2-methyl-3-(2-propenyl)cyclopentanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-3-(2-propenyl)cyclopentanone
• 英文别名: 3-allyl-2-methylcyclopentanone；2-Methyl-3-prop-2-enylcyclopentan-1-one
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: KCLFZDVIQFVTLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methyl-3-(2-propenyl)cyclopentanone 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 正丁基锂 、 sodium methylate 、 对甲苯磺酸 、 二异丙胺 、 原甲酸三乙酯 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 27.67h， 生成 2-[[(8R,9R)-9-methyl-8-(3-methylbut-2-enyl)-1,4-dioxaspiro[4.4]nonan-9-yl]methyl]hex-5-enenitrile
  参考文献：
  名称：

  ophiobolin A和variecolin的基本骨架的构建†

  摘要：

  麦竹叶林和水松木类型的酯类萜类化合物属于含环辛烷的天然产物。两种酯类萜都具有挑战性的结构和有吸引力的生物活性。我们设想，关键的串联环闭合二烯的复分解可以提供ophiobolin A和variecolin的基本骨架。我们在此报告了有效地提供5-8-5和5-8-6-5环的二烯的详细反应性。

  DOI：

  10.1039/c3ob41693c
• 作为产物：
  描述：

  甲基环戊烯醇酮 、 烯丙基溴化镁 在 copper(I) bromide dimethylsulfide complex 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.0h， 以96%的产率得到2-methyl-3-(2-propenyl)cyclopentanone
  参考文献：
  名称：

  ophiobolin A和variecolin的基本骨架的构建†

  摘要：

  麦竹叶林和水松木类型的酯类萜类化合物属于含环辛烷的天然产物。两种酯类萜都具有挑战性的结构和有吸引力的生物活性。我们设想，关键的串联环闭合二烯的复分解可以提供ophiobolin A和variecolin的基本骨架。我们在此报告了有效地提供5-8-5和5-8-6-5环的二烯的详细反应性。

  DOI：

  10.1039/c3ob41693c

文献信息

• A synthetic approach to the functionalized hydroazulene core of guanacastepenes and heptemerenes
  作者：Karol Michalak、Michał Michalak、Jerzy Wicha

  DOI：10.1016/j.tetlet.2008.09.082

  日期：2008.11

  A functionalized hydroazulene derivative has been synthesized efficiently from 2-methylcyclopent-2-en-1-one as a part of a study oriented toward the total synthesis of diterpenoids of biological significance, guanacastepenes, and heptemerones.

  已经从2-甲基环戊-2-en-1-one有效地合成了官能化的水az烯衍生物，该研究的方向是具有生物学意义的二萜类化合物，鸟苷和庚酮的全合成。
• Allylbarium Reagents: Unprecedented Regio- and Stereoselective Allylation Reactions of Carbonyl Compounds
  作者：Akira Yanagisawa、Shigeki Habaue、Katsutaka Yasue、Hisashi Yamamoto

  DOI：10.1021/ja00093a010

  日期：1994.7

  The first direct preparation of allylbarium reagents by reaction of insitu generated reactive barium with various allylic chlorides and their new and unexpected selective allylation reactions with carbonyl compounds are disclosed. Highly reactive barium was readily prepared by the reduction of barium iodide with 2 equiv of lithium biphenylide in dry THF at room temperature. A variety of carbonyl compounds reacted with barium reagents generated from (E)- or (Z)-allylic chlorides in THF at -78 degrees C. All reactions resulted in high yields with remarkable alpha-selectivities not only with aldehydes but also with ketones. The double bond geometry of the starting allylic chloride was completely retained in each case. Stereochemically homogeneous (E)- and (Z)beta,gamma-unsaturated carboxylic acids were easily prepared in good yields by highly alpha-selective carboxylation of allylic barium reagents with carbon dioxide. A selective Michael addition reaction with alpha,beta-unsaturated cycloalkanone was also achieved using an allylbarium reagent. Treatment of 2-cyclopentenone (1 equiv) with allylbarium chloride (2 equiv) in THF at -78 degrees C for 20 min afforded 3-allylcyclopentanone in 94% yield with a 1,4/1,2 ratio of >99/1. Furthermore, the in situ generated barium enolate was efficiently trapped with various kinds of electrophiles (Me(2)C=CHCH2Br, (C5H11CHO)-C-n, and CH3COCl).
• HAYASHI MASAJI; MUKAIYAMA TERUAKI, CHEM. LETT.,(1987) N 2, 289-292
  作者：HAYASHI MASAJI、 MUKAIYAMA TERUAKI

  DOI：——

  日期：——
• Construction of the basic skeleton of ophiobolin A and variecolin
  作者：Ke Li、Cheng Wang、Gang Yin、Shuanhu Gao

  DOI：10.1039/c3ob41693c

  日期：——

  Ophiobolin and variecolin type sesterterpenoids belong to cyclooctane-containing natural products. Both sesterterpenoids have challenging structures and appealing biological activities. We envisioned that a key tandem ring closing metathesis of dienynes could provide the basic skeleton of ophiobolin A and variecolin. We report herein the detailed reactivities of the dienynes which furnished the 5-8-5

  麦竹叶林和水松木类型的酯类萜类化合物属于含环辛烷的天然产物。两种酯类萜都具有挑战性的结构和有吸引力的生物活性。我们设想，关键的串联环闭合二烯的复分解可以提供ophiobolin A和variecolin的基本骨架。我们在此报告了有效地提供5-8-5和5-8-6-5环的二烯的详细反应性。