3-isopropyl-4-methyl-2-pentenoic acid ethyl ester | 21046-03-7

• 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: 3-isopropyl-4-methyl-2-pentenoic acid ethyl ester
• 英文别名: 4-Methyl-3-(1-methylethyl)-2-pentenoic acid ethyl ester；3-Isopropyl-4-methyl-penten-(2)-saeureethylester；Ethyl 4-methyl-3-(1-methylethyl)-2-pentenoate；Ethyl 3-isopropyl-4-methylpent-2-enoate；ethyl 4-methyl-3-propan-2-ylpent-2-enoate
• CAS: 21046-03-7
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: SHUMILKEZSWTMJ-UHFFFAOYSA-N

物化性质

• 沸点：
  224.3±9.0 °C(Predicted)
• 密度：
  0.886±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• 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

反应信息

• 作为反应物：
  描述：

  3-isopropyl-4-methyl-2-pentenoic acid ethyl ester 在 正丁基锂 、 三苯基甲烷 、 三甲基铝 、 1,2-环氧辛烷 、 天然维生素E 作用下， 以 various solvent(s) 为溶剂， 反应 8.25h， 生成 (Z)-5-Ethylidene-4,4-dimethyl-3-(1-methylethyl)-2-cyclopenten-1-one
  参考文献：
  名称：

  Enynones in Organic Synthesis. 6. Synthesis of Spirocyclic Methylenecyclopentenones and Analogs of the Methylenomycin Class of Antibiotics. Mechanism of Phenol Catalysis

  摘要：

  Spirocyclic methylenecyclopentenones of general structure 18 were prepared in a single step from bis-acetylenic alcohols 29 by a process involving initial oxy-Cope rearrangement to afford (Z)-enynones 30-Z followed by electrocyclic ring closure. Mechanistic studies indicate that the initial step leading from 30-Z to 18 is a thermal 1,5-prototropic shift to afford dienols which can cyclize by a symmetry-allowed (pi(4)s + sigma(2)s + pi(2)a) process. This last step is catalyzed by certain phenols having low oxidation potentials, most likely by a mechanism involving single electron transfer. Dramatic rate enhancements were also observed for the cyclization of simple enynones 37 to methylenecyclopentenones 39 upon catalysis with either a-tocopherol (vitamin E, 40) or tert-butylcatechol(41). Further enhancements in both rate and yield were obtained under conditions of photoassisted single electron transfer (PET), which afforded 39 in yields of 80-98%.

  DOI：

  10.1021/jo00097a035
• 作为产物：
  描述：

  磷酰基乙酸三乙酯 、 2,4-二甲基-3-戊酮 在 sodium hydride 作用下， 生成 3-isopropyl-4-methyl-2-pentenoic acid ethyl ester
  参考文献：
  名称：

  Photochemistry of .alpha.,.beta.-unsaturated esters. IV. Cyclopropyl conjugation in olefinic esters. Conformational effects on ultraviolet absorption

  摘要：

  DOI：

  10.1021/ja01016a029

文献信息

• Die Gasphasen-Flussthermolyse von 1-Isobutenyl- und 2-Methylphenyl-alkinyl-ketonen. Eine Synthese von Methylenomycin B
  作者：Manuel Koller、Martin Karpf、Andr� S. Dreiding

  DOI：10.1002/hlca.19860690306

  日期：1986.5.7

  The Gas-Flow Thermolysis of 1-Isobutenyl Alkynyl and 2-Methylphenyl Alkynyl Ketones. Synthesis of Methylenomycin B

  1-异丁烯基炔基和2-甲基苯基炔基酮的气流热解。甲基霉素B的合成
• Antihypercholesterolemic alkylene compounds
  申请人：Bristol-Myers

  公开号：US05011947A1

  公开（公告）日：1991-04-30

  Compounds of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each are independently hydrogen, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or trifluoromethyl; R is C.sub.1-7 alkyl, C.sub.3-6 cycloalkyl, fluoromethyl, difluoromethyl, trifluoromethyl; A is ##STR2## R.sup.5 is hydrogen, a hydrolyzable ester group or a cation to form a non-toxic pharmaceutically acceptable salt, are novel antihypercholesterolemic agents which inhibit cholesterol biosynthesis. Intermediates and processes for their preparation are disclosed.

  该公式化合物的化合物##STR1##其中R.sup.1、R.sup.2、R.sup.3和R.sup.4分别独立地是氢、卤素、C.sub.1-4烷基、C.sub.1-4烷氧基或三氟甲基；R是C.sub.1-7烷基、C.sub.3-6环烷基、氟甲基、二氟甲基、三氟甲基；A是##STR2##R.sup.5是氢、可水解酯基或阳离子，形成无毒的药用可接受盐，是抑制胆固醇生物合成的新型抗高胆固醇药物。公开了其制备的中间体和过程。
• RATHKE, MICHAEL W.;BOUHLEL, EZZEDDINE, SYNTH. COMMUN., 20,(1990) N, C. 869-875
  作者：RATHKE, MICHAEL W.、BOUHLEL, EZZEDDINE

  DOI：——

  日期：——
• US5011947A
  申请人：——

  公开号：US5011947A

  公开（公告）日：1991-04-30
• Photochemistry of .alpha.,.beta.-unsaturated esters. IV. Cyclopropyl conjugation in olefinic esters. Conformational effects on ultraviolet absorption
  作者：Margaret J. Jorgenson、Teresa Leung

  DOI：10.1021/ja01016a029

  日期：1968.7