3-乙氧基螺[3.5]-2-壬烯-1-酮 | 10576-21-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯酯类
• 中文名称: 3-乙氧基螺[3.5]-2-壬烯-1-酮
• 中文别名: 3-乙氧基螺[3.5]壬-2-烯-1-酮
• 英文名称: 3-ethoxyspiro[3.5]non-2-en-1-one
• 英文别名: 1-ethoxyspiro[3.5]non-1-en-3-one
• CAS: 10576-21-3
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: JPBFQEGAYWNUJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  3-乙氧基螺[3.5]-2-壬烯-1-酮 在 盐酸 、 N-碘代丁二酰亚胺 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.08h， 生成 ethyl (2S)-3-{4-[(3,5-dichloroisonicotinoyl)amino]phenyl}-2-(3-oxo-2-pyridin-3-yl-spiro[3.5]non-1-en-1-ylamino)propanoate
  参考文献：
  名称：

  Efficient Synthesis of 3-Aminocyclobut-2-en-1-ones:  Squaramide Surrogates as Potent VLA-4 Antagonists

  摘要：

  [GRAPHICS]A novel series of uniquely functionalized 3-aminocyclobut-2-en-1-ones has been prepared by facile condensation of a variety of cyclobuta-1,3-diones with a phenylalanine-derived primary amine. These systems subsequently lend themselves to substitution at C-2 by reaction with a variety of electrophilic reagents including N-halosuccinimides, sulfenyl chlorides, and Eschenmoser's salt. Compounds from this novel series are potent antagonists of VLA-4.

  DOI：

  10.1021/ol034701n
• 作为产物：
  描述：

  乙氧基乙炔 、 环己甲酰氯 在 三乙胺 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 24.0h， 以81%的产率得到3-乙氧基螺[3.5]-2-壬烯-1-酮
  参考文献：
  名称：

  Efficient Synthesis of 3-Aminocyclobut-2-en-1-ones:  Squaramide Surrogates as Potent VLA-4 Antagonists

  摘要：

  [GRAPHICS]A novel series of uniquely functionalized 3-aminocyclobut-2-en-1-ones has been prepared by facile condensation of a variety of cyclobuta-1,3-diones with a phenylalanine-derived primary amine. These systems subsequently lend themselves to substitution at C-2 by reaction with a variety of electrophilic reagents including N-halosuccinimides, sulfenyl chlorides, and Eschenmoser's salt. Compounds from this novel series are potent antagonists of VLA-4.

  DOI：

  10.1021/ol034701n

文献信息

• Enantioselective Hydrofunctionalization of Cyclobutenones: Total Synthesis of <i>gem</i>‐Dimethylcyclobutane Natural Products
  作者：Shaowei Wang、Changxu Zhong、Yingchao Huang、Ping Lu

  DOI：10.1002/anie.202400515

  日期：——

  A sequential enantioselective reduction/trapping/cross-coupling reaction of cyclobutenones furnished an array of chiral trans-2,3-disubstituted-4,4-disubstituted cyclobutanones. The developed strategy was applied in the syntheses of several gem-dimethylcyclobutane-containing natural products, including (+)-β-caryophyllene, (−)-rumphellanones A−C, (−)-1β,9αH-5-linoleoyloxy-4,5-secocaryophyllen-4-one

  环丁烯酮的连续对映选择性还原/捕获/交叉偶联反应提供了一系列手性反式-2,3-二取代-4,4-二取代环丁酮。该策略应用于多种含偕二甲基环丁烷的天然产物的合成，包括(+)-β-石竹烯、(−)-rumphelanones A−C、(−)-1β,9α H -5-linoleoyloxy-4 ,5-仲石竹烯-4-酮和(-)-莱科维醛。
• Melaimi, Mohand; Parameswaran, Pattiyil; Donnadieu, Bruno, Angewandte Chemie - International Edition, 2009, vol. 48, p. 4792 - 4795
  作者：Melaimi, Mohand、Parameswaran, Pattiyil、Donnadieu, Bruno、Frenking, Gernot、Bertrand, Guy

  DOI：——

  日期：——
• Efficient Synthesis of 3-Aminocyclobut-2-en-1-ones:  Squaramide Surrogates as Potent VLA-4 Antagonists
  作者：Stephen Brand、Benjamin C. de Candole、Julien A. Brown

  DOI：10.1021/ol034701n

  日期：2003.6.1

  [GRAPHICS]A novel series of uniquely functionalized 3-aminocyclobut-2-en-1-ones has been prepared by facile condensation of a variety of cyclobuta-1,3-diones with a phenylalanine-derived primary amine. These systems subsequently lend themselves to substitution at C-2 by reaction with a variety of electrophilic reagents including N-halosuccinimides, sulfenyl chlorides, and Eschenmoser's salt. Compounds from this novel series are potent antagonists of VLA-4.