3-(3,3-Dimethyl-1-propen-3-yl)cyclopentanone | 21990-91-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(3,3-Dimethyl-1-propen-3-yl)cyclopentanone
• 英文别名: 3-(2-Methylbut-3-en-2-yl)cyclopentan-1-one
• CAS: 21990-91-0
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: RXYVSMSHSDEZHV-UHFFFAOYSA-N

物化性质

• 沸点：
  206.4±9.0 °C(Predicted)
• 密度：
  0.933±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  3-(3,3-Dimethyl-1-propen-3-yl)cyclopentanone 在 甲基锂 、 四氯化钛 、 lithium chloride 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 、 正己烷 、 二甲基亚砜 为溶剂， 反应 31.83h， 生成 methyl 2-[3-(3,3-dimethyl-1-propen-3-yl)cyclopenthyl]acetate
  参考文献：
  名称：

  利用顺序分子内羟醛缩合的简明全合成信使黄酮：绝对构型的确定

  摘要：

  通过连续的分子内羟醛缩合，然后化学和非对映选择性还原共轭碳-碳双键，通过简洁地构建其齐氮烯骨架，完成了黄酮酮（一种新型的倍半萜类抗生素）的首次全合成。以2-环戊烯-1-酮为起始原料，从九步完成了这项合成工作，无需使用保护基，并具有很高的立体控制性。此外，测定天然存在albaflavenone的绝对构型为1 - [R，2小号和8小号。

  DOI：

  10.1021/ol503202d
• 作为产物：
  描述：

  5,5-dimethyl-1-vinylbicyclo[2.1.1]hexane 生成 3-(3,3-Dimethyl-1-propen-3-yl)cyclopentanone
  参考文献：
  名称：

  Reactions of isoprenoids. VII. Acid-catalyzed hydrolysis of1-(5,5-dimethylbicyclo[2.1.1]hexan-1-yl)-1,2-epoxyethane

  摘要：

  DOI：

  10.1021/jo00826a055

文献信息

• 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).
• Conjugate Addition Reactions of Allylic Copper Species Derived from Grignard Reagents: Synthetic and Spectroscopic Aspects
  作者：Bruce H. Lipshutz、Claus Hackmann

  DOI：10.1021/jo00103a042

  日期：1994.12

  A general study on the 1,4-addition chemistry of allyl, methallyl, crotyl, and prenyl Grignard-derived organocopper reagents has been conducted. While diallylic cuprates formed from such species are not effective Michael donors, the 1:1:1 combination of an allylic Grignard, CuBr.SMe(2), and Me(3)SiCl leads to high yields of 1,4-adducts. The stereo- and regiochemistry associated with the allylic ligand, where appropriate, has also been examined. Low temperature C-13 NMR studies provide insight as to the nature of these complexes.
• Reactions of isoprenoids. VII. Acid-catalyzed hydrolysis of1-(5,5-dimethylbicyclo[2.1.1]hexan-1-yl)-1,2-epoxyethane
  作者：Tadashi. Sasaki、Shoji. Eguchi、Teruhiko. Ishii

  DOI：10.1021/jo00826a055

  日期：1970.1.1
• Concise Total Synthesis of Albaflavenone Utilizing Sequential Intramolecular Aldol Condensation: Determination of Absolute Configuration
  作者：Toyoharu Kobayashi、Yutaro Kon、Hideki Abe、Hisanaka Ito

  DOI：10.1021/ol503202d

  日期：2014.12.19

  concise construction of its zizaene skeleton utilizing sequential intramolecular aldol condensation followed by chemo- and diastereoselective reduction of the conjugated carbon–carbon double bond. This synthetic work was completed in nine steps from 2-cyclopenten-1-one as a starting material without the use of protecting groups and with high stereocontrol. In addition, the absolute configuration of

  通过连续的分子内羟醛缩合，然后化学和非对映选择性还原共轭碳-碳双键，通过简洁地构建其齐氮烯骨架，完成了黄酮酮（一种新型的倍半萜类抗生素）的首次全合成。以2-环戊烯-1-酮为起始原料，从九步完成了这项合成工作，无需使用保护基，并具有很高的立体控制性。此外，测定天然存在albaflavenone的绝对构型为1 - [R，2小号和8小号。