1-(2-甲基-2-丙烯基)-2-环己烯-1-醇 | 5674-03-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2-甲基-2-丙烯基)-2-环己烯-1-醇
• 英文名称: 1-(2-methyl-2-propenyl)-2-cyclohexen-1-ol
• 英文别名: 3-Hydroxy-3-<2-methyl-propen-(2)-yl>-cyclohexen；1-(2-Methyl-2-propenyl)-cyclohex-2-en-1-ol；3-hydroxy-3-(2-methylprop-2-enyl)-cyclohexene；1-(2-Methylprop-2-enyl)cyclohex-2-en-1-ol
• CAS: 5674-03-3
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: PPDJKQXVAZFWDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  1-(2-甲基-2-丙烯基)-2-环己烯-1-醇 在 sodium tetrahydroborate 、 mercury(II) trifluoroacetate 作用下， 生成 3-(2-Methyl-1-propen-3-yl)cyclohexanone
  参考文献：
  名称：

  易位辅助氧化三氟乙酸汞的化学计量和定量催化

  摘要：

  在室温下，将1,5-己二烯-3-醇叔化成35-90％的δ-乙烯酮，在两种条件下收率：用一摩尔当量的三氟乙酸汞处理，然后使中间的α-水银脱汞酮与硼氢化钠；用0.2摩尔当量的三氟乙酸锂或三氟甲磺酸锂处理。反应是高度立体选择性的，酮的E异构体占产物的80-95％。在第二条件下观察到最高的选择性。

  DOI：

  10.1016/0040-4020(84)85011-5
• 作为产物：
  描述：

  2-环己烯-1-酮 、 2-Methylallylmagnesium Chloride 在 copper(l) chloride 作用下， 生成 1-(2-甲基-2-丙烯基)-2-环己烯-1-醇
  参考文献：
  名称：

  The Reaction of Δ²-Cyclohexenone with β-Methylallylmagnesium Chloride and Isobutylmagnesium Chloride. The Effect of Added Cuprous Chloride¹

  摘要：

  DOI：

  10.1021/jo01340a506

文献信息

• Process for the preparation of 8-ethylenic carbonyl compounds
  申请人：Rhone-Poulenc Sante

  公开号：US04421934A1

  公开（公告）日：1983-12-20

  Process for the preparation of .delta.-ethylenic carbonyl compounds of the formula (I) by the oxy-Cope rearrangement of a diethylenic alcohol of the formula (II), in the presence of a mercuric salt: in formulae (I) and (II), R.sub.1, R.sub.2, R.sub.4, R.sub.5 and R.sub.6, which are identical or different, represent a hydrogen atom or an acyclic hydrocarbon radical and R.sub.3 represents an acyclic hydrocarbon radical, it being understood that R.sub.1 and R.sub.3 can together form a trimethylene radical, or alternatively that R.sub.3 and R.sub.4 can together form an alkylene radical containing 3 to 20 carbon atoms. ##STR1##

  以汞盐存在下，通过二乙烯醇的氧-科普重排反应，制备公式(I)的.delta.-烯丙酮化合物的过程：在公式(I)和(II)中，R.sub.1、R.sub.2、R.sub.4、R.sub.5和R.sub.6，它们相同或不同，表示氢原子或无环烃基，R.sub.3表示无环烃基，其中R.sub.1和R.sub.3可以共同形成三亚甲基基团，或者R.sub.3和R.sub.4可以共同形成含3至20个碳原子的烷基基团。##STR1##
• 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).
• Electrochemical allylation of carbonyl compounds using nickel catalyst and zinc(II) species
  作者：Sylvie Durandetti、Soline Sibille、Jacques Perichon

  DOI：10.1021/jo00270a033

  日期：1989.4
• Reaction of .pi.-allylnickel bromide complexes with ketones and aldehydes. Synthesis of .alpha.-methylene-.gamma.-butyrolactones
  作者：L. S. Hegedus、S. D. Wagner、E. L. Waterman、K. Siirala-Hansen

  DOI：10.1021/jo00893a012

  日期：1975.3
• DURANDETTI, SYLVIE;SIBILLE, SOLINE;PERICHON, JACQUES, J. ORG. CHEM., 54,(1989) N, C. 2198-2204
  作者：DURANDETTI, SYLVIE、SIBILLE, SOLINE、PERICHON, JACQUES

  DOI：——

  日期：——