dimethyl 2-methyl-3-oxopropane-1,1-dicarboxylate | 51534-90-8

• 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: dimethyl 2-methyl-3-oxopropane-1,1-dicarboxylate
• 英文别名: (1-Formylethyl)malonsaeure-dimethylester；Dimethyl 2-(1-oxopropan-2-yl)propanedioate
• CAS: 51534-90-8
• 化学式: C₈H₁₂O₅
• 分子量: 188.18
• InChiKey: ZVJVIMYCRPQZJR-UHFFFAOYSA-N

物化性质

• 沸点：
  150 °C(Press: 0.01 Torr)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-propylidene malonic acid dimethyl ester 在 盐酸 、 甲醇 、 sodium iodide 作用下， 生成 dimethyl 2-methyl-3-oxopropane-1,1-dicarboxylate
  参考文献：
  名称：

  Electrochemically induced oxidative rearrangement of alkylidenemalonates

  摘要：

  Alkylidenemalonates capable of double bond migration being electrolyzed in methanol or ethanol in the presence of alkali metal halides in an undivided cell equipped with Fe cathode are transformed into 2-alkyl-3,3-dimethoxyalkane-1,1-dicarboxylates in 70-90% yield via electrochemically induced oxidative rearrangement. Acidification of the reaction mixture after the electrolysis leads to the formation of 2-alkyl-3-oxoalkane-1,1-dicarboxylates. In the case of isobutylidenemalonate, the electrolysis intermediate dimethyl 3,3-dimethyl-2-methoxycyclopropane-1,1-dicarboxylate was isolated in 70% yield. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00912-0

文献信息

• Asymmetric Synthesis of Succinic Semialdehyde Derivatives
  作者：José M. Lassaletta、Juan Vázquez、Auxiliadora Prieto、Rosario Fernández、Gerhard Raabe、Dieter Enders

  DOI：10.1021/jo026557+

  日期：2003.4.1

  (77-93%) after chromatographic separation. Direct, racemization-free BF(3).OEt(2)-catalyzed thiolysis of compounds 3 afforded dithioacetals 7. These compounds were transformed into malonates 8 and succinic semialdehyde derivatives 9 by Raney Nickel mediated desulfuration or decarboxylation, respectively.

  在MgI（2）存在下，将2-（二苯基甲氧基甲基）-1-亚甲基氨基吡咯烷1D亲核迈克尔加成到前手性脂肪族和芳香族亚烷基丙二酸酯中，从而以优异的收率和良好的选择性提供相应的迈克尔加合物3。在芳烃系列中，色谱分离后，以良好的收率（77-93％）分离出光学纯的（de> 98％）主要非对映异构体（S，S）-3。直接，无外消旋的BF（3）.OEt（2）催化的化合物3的硫解得到二硫缩醛7。这些化合物分别通过阮内镍介导的脱硫或脱羧作用分别转化为丙二酸酯8和琥珀酸半醛衍生物9。
• Asymmetric Michael addition of formaldehyde N,N-dialkylhydrazones to alkylidene malonates
  作者：Juan Vázquez、Auxiliadora Prieto、Rosario Fernández、Dieter Enders、José M. Lassaletta

  DOI：10.1039/b200209b

  日期：——

  Enantiopure formaldehyde N,N-dialkylhydrazones 1 smoothly react with prochiral alkylidene malonates 2 in the presence of MgI2 to afford the corresponding Michael adducts 3 in excellent yields and good diastereoselectivities; direct racemization-free BF3.OEt2-catalyzed thiolysis of the hydrazone C=N bond affords the corresponding dithioketals 7 in optically pure or enantiomerically enriched form.

  在MgI 2的存在下，对映纯甲醛N，N-二烷基hydr盐1与手性亚烷基丙二酸酯2平滑反应，以优异的收率和良好的非对映选择性提供相应的迈克尔加合物3。race C = N键的无外消旋的直接BF3.OEt2催化硫解得到了相应的光学纯或对映体富集形式的二硫缩酮7。
• Lidor, Rami; Shatzmiller, Shimon, Liebigs Annalen der Chemie, 1982, # 2, p. 226 - 230
  作者：Lidor, Rami、Shatzmiller, Shimon

  DOI：——

  日期：——
• Electrochemical transformation of alkylidenemalonates into 2-alkyl-3,3-dimethoxyalkane-1,1-dicarboxylates via rearrangement
  作者：Gennady I. Nikishin、Michail N. Elinson、Sergey K. Feducovich

  DOI：10.1016/s0040-4039(00)74890-8

  日期：1991.2

  Alkylidenemalonates capable of migration of a double bond being electrolyzed in methanol in the presence of alkali metal halides in an undivided cell are transformed into 2-alkyl-3,3-dimethoxyalkane-1,1-dicarboxylates, acidification of which leads to 2-alkyl-3-oxoalkane-1,1-dicarboxylates.
• Ketene thioacetal monoxides: A novel and versatile class of two-carbon michael receptors
  作者：J.L. Herrmann、G.R. Kieczykowski、R.F. Romanet、P.J. Wepplo、R.H. Schlessinger

  DOI：10.1016/s0040-4039(01)87317-2

  日期：——