2-(2,2-Dimethyl-3-hydroxypropyl)-3-methylcyclopentene | 115512-37-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2,2-Dimethyl-3-hydroxypropyl)-3-methylcyclopentene
• 英文别名: 2,2-Dimethyl-3-(5-methylcyclopenten-1-yl)propan-1-ol
• CAS: 115512-37-3
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: HPFJBXPOFKQDMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  2-(2,2-Dimethyl-3-hydroxypropyl)-3-methylcyclopentene 在 吡啶 、 lithium iodide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 生成 2-(2,2-Dimethyl-3-iodopropyl)-3-methylcyclopentene
  参考文献：
  名称：

  分子内 Pauson-Khand 环加成反应中的非对映面选择性。戊烯的高立体选择性合成

  摘要：

  制备 de deux isomeres de triquinanes dont la structure est celle d'un cyclopenta [h] pentalene a partir demethyl-5 cyclopentene-1yl 锂和 demethyl-2 丙烯酸酯 d'aryle [de BHA ou BHT]。Cette synthese permet, a partir d'une methode deja utilisee, de parvenir au pentalenene

  DOI：

  10.1021/ja00223a069
• 作为产物：
  描述：

  2,6-Di-tert-butyl-4-methylphenyl 2,2-dimethyl-3-(5-methylcyclopentenyl)propanoate 在 乙醇 、 氨 、 sodium 作用下， 以45%的产率得到2-(2,2-Dimethyl-3-hydroxypropyl)-3-methylcyclopentene
  参考文献：
  名称：

  分子内 Pauson-Khand 环加成反应中的非对映面选择性。戊烯的高立体选择性合成

  摘要：

  制备 de deux isomeres de triquinanes dont la structure est celle d'un cyclopenta [h] pentalene a partir demethyl-5 cyclopentene-1yl 锂和 demethyl-2 丙烯酸酯 d'aryle [de BHA ou BHT]。Cette synthese permet, a partir d'une methode deja utilisee, de parvenir au pentalenene

  DOI：

  10.1021/ja00223a069

文献信息

• The Pauson-Khand reaction in triquinane synthesis: approaches to pentalenene, pentalenic acid, and silphinene
  作者：Elizabeth G. Rowley、Neil E. Schore

  DOI：10.1021/jo00051a034

  日期：1992.12

  Substituted pentynylcyclopentene precursors for the synthesis of pentalenene, pentalenic acid, and silphinene by intramolecular Pauson-Khand cycloaddition reaction have been prepared from 2-methylcyclopentanone via 5-methylcyclopentenyllithium. Conjugate addition of the latter to BHT methacrylate followed by methylation were the key steps in enyne synthesis. Reaction of 4,4-dimethyl-5-(5-methylcyclopentenyl)-1-pen e with Co2(CO)8 produces two diastereomeric triquinane enones in an overall yield of 51%, with the exo-9-methyl isomer predominating by ratio of 8:1. This material was converted into pentalenene in two steps. Pauson-Khand reaction of the TBDMS ether of 4,4-dimethyl-5-(5-methylcyclopentenyl)-1-pentyn-3-ol proceeds in 33% yield. Three of the four possible stereoisomeric products are formed, with two of them, making up ca. 80% of the product mixture, possessing the necessary exo-methyl stereochemistry at C-9 for further elaboration into pentalenic acid. A formal synthesis of the latter was completed by reduction of one of the enone isomers into a ketone which had previously been carried on to the natural product. Pd(0)-catalyzed coupling of 1-iodo-5-methylcyclopentene to 1-(trimethylsilyl)-1,4-pentadiyne and reduction over Lindlar's catalyst allowed efficient access to (Z)-1-(5-methylcyclopentenyl)-1-penten-4-yne, but the latter could not be induced to undergo Pauson-Khand cyclization, thus foiling a planned approach to silphinene.
• SCHORE, NEIL E.;ROWLEY, ELIZABETH G., J. AMER. CHEM. SOC., 110,(1988) N 15, 5224-5225
  作者：SCHORE, NEIL E.、ROWLEY, ELIZABETH G.

  DOI：——

  日期：——