通过降解和相关反应以及物理数据，确定了立体结构为 1-22。
• USE OF PTEROSIN COMPOUNDS FOR TREATING DIABETES AND OBESITY
  申请人：Hsu Feng-Lin

  公开号：US20100190732A1

  公开（公告）日：2010-07-29

  This invention relates to the use of pterosin compounds of formula I for treating diabetes including type I and type II. Also disclosed is the use of the pterosin compounds for treating obesity.

  本发明涉及使用式I的翼龙素化合物治疗糖尿病，包括1型和2型糖尿病。还揭示了使用翼龙素化合物治疗肥胖症。
• 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
• 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.
• Ptaquiloside Z, a new toxic unstable sesquiterpene glucoside from the neotropical bracken fern pteridium aquilinum var. caudatum
  作者：Uvidelio Francisco Castillo、Makoto Ojika、Miguel Alonso-Amelot、Youji Sakagami

  DOI：10.1016/s0968-0896(98)00168-0

  日期：1998.11

  Reversed-phase HPLC fractionation, monitored by brine shrimp bioassay, led to the isolation of a new illudane-type sesquiterpene glucoside, ptaquiloside Z (2), as well. as the known bracken carcinogen ptaquiloside (1), from a bioactive aqueous extract of the neotropical bracken fern Pteridium aquilinum var. caudatum (Pteridaceae). The structure of ptaquiloside Z (2) was confirmed by spectroscopic analyses and chemical degradation. Both compounds exhibited similar toxicity (LC50 62.5 mu g/ml at 24 h and LC50 7.8 mu g/ml at 48 h) toward brine shrimp. (C) 1998 Elsevier Science Ltd. All rights reserved.