2-vinylcyclopropylcarbaldehyde | 22823-00-3

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: 2-vinylcyclopropylcarbaldehyde
• 英文别名: trans-2-vinylcyclopropanecarboxaldehyde；trans-2-Vinyl-cyclopropylcarbaldehyd；trans-2-Vinyl-cyclopropylcarboxaldehyd；(1R,2S)-2-ethenylcyclopropane-1-carbaldehyde
• CAS: 22823-00-3；22823-01-4；24519-25-3；77210-38-9；99438-19-4
• 化学式: C₆H₈O
• 分子量: 96.1289
• InChiKey: VVRVSKFQOPUGNO-RITPCOANSA-N

物化性质

• 沸点：
  111.0±29.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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-vinylcyclopropylcarbaldehyde 在 吡啶 作用下， 反应 2.5h， 生成 trans-1-(1-acetoxy-3-phenylpropyl)-2-vinylcyclopropane
  参考文献：
  名称：

  有机铝试剂与环丙基甲基乙酸酯和 2-乙烯基环丙烷-1,1-二羧酸酯的反应

  摘要：

  研究了环丙基甲基乙酸酯的开环烷基化。7-（1-乙酰氧基庚基）降卡烷的乙酰氧基在用三烷基铝处理后被烷基取代，但反式-1-（1-乙酰氧基乙基）-2-苯基环丙烷与三烷基铝的烷基化产生反式-5-苯基- 2-烯烃。(1S,2S)-2-苯基环丙基甲基乙酸酯与三甲基铝的反应导致光学活性完全丧失，得到外消旋4-苯基-1-戊烯。在区域选择性开环下，反式-1-(1-乙酰氧基-3-苯基丙基)-2-乙烯基环丙烷与三烷基铝的烷基化反应得到 3-烷基化的反式-8-苯基-1,5-辛二烯（选择性 73-83%） . 研究了具有双羰基取代的环碳的活化乙烯基环丙烷的同共轭加成的区域和立体化学。三烷基铝以 1,5-方式加入 2-乙烯基环丙烷-1,1-二羧酸二乙酯后，得到（2-烷基-3-丁烯基）丙二酸二乙酯（选择性超过 96%）。相反...

  DOI：

  10.1246/bcsj.54.2151
• 作为产物：
  描述：

  乙基(1R,2R)-2-甲酰基环丙烷羧酸酯 在 氢氧化钾 、 lithium aluminium tetrahydride 、 正丁基锂 、 Collins oxidation agent 作用下， 以 乙醚 为溶剂， 反应 5.0h， 生成 2-vinylcyclopropylcarbaldehyde
  参考文献：
  名称：

  Kajiwara, Tadahiko; Nakatomi, Toshihiro; Sasaki, Yasushi, Agricultural and Biological Chemistry, 1980, vol. 44, # 9, p. 2099 - 2104

  摘要：

  DOI：

文献信息

• Cascade radical cyclisations with vinylcyclopropane electrophores
  作者：Gerald Pattenden、Paul Wiedenau

  DOI：10.1016/s0040-4039(97)00691-6

  日期：1997.5

  tris-(trimethylsilyl)silane (TTMSS)-AIBN gave 6 and 7 (2:1, 65%) resulting from a radical cascade 13-endo macrocyclisation followed by successive transannular cyclisations. In a similar manner, the iodo vinylcyclopropane 12a underwent triple cyclisation to a mixture of diastereoisomers of the oestrone analogue 14 (∼ 16%), but the vinylcyclopropyl ester 9a gave only the product 11 of macrocyclisation

  多烯碘化物治疗3，含有乙烯基环丙烷electrophore，用三- （三甲基硅烷基）硅烷（TTMSS）-AIBN给6和7（2：1，65％）选自自由基级联13-所得内大环化，随后连续跨环环化。以类似的方式，使碘代乙烯基环丙烷12a经历三环化，以形成雌酮类似物14的非对映异构体的混合物（〜16 ％），但是乙烯基环丙基酯9a在用TTMSS-AIBN处理时仅给出了大环化的产物11。
• The Racemization of <i>trans</i>-1,2-Divinylcyclopropane
  作者：Mannosuke Arai、Robert J. Crawford

  DOI：10.1139/v72-348

  日期：1972.7.1

  The synthesis of (−)-trans-1,2-divinylcyclopropane and the kinetics of its racemization and conversion to 1,4-cycloheptadiene, presumably through cis-1,2-divinylcyclopropane, are described. It is concluded that the ring opening is not an electrocyclic process.

  本文描述了(−)-trans-1,2-二乙烯基环丙烷的合成、其外消旋和转化为1,4-环庚二烯的动力学过程，推测其经由顺式-1,2-二乙烯基环丙烷转化而来。结论是，环的开放不是一个电环化反应。
• Hydrogen-deuterium fractionation factors for hydrogen-sp2 carbon bonds in olefins and allyl radicals
  作者：Joseph J. Gajewski、Leif P. Olson、Kenneth J. Tupper

  DOI：10.1021/ja00064a017

  日期：1993.6

  Thermally induced 3,3-shift of trans- 1,2-divinylcyclopropane, 1, and trans-1,2-bis(2',2'-dideuteriovinyl)cyclopropane, 1-d4, to cycloheptadiene has a kinetic isotope effect of 1.08 +/- 0.02/D when extrapolated to 25-degrees-C. To the extent that the transition state resembles two allyl radicals, the kinetic effect is the fractionation factor for deuterium between sp2 allyl radical carbon and sp2 olefinic carbon. AM1 calculations on allyl radicals reveal a similar fractionation factor. The new value for the FF of allyl radical requires a correction to previously developed linear free energy relationships for kinetic and equilibrium isotope effect in 3,3-shifts and Diels-Alder reactions. The corrections are moderate, altering the previously determined extent of bond breaking and bond making by up to 50% only when there is little bond making, but do not alter the relative extents of bond making and breaking in the large number of compounds examined.
• Synthesis of vinylcyclopropanes by intramolecular epoxide ring opening. Application for an enantioselective synthesis of dictyopterene A
  作者：Frank Narjes、Oliver Bolte、Detlef Icheln、Wilfried A. Koenig、Ernst Schaumann

  DOI：10.1021/jo00055a014

  日期：1993.1

  The reaction of functionalized oxiranes 1 with the sulfur- or silicon-stabilized anions 2 provides beta-heteroatom-substituted gamma,delta-unsaturated epoxides 5 with, for 5e,f, a trans C=C moiety. A cis compound 9 is obtained using acetylide anion 2c via 7 and subsequent partial hydrogenation of the C=C bond in the intermediate oxirane 8. Regiospecific anion generation in 5,9 is achieved by deprotonation, reductive desulfurization, and desilylation, respectively. The resulting anions 10 cyclize to 1-(hydroxyalkyl)-2-vinylcyclopropanes 11 by a stereochemically controlled S(N)i Process. Starting from the optically active epoxide 1b, the approach allows synthesis of cyclopropane 11b with (1S,2R) configuration at the ring carbon atoms. This compound can be further elaborated to the algae sex pheromone dictyopterene A which is obtained along with the unnatural Z diastereomer.
• Synthese, equilibre tautomere et pyrolyse de l'hydroxy-6 hexene-4 al cis
  作者：François Collonges、Ge´rard Descotes

  DOI：10.1016/s0040-4039(01)95919-2

  日期：1973.1