2-(4-Methylpent-4-enyl)malonic acid ethyl ester | 25118-22-3

• 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-(4-Methylpent-4-enyl)malonic acid ethyl ester
• 英文别名: diethyl 2-(4-methylpent-4-en-1-yl)malonate；Diethyl 2-(4-methylpent-4-enyl)propanedioate
• CAS: 25118-22-3
• 化学式: C₁₃H₂₂O₄
• 分子量: 242.315
• InChiKey: XEIDZAFGPMNECJ-UHFFFAOYSA-N

物化性质

• 沸点：
  298.2±33.0 °C(Predicted)
• 密度：
  0.987±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 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-(4-Methylpent-4-enyl)malonic acid ethyl ester 在 氢氧化钾 、 二叔丁基过氧化物 作用下， 以 乙醇 、 环己烷 为溶剂， 生成 3-甲基环己烷-1,1-二羧酸
  参考文献：
  名称：

  Julia,M.; Maumy,M., Bulletin de la Societe Chimique de France, 1969, p. 2415 - 2427

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲基-4-戊烯酸乙酯 在 lithium aluminium tetrahydride 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 15.75h， 生成 2-(4-Methylpent-4-enyl)malonic acid ethyl ester
  参考文献：
  名称：

  Radical Cyclization of Epoxy Vinyl- and Allylsulfones Promoted by Titanocene Chloride

  摘要：

  A titanocene-mediated intramolecular radical addition of different epoxy vinyl- and allylsulfones has been achieved. Five- and Six-membered ring products were obtained in good to excellent yields in the presence of both 2.2 and 0.2 equiv of Cp2TiCl. A novel double-activation strategy allowed us to achieve small-size rings such as cyclobutanes and cyclopropanes.

  DOI：

  10.1021/acs.joc.5b00206

文献信息

• Facile Synthesis of Aliphatic Esters, Malonates and Phenylsulfonyl Esters Using Copper-Catalyzed Addition of Methallyl Grignard Reagent to Activated Cyclopropanes
  作者：Igor Prowotorow、Jerzy Wicha、Koichi Mikami

  DOI：10.1055/s-2001-9751

  日期：——

  Copper-mediated conjugate addition of allylic Grignard reagents to activated cyclopropane derivatives was studied. Unsaturated esters, malonates and phenylsulfonyl esters 2a-d were synthesized from the respective cyclopropanes 1a-d and methallylmagnesium chloride.

  研究了铜介导的烯丙基格氏试剂与活化环丙烷衍生物的共轭加成。不饱和酯、丙二酸酯和苯磺酰基酯 2a-d 分别由环丙烷 1a-d 和甲基烯丙基氯化镁合成。
• Ring Opening of Methylenecycloalkenes via the C−C Bond Cleavage
  作者：David Nečas、Martin Kotora

  DOI：10.1021/ol801728f

  日期：2008.11.20

  3-Methylenecycloalkene-1,1-dicarboxylates underwent facile ring opening via the cleavage of the unactivated C-C bond to yield aliphatic alkenes. The reaction (intramolecular deallylation) was catalyzed by "Ni-H" species generated in situ from a NiX2(phosphine) n/R3Al mixture and proceeded under ambient conditions. In addition, the skeletal rearrangement of a diene could be carried out by a one-pot

  3-亚甲基环烯烃-1,1-二羧酸酯通过未活化的CC键的裂解而容易地开环，从而生成脂肪族烯烃。该反应（分子内脱醛）由NiX2（膦）n / R3Al混合物原位产生的“ Ni-H”物质催化，并在环境条件下进行。另外，二烯的骨架重排可通过一锅环异构化/去芳基化序列进行。
• US4362670A
  申请人：——

  公开号：US4362670A

  公开（公告）日：1982-12-07
• Radical Cyclization of Epoxy Vinyl- and Allylsulfones Promoted by Titanocene Chloride
  作者：A. Fernández-Mateos、S. Encinas Madrazo、P. Herrero Teijón、R. Rubio González

  DOI：10.1021/acs.joc.5b00206

  日期：2015.5.1

  A titanocene-mediated intramolecular radical addition of different epoxy vinyl- and allylsulfones has been achieved. Five- and Six-membered ring products were obtained in good to excellent yields in the presence of both 2.2 and 0.2 equiv of Cp2TiCl. A novel double-activation strategy allowed us to achieve small-size rings such as cyclobutanes and cyclopropanes.
• Julia,M.; Maumy,M., Bulletin de la Societe Chimique de France, 1969, p. 2415 - 2427
  作者：Julia,M.、Maumy,M.

  DOI：——

  日期：——