2-(allyloxymethyl)-3-benzoylcyclopropanecarbaldehyde

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(allyloxymethyl)-3-benzoylcyclopropanecarbaldehyde
• 英文别名: 2-benzoyl-3-(prop-2-enoxymethyl)cyclopropane-1-carbaldehyde
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: DKOFJKUPMAFYGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  18.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (benzoylmethylene)dimethylsulfurane 、 (2E)-4-(allyloxy)but-2-enal 在 (-)-5-[(S)-indoline-2-yl]tetrazole 作用下， 以 氯仿 为溶剂， 生成 (1R,2R,3S)-2-(allyloxymethyl)-3-benzoylcyclopropanecarbaldehyde 、 2-(allyloxymethyl)-3-benzoylcyclopropanecarbaldehyde
  参考文献：
  名称：

  Tetrazolic Acid Functionalized Dihydroindol:  Rational Design of a Highly Selective Cyclopropanation Organocatalyst

  摘要：

  Herein we wish to report our development of an improved catalyst (S)-(-)-indoline-2-yl-1H-tetrazole (1) for the enantioselective organocatalyzed cyclopropanation of alpha,beta-unsaturated aldehydes with sulfur ylides. The new organocatalyst readily facilitates the enantioselective organocatalytic cyclopropanation, providing cyclized product in excellent diastereoselectivities ranging from 96% to 98% along with enantioselectivities exceeding 99% enantiomeric excess for all reacted alpha,beta-unsaturated aldehydes. The new catalyst provides the best results so far reported for intermolecular enantioselective organocatalyzed cyclopropanation.

  DOI：

  10.1021/jo070519e

文献信息

• Tetrazolic Acid Functionalized Dihydroindol:  Rational Design of a Highly Selective Cyclopropanation Organocatalyst
  作者：Antti Hartikka、Per I. Arvidsson

  DOI：10.1021/jo070519e

  日期：2007.7.1

  Herein we wish to report our development of an improved catalyst (S)-(-)-indoline-2-yl-1H-tetrazole (1) for the enantioselective organocatalyzed cyclopropanation of alpha,beta-unsaturated aldehydes with sulfur ylides. The new organocatalyst readily facilitates the enantioselective organocatalytic cyclopropanation, providing cyclized product in excellent diastereoselectivities ranging from 96% to 98% along with enantioselectivities exceeding 99% enantiomeric excess for all reacted alpha,beta-unsaturated aldehydes. The new catalyst provides the best results so far reported for intermolecular enantioselective organocatalyzed cyclopropanation.