2-(buta-2,3-dienyl)benzaldehyde | 1245795-76-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(buta-2,3-dienyl)benzaldehyde
• CAS: 1245795-76-9
• 化学式: C₁₁H₁₀O
• 分子量: 158.2
• InChiKey: HUHFBNIOSBTDJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  1-乙炔基萘 、 2-(buta-2,3-dienyl)benzaldehyde 在 (S)-(-)-5,5-双(二苯膦基)-4,4-双-1,3-苯并间二氧杂环戊烯 、 acetylacetonatobis(ethylene)rhodium(I) 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以64%的产率得到(1S,2R)-2-(4-(naphthalen-1-yl)but-1-en-3-yn-2-yl)indan-1-ol
  参考文献：
  名称：

  Rhodium-catalyzed enantioselective alkynylative cyclization of allenyl aldehydes with terminal alkynes

  摘要：

  Asymmetric addition of terminal alkynes to allenyl aldehydes took place in the presence of an acetylacetonate complex [Rh(acac)L*] (L* = binap or segphos) as a catalyst to give indanol derivatives in high yields with high regio- and enantioselectivity. The acetylacetonate (acac) ligand on the rhodium is important for the selective formation of the indanol derivatives. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.039
• 作为产物：
  描述：

  2-(2-(buta-2,3-dienyl)phenyl)-1,3-dioxolane 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以1.6 g的产率得到2-(buta-2,3-dienyl)benzaldehyde
  参考文献：
  名称：

  Rhodium-catalyzed enantioselective alkynylative cyclization of allenyl aldehydes with terminal alkynes

  摘要：

  Asymmetric addition of terminal alkynes to allenyl aldehydes took place in the presence of an acetylacetonate complex [Rh(acac)L*] (L* = binap or segphos) as a catalyst to give indanol derivatives in high yields with high regio- and enantioselectivity. The acetylacetonate (acac) ligand on the rhodium is important for the selective formation of the indanol derivatives. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.039

文献信息

• Enantioselective Intermolecular [2 + 2 + 2] Cycloadditions of Ene–Allenes with Allenoates
  作者：Andrew T. Brusoe、Rahul V. Edwankar、Erik J. Alexanian

  DOI：10.1021/ol303024q

  日期：2012.12.7

  An enantioselective [2 + 2 + 2] cycloaddition of ene-allenes with allenoates is described, which transforms simple pi-components into stereochemically complex carbocycles in a single step. The rhodium(I)-catalyzed cycloaddition proceeds with good levels of enantioselectivity, and with high levels of regio-, chemo-, and diastereoselectivity. Our results are consistent with a mechanism involving an enantioselective intermolecular allene-allene oxidative coupling.
• Rhodium-catalyzed enantioselective alkynylative cyclization of allenyl aldehydes with terminal alkynes
  作者：Xun-Xiang Guo、Takahiro Sawano、Takahiro Nishimura、Tamio Hayashi

  DOI：10.1016/j.tetasy.2010.04.039

  日期：2010.7

  Asymmetric addition of terminal alkynes to allenyl aldehydes took place in the presence of an acetylacetonate complex [Rh(acac)L*] (L* = binap or segphos) as a catalyst to give indanol derivatives in high yields with high regio- and enantioselectivity. The acetylacetonate (acac) ligand on the rhodium is important for the selective formation of the indanol derivatives. (C) 2010 Elsevier Ltd. All rights reserved.