cis-2-Vinyl-cyclopropylcarbaldehyd | 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: cis-2-Vinyl-cyclopropylcarbaldehyd
• 英文别名: (1R,2R)-2-ethenylcyclopropane-1-carbaldehyde
• CAS: 22823-00-3
• 化学式: C₆H₈O
• 分子量: 96.1289
• InChiKey: VVRVSKFQOPUGNO-WDSKDSINSA-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：

  cis-2-Vinyl-cyclopropylcarbaldehyd 在 titanium(IV) isopropylate 、 四甲基乙二胺 、 叔丁基锂 、 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.25h， 生成 6-vinylcyclohepta-1,4-diene
  参考文献：
  名称：

  Pericyclic reactions in nature: Synthesis and Cope rearrangement of thermolabile bis-alkenylcyclopropanes from female gametes of marine brown algae (Phaeophyceae)

  摘要：

  The biosyntheses of the 6-substituted cyclohepta-1,4-dienes dictyotene (1), ectocarpene (2), desmarestene (3), vinylcycloheptadiene (4) and lamoxirene (5) involve a spontaneous Cope rearrangement of thermolabile bis-alkenylcyclopropane precursors like 16, 10, 26 and 30. The unstable precursors and the rearranged cycloheptadienes were synthesised from the chiral 2-iodovinylcyclopropane 12 using Pd-0 or Cu-1 catalysed approaches. Activation parameters of the Cope rearrangements were determined. Bioassays with pre-ectocarpene 10 established the thermolabile cyclopropane (1R,2R)-10, rather than the cyclohepta-1,4-diene(6S)-2, as the genuine pheromone of the brown alga Ectocarpus siliculosus. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00886-7
• 作为产物：
  描述：

  [2-(hydroxymethyl)cyclopropyl]methanol 在 吡啶 、 chromium(VI) oxide 、 正丁基锂 、 Celite 、 水 、 sodium acetate 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 51.33h， 生成 cis-2-Vinyl-cyclopropylcarbaldehyd
  参考文献：
  名称：

  Secondary deuterium kinetic isotope effects at the termini of cis-1,2-divinylcyclopropane and cis-1,2-divinylcyclobutane in their 3,3-sigmatropic shifts: evidence for different transition-state structures

  摘要：

  DOI：

  10.1021/jo00289a050

文献信息

• Cascade Cope/Winstein Rearrangements: Synthesis of Azido-Cycloheptadienes from Dialkenylcyclopropanes Possessing a Vinyl Azide
  作者：Thomas Abegg、Janine Cossy、Christophe Meyer

  DOI：10.1021/acs.orglett.2c01888

  日期：2022.7.15

  2-Dialkenylcyclopropanes incorporating a vinyl azide, generated by Knoevenagel condensations between the corresponding cyclopropanecarbaldehydes and α-azido ketones, undergo cascade Cope and Winstein [3,3]-sigmatropic rearrangements, under mild conditions. The sequence allows access to diversely substituted 1,4-cycloheptadienes armed with a secondary allylic azide with up to three stereocenters.

  顺式-1,2-二烯基环丙烷包含乙烯基叠氮化物，由相应的环丙烷甲醛和 α-叠氮基酮之间的 Knoevenagel 缩合产生，在温和条件下发生级联 Cope 和 Winstein [3,3]-σ 重排。该序列允许使用具有多达三个立体中心的二级烯丙基叠氮化物的多种取代的 1,4-环庚二烯。
• Synthese et isomerisations thermique ou ionique de vinylcyclopropylcarbinols
  作者：G. Descotes、A. Menet、F. Collonges

  DOI：10.1016/s0040-4020(01)93425-8

  日期：1973.1
• 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
• Secondary deuterium kinetic isotope effects at the termini of cis-1,2-divinylcyclopropane and cis-1,2-divinylcyclobutane in their 3,3-sigmatropic shifts: evidence for different transition-state structures
  作者：Joseph J. Gajewski、Christopher M. Hawkins、Jose L. Jimenez

  DOI：10.1021/jo00289a050

  日期：1990.1
• Pericyclic reactions in nature: Synthesis and Cope rearrangement of thermolabile bis-alkenylcyclopropanes from female gametes of marine brown algae (Phaeophyceae)
  作者：Georg Pohnert、Wilhelm Boland

  DOI：10.1016/s0040-4020(97)00886-7

  日期：1997.10

  The biosyntheses of the 6-substituted cyclohepta-1,4-dienes dictyotene (1), ectocarpene (2), desmarestene (3), vinylcycloheptadiene (4) and lamoxirene (5) involve a spontaneous Cope rearrangement of thermolabile bis-alkenylcyclopropane precursors like 16, 10, 26 and 30. The unstable precursors and the rearranged cycloheptadienes were synthesised from the chiral 2-iodovinylcyclopropane 12 using Pd-0 or Cu-1 catalysed approaches. Activation parameters of the Cope rearrangements were determined. Bioassays with pre-ectocarpene 10 established the thermolabile cyclopropane (1R,2R)-10, rather than the cyclohepta-1,4-diene(6S)-2, as the genuine pheromone of the brown alga Ectocarpus siliculosus. (C) 1997 Elsevier Science Ltd.