4,4-dimethyl-2-isopropenylcyclopentylacetic acid | 210752-27-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4,4-dimethyl-2-isopropenylcyclopentylacetic acid
• 英文别名: 2-(4,4-Dimethyl-2-prop-1-en-2-ylcyclopentyl)acetic acid
• CAS: 210752-27-5
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: YDIWVOHPQVJBJN-UHFFFAOYSA-N

物化性质

• 沸点：
  292.1±9.0 °C(Predicted)
• 密度：
  0.958±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4-dimethyl-2-isopropenylcyclopentylacetic acid 在 草酰氯 、 二甲基硫 、 臭氧 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 24.25h， 生成 (1aα,3aβ,6aβ,6bα)-(+/-)-methyl 3a,4,5,6,6a,6b-hexahydro-5,5,6b-trimethyl-2<<(trifluoromethyl)sulfonyl>oxy>cyclopropindene-1a(1H)-carboxylate
  参考文献：
  名称：

  Total synthesis of some marasmane and lactarane sesquiterpenes.

  摘要：

  A general and efficient synthetic route to the marasmane sesquiterpenes (+/-)-isovelleral (2) and (+/-)-stearoylvelutinal (1b) is described. Total syntheses of two other naturally occurring sesquiterpenes, deconjugated anhydrolactarorufin A (5) and lactarorufin A (6), were achieved using an acid-catalyzed ring expansion of lactone 25. All four syntheses are highly stereoselective and do not require the use of any protecting groups. Finally, the protic acid-catalyzed degradation of velutinal (1a) was investigated in an effort to chemically induce the biologically important conversion of velutinal (1a) to isovelleral (2). The experimental results thus obtained indicate that an enzymatic mechanism for the key transformation of velutinal (1a) into isovelleral (2) is more plausible than one that is acid-catalyzed.

  DOI：

  10.1021/jo00048a036
• 作为产物：
  描述：

  3,3,6-trimethyl-5-heptenal 在 hydroxide 作用下， 生成 4,4-dimethyl-2-isopropenylcyclopentylacetic acid
  参考文献：
  名称：

  Synthetic Studies towards Compounds Related to Sterpurene and Protoilludene.

  摘要：

  As part of synthetic strategies towards the sesquiterpenes 6-protoilludene and sterpurene the intramolecular aldol condensation of 1-(2-oxopropyl)-2-acetyl-4,4-dimethylcyclopentane was studied in detail. Mixtures of 5,8,8-trimethylbicyclo[4.3.0]-4-nonen-3-one and 4,8,8-trimethylbicyclo[4.3.0]-3-nonen-2-one were formed. The reaction was carried out under different acidic and basic conditions, giving the two compounds in ratios varying from 1:1 to 12:1. The best conditons were found to be methanesulfonic acid in methanol. The preparation of trans-5,8,8-trimethylbicyclo[4.3.0]-4-nonen-3-one by our route in about 70% overall yield constitutes formally a new synthesis of sterpurene.

  DOI：

  10.3891/acta.chem.scand.52-0806

文献信息

• Synthetic Studies towards Delta6-Protoilludene. A Formal Synthesis.
  作者：Trond Vidar Hansen、Stephen M'dachi、Lars Skattebøl、Yngve Stenstrøm

  DOI：10.3891/acta.chem.scand.52-1373

  日期：——

  A synthetic strategy towards Delta(6)-protoilludene included an intramolecular allene-ene cycloaddition reaction as a key step; however, the thermal reaction furnished a stereoisomeric mixture of 9-methyl-1,4,4,8-tetramethyltricyclo[6.2.0.0(2,6)]decane, which has a ring assembly isomeric with that of the target molecule. Another approach to Delta(6)-protoilludene required cis-4,4-dimethyl-2-isopropenylcyclopentylacetic acid, which was obtained from the mixture of stereoisomers by column chromatographic separation of the corresponding iodolactones. The cis-acid was further converted into cis-ethyl 4-(2-isopropenyl-4,4-dimethylcyclopentyl)-3-methyl-2-butenoate which has previously been transformed by others into Delta(6)-protoilludene. Hence, our approach constitutes formally a new synthesis of Delta(6)-protoilludene.
• THOMPSON, SCOTT K.;HEATHCOCK, CLAYTON H., J. ORG. CHEM., 55,(1990) N 10, C. 783
  作者：THOMPSON, SCOTT K.、HEATHCOCK, CLAYTON H.

  DOI：——

  日期：——
• Total synthesis of (.+-.)-isovelleral, a mutagenic sesquiterpene dialdehyde from Lactarius vellereus
  作者：Scott K. Thompson、Clayton H. Heathcock

  DOI：10.1021/jo00297a009

  日期：1990.5