4,4-(diacetyl)heptanedioic acid dimethyl ester | 13984-59-3

• 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: 4,4-(diacetyl)heptanedioic acid dimethyl ester
• 英文别名: Dimethyl 4,4-diacetylheptanedioate
• CAS: 13984-59-3
• 化学式: C₁₃H₂₀O₆
• 分子量: 272.298
• InChiKey: TWNIDYQXIMXRSZ-UHFFFAOYSA-N

物化性质

• 沸点：
  377.1±42.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  19
• 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：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  丙烯酸甲酯（MA） 、 乙酰丙酮 在 1-butyl-3-methylimidazolium hydroxide 作用下， 反应 2.0h， 以95%的产率得到4,4-(diacetyl)heptanedioic acid dimethyl ester
  参考文献：
  名称：

  离子液体作为催化剂和反应介质。任务特定的离子液体[bmIm] OH在将活性亚甲基化合物加成到共轭酮，羧酸酯和腈中的过程中产生了巨大的影响。

  摘要：

  [反应：见正文]在迈克尔加成反应中，已将一种特定任务的离子液体[bmIm] OH引入作为催化剂和反应介质。非常有趣的是，尽管以通常的方式添加α，β-不饱和酮，得到单加成产物，但这种离子液体始终驱动开链的1,3-二羰基化合物与α，β-不饱和酯和腈的反应。迈向双加成反应，仅需一步即可生产双加合物。

  DOI：

  10.1021/ol051004h

文献信息

• Ionic Liquid as Catalyst and Reaction Medium. The Dramatic Influence of a Task-Specific Ionic Liquid, [bmIm]OH, in Michael Addition of Active Methylene Compounds to Conjugated Ketones, Carboxylic Esters, and Nitriles
  作者：Brindaban C. Ranu、Subhash Banerjee

  DOI：10.1021/ol051004h

  日期：2005.7.1

  [reaction: see text] A task-specific ionic liquid, [bmIm]OH, has been introduced as a catalyst and as a reaction medium in Michael addition. Very interestingly, although the addition to alpha,beta-unsaturated ketones proceeds in the usual way, giving the monoaddition products, this ionic liquid always drives the reaction of open-chain 1,3-dicarbonyl compounds with alpha,beta-unsaturated esters and

  [反应：见正文]在迈克尔加成反应中，已将一种特定任务的离子液体[bmIm] OH引入作为催化剂和反应介质。非常有趣的是，尽管以通常的方式添加α，β-不饱和酮，得到单加成产物，但这种离子液体始终驱动开链的1,3-二羰基化合物与α，β-不饱和酯和腈的反应。迈向双加成反应，仅需一步即可生产双加合物。
• Ionic liquid as catalyst and solvent: the remarkable effect of a basic ionic liquid, [bmIm]OH on Michael addition and alkylation of active methylene compounds
  作者：Brindaban C. Ranu、Subhash Banerjee、Ranjan Jana

  DOI：10.1016/j.tet.2006.10.077

  日期：2007.1

  ketones, carboxylic esters and nitriles. It further catalyzes the addition of thiols to α,β-acetylenic ketones and alkylation of 1,3-dicarbonyl and -dicyano compounds. The Michael addition to α,β-unsaturated ketones proceeds in the usual way, giving the monoaddition products, whereas addition to α,β-unsaturated esters and nitriles leads exclusively to the bis-addition products. The α,β-acetylenic ketones

  碱性离子液体1-甲基-3-丁基咪唑鎓氢氧化物[bmIm] OH催化活性亚甲基化合物与共轭酮，羧酸酯和腈的迈克尔加成反应。它进一步催化将硫醇添加到α，β-炔基酮上，并使1,3-二羰基和-二氰基化合物烷基化。α，β-不饱和酮的迈克尔加成反应以通常的方式进行，得到单加成产物，而α，β-不饱和酯和腈的加成仅导致双加成产物。α，β-炔基酮与硫醇进行双重共轭加成，生成β-酮基1,3-二硫代衍生物。在烷基化反应中，无环的1，3-二酮被单烷基化，而环状酮在相同条件下进行二烷基化。所有这些反应均在没有任何有机溶剂的情况下进行。
• The base catalysed reaction of acetylacetone and acrylate esters
  作者：R Chong、PS Clezy

  DOI：10.1071/ch9670123

  日期：——

  In addition to 4-acetyl-5-oxohexanoate esters (I), the expected product of the Michael addition of acetylacetone to acrylates, three other products (III, IV, V) have been isolated from this reaction. The amount of sodium alkoxide used as catalyst in the reaction largely determines the proportions of the products obtained. Some aspects of the chemistry of these compounds are discussed.

  除了 4-乙酰基-5-氧代己酸酯（I）--丙烯酸酯与乙酰丙酮的迈克尔加成反应的预期产物 丙酮与丙烯酸酯的迈克尔加成反应的预期产物--4-乙酰基-5-氧代己酸酯（I）之外，还从该反应中分离出了另外三种产物（III、IV 和 V）。 从该反应中分离出了另外三种产物（III、IV、V）。反应中用作催化剂的氧化烷钠的量 催化剂的用量在很大程度上决定了所得产物的比例。 的比例。本文讨论了这些化合物化学性质的一些方面。
• Michael reactions promoted by η1-O-enolatoruthenium(II) complexes derived from Ru(cod)(cot), diphosphine, and dimethyl malonate
  作者：Salvador G. Alvarez、Sachi Hasegawa、Masafumi Hirano、Sanshiro Komiya

  DOI：10.1016/s0040-4039(98)01023-5

  日期：1998.7

  The Michael reaction of 1,3-dicarbonyls with alpha,beta-unsaturated esters and nitriles has been carried our very efficiently, under mild and neutral conditions, in the presence of a catalytic amount of trans-hydrido(eta(1)-O-enolato) ruthenium(II) complex (2), which is prepared from the reaction of Ru(cod)(cot) (1) (cod = cycloocta-1,5-diene; cot = cycloocta-1,3,5-triene) with dimethyl malonate in the presence of 1,2-bis(diphenylphosphino)ethane (dpe). (C) 1998 Elsevier Science Ltd. All rights reserved.
• Polymer-supported tertiaryphosphine (JJ–TPP) as a green and recyclable organocatalyst for α-addition of carbon nucleophiles to α,β-unsaturated compounds
  作者：Hai-Ling Liu、Huan-Feng Jiang

  DOI：10.1016/j.tet.2007.12.038

  日期：2008.2

  JJ - TPP has been demonstrated as an effective and reusable organocatalyst for alpha-addition of carbon nucleophiles to alpha,beta-unsaturated compounds under very mild and environmentally friendly conditions. Under the optimized reaction conditions, the desired addition products were obtained as only E isomer with 18 - 90% isolated yields. (c) 2007 Elsevier Ltd. All rights reserved.