4-(5-oxo-1-hexenyl)benzaldehyde | 186751-95-1

• 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: 4-(5-oxo-1-hexenyl)benzaldehyde
• 英文别名: 4-(5-oxohex-1-enyl)benzaldehyde
• CAS: 186751-95-1
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: FCEIQTGFUQDSFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(Sn(C4H9)3)-1.2-C2B10H11 、 4-(5-oxo-1-hexenyl)benzaldehyde 在 tris(dibenzylideneacetone)dipalladium(0) * CHCl3 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 为溶剂， 以69%的产率得到6-[4-(o-carboranylhydroxymethyl)phenyl]-5-hexen-2-one
  参考文献：
  名称：

  Synthetic utility of o-carborane: novel protective group for aldehydes and ketones

  摘要：

  o-Carborane acts as a novel protective group of carbonyl compounds. The reaction of lithiocarborane 2, which was prepared in an essentially quantitative yield from o-carborane and n-butyllithium, with aldehydes or ketones 1 gave the corresponding addition products, o-carboranyl methanol derivatives 3, in high yields. Cleavage of o-carborane from 3 was carried out by treating 3 with catalytic amounts of KOH in THF/H2O (100/1), giving the corresponding aldehydes or ketones in good to high yields along with recovered o-carborane. Accordingly, o-carborane may be utilized as a protective group stable under protic and Lewis acid conditions. Selective alkylation of an ester group, selective reduction of an ester, and selective alkylation of a ketone in the presence of an aldehyde are accomplished by using o-carborane protective groups. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(98)00922-x

文献信息

• Synthetic utility of o-carborane: novel protective group for aldehydes and ketones
  作者：Hiroyuki Nakamura、Kouichi Aoyagi、Yoshinori Yamamoto

  DOI：10.1016/s0022-328x(98)00922-x

  日期：1999.2

  o-Carborane acts as a novel protective group of carbonyl compounds. The reaction of lithiocarborane 2, which was prepared in an essentially quantitative yield from o-carborane and n-butyllithium, with aldehydes or ketones 1 gave the corresponding addition products, o-carboranyl methanol derivatives 3, in high yields. Cleavage of o-carborane from 3 was carried out by treating 3 with catalytic amounts of KOH in THF/H2O (100/1), giving the corresponding aldehydes or ketones in good to high yields along with recovered o-carborane. Accordingly, o-carborane may be utilized as a protective group stable under protic and Lewis acid conditions. Selective alkylation of an ester group, selective reduction of an ester, and selective alkylation of a ketone in the presence of an aldehyde are accomplished by using o-carborane protective groups. (C) 1999 Elsevier Science S.A. All rights reserved.