仲-丁基3-甲基-2-丁烯酸酯 | 109892-46-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 仲-丁基3-甲基-2-丁烯酸酯
• 英文名称: 3-methyl-crotonic acid sec-butyl ester
• 英文别名: 3-Methyl-crotonsaeure-sec-butylester；Butan-2-yl 3-methylbut-2-enoate
• CAS: 109892-46-8
• 化学式: C₉H₁₆O₂
• mdl: MFCD09701467
• 分子量: 156.225
• InChiKey: XIUGHTPAQPTLFH-UHFFFAOYSA-N

物化性质

• 沸点：
  187.8±9.0 °C(Predicted)
• 密度：
  0.895±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2916190090

反应信息

• 作为反应物：
  描述：

  仲-丁基3-甲基-2-丁烯酸酯 在 lithium aluminium tetrahydride 、 三甲基氯硅烷 、 三乙胺 、 copper(l) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Potent Anandamide Analogs:  The Effect of Changing the Length and Branching of the End Pentyl Chain

  摘要：

  To examine the effect of changing the length and branching of the end pentyl chain (C5H11) of anandamide (AN), various analogs 1a-h and 2a-f were synthesized from either the known aldehyde ester 6a or from the alcohol 6b and tested for their pharmacological activity. A reproducible procedure was developed for the conversion of arachidonic acid to 6a or 6b in gram quantities (overall yield 15%). The appropriate tetraene esters 7 were prepared by carrying out a Wittig reaction, between 6a and the ylide generated from the phosphonium salt of the appropriate alkyl halide or between the ylide of 6d (prepared from 6a --> 6b --> 6c --> 6d) and the appropriate alkyl aldehydes. They were then hydrolyzed to the corresponding acids and transformed into AN analogs 1 via their acid chlorides then treated with excess ethanolamine. alpha-Alkylation of esters 7 gave compounds 8 which were hydrolyzed to the corresponding acids. These acids via their acid chlorides and subsequent treatment with excess fluoroethylamine gave the target compounds 2. In this way analogs 1e and 2a-c were synthesized from 6d while all the remaining analogs were prepared from 6a. In order to assess the optimal length of the alkyl terminus, analogs 1a-d were prepared and showed moderately high affinities (18-55 nM). However analogs 1a-c failed to produce significant pharmacological effects at doses up to 30 mg/kg. Analog 1d was found to be a weak partial agonist. The reason for the lack of activity in 1a-c is presently not clear. Like the THCs, the branching of the end pentyl chain in AN (1e-h) increased potency both in in vitro and in vivo activities; the dimethylheptyl (DMH) analog 1e was the most potent in the series. Similar alkyl substitutions were carried out in the fluoro-2-methylanandamide series (2a-f), and all of these analogs had high receptor affinities (1-14 nM), the DMH analog 2a being the most potent. With a few exceptions they showed robust pharmacological effects, and AN-like profiles, It was shown that the SAR of the end pentyl chain in AN is very similar to that of THCs. However, the magnitude of enhanced potency observed when the side chain of THC was changed from straight to branched was not observed when the end chain of AN was similarly changed.

  DOI：

  10.1021/jm970212f
• 作为产物：
  描述：

  3,3-二甲基丙烯酸 、 仲丁醇 在 硫酸 、 苯 作用下， 生成 仲-丁基3-甲基-2-丁烯酸酯
  参考文献：
  名称：

  Munch-Petersen, Acta Chemica Scandinavica (1947), 1958, vol. 12, p. 967,969

  摘要：

  DOI：

文献信息

• Process for Conducting an Organic Reaction in Ionic Liquids
  申请人：Bourgeois Daniel Martin

  公开号：US20110152566A1

  公开（公告）日：2011-06-23

  The present disclosure describes processes for producing cyclohexenes using Lewis acidic ionic liquids comprising the steps of providing to a reactor an α,β-unsaturated carbonyl dienophile, providing to the reactor a 1,3-diene, providing a Lewis acidic ionic liquid to the reactor; and reacting the α,β-unsaturated carbonyl dienophile with 1,3-diene to form a substituted cyclohexene product. The α,β-unsaturated carbonyl dienophile can be mesityl oxide, the 1,3-diene can be piperylene; and the Lewis acidic ionic liquid can be AlCl 3 :[C 2 mim]Cl; AlCl 3 :[C 8 mim]Cl; or mixtures thereof.

  本公开描述了使用含有Lewis酸性离子液体的方法生产环己烯的过程，包括向反应器提供α，β-不饱和羰基二烯亲受体，向反应器提供1,3-二烯，向反应器提供Lewis酸性离子液体；并将α，β-不饱和羰基二烯亲受体与1,3-二烯反应以形成取代环己烯产物。α，β-不饱和羰基二烯亲受体可以是甲苯酮氧，1,3-二烯可以是戊二烯；Lewis酸性离子液体可以是AlCl3:[C2mim]Cl； :[C8mim]Cl；或它们的混合物。
• Munch-Petersen, Acta Chemica Scandinavica (1947), 1958, vol. 12, p. 2007,2009
  作者：Munch-Petersen

  DOI：——

  日期：——
• Conia,J.-M.; Leriverend,M.-L., Bulletin de la Societe Chimique de France, 1970, p. 2981 - 2991
  作者：Conia,J.-M.、Leriverend,M.-L.

  DOI：——

  日期：——
• FRAGMENTATION-RECOMBINATION NAZAROV CYCLIZATION: 3,4-DIMETHYLCYCLOPENT-2-EN-1-ONE
  作者：Schwartz, Keith D.、White, James D.、Tosaki, Shin-ya、Shibasaki, Masakatsu

  DOI：10.15227/orgsyn.083.0049

  日期：——
• MITTEL ZUM FÄRBEN VON KERATINHALTIGEN FASERN ENTHALTEND MINDESTENS EIN OXOCYCLOPENTENDERIVAT
  申请人：Henkel Kommanditgesellschaft auf Aktien

  公开号：EP1311231A1

  公开（公告）日：2003-05-21