2-But-3-enyl-2-(3-methyl-buta-1,2-dienyl)-malonic acid dimethyl ester | 474383-73-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-But-3-enyl-2-(3-methyl-buta-1,2-dienyl)-malonic acid dimethyl ester
• CAS: 474383-73-8
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: UAYPNTWFUPLJOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-But-3-enyl-2-(3-methyl-buta-1,2-dienyl)-malonic acid dimethyl ester 在 gold(III) chloride 、 silver hexafluoroantimonate 、 溶剂黄146 作用下， 以96%的产率得到methyl 3-(but-3-enyl)-3,6-dihydro-6,6-dimethyl-2-oxo-2H-pyran-3-carboxylate
  参考文献：
  名称：

  Gold-Catalyzed Cyclization of Allene-Substituted Malonate Esters:  Synthesis of β,γ-Unsaturated δ-Lactones

  摘要：

  An efficient method for the preparation of beta,gamma-unsaturated delta-lactones has been developed. The starting materials for the synthesis of these compounds are allene-substituted malonates which undergo gold-catalyzed cyclization by means of nucleophilic attack of the ester moiety on the allene. It is worth mentioning that this is the first example where an ester group attacks as a nucleophile in a gold-catalyzed transformation of allenes.

  DOI：

  10.1021/ol070793v
• 作为产物：
  描述：

  2-(3-Bromo-but-3-enyl)-malonic acid dimethyl ester 在 偶氮二异丁腈 、 三正丁基氢锡 、 甲铝双(2,6-二叔丁基-4-苯甲醚) 、 sodium hydride 作用下， 以 苯 为溶剂， 生成 2-But-3-enyl-2-(3-methyl-buta-1,2-dienyl)-malonic acid dimethyl ester
  参考文献：
  名称：

  Radical β-Elimination of a Sulfinyl Group to Afford Allenes

  摘要：

  DOI：

  10.1002/1099-0690(200206)2002:11<1776::aid-ejoc1776>3.0.co;2-6

文献信息

• Radical β-Elimination of a Sulfinyl Group to Afford Allenes
  作者：Virginie Mouriès、Bénédicte Delouvrié、Emmanuel Lacôte、Louis Fensterbank、Max Malacria

  DOI：10.1002/1099-0690(200206)2002:11<1776::aid-ejoc1776>3.0.co;2-6

  日期：2002.6
• Gold-Catalyzed Cyclization of Allene-Substituted Malonate Esters:  Synthesis of <i>β</i>,<i>γ</i>-Unsaturated <i>δ</i>-Lactones
  作者：Julio Piera、Patrik Krumlinde、Dirk Strübing、Jan-E. Bäckvall

  DOI：10.1021/ol070793v

  日期：2007.5.1

  An efficient method for the preparation of beta,gamma-unsaturated delta-lactones has been developed. The starting materials for the synthesis of these compounds are allene-substituted malonates which undergo gold-catalyzed cyclization by means of nucleophilic attack of the ester moiety on the allene. It is worth mentioning that this is the first example where an ester group attacks as a nucleophile in a gold-catalyzed transformation of allenes.