dimethyl 2-methylsulfanylmalonate | 24420-52-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dimethyl 2-methylsulfanylmalonate
• 英文别名: dimethyl methylthiomalonate；Dimethyl 2-methylsulfanylpropanedioate
• CAS: 24420-52-8
• 化学式: C₆H₁₀O₄S
• 分子量: 178.209
• InChiKey: KUIATCTWPZGWQH-UHFFFAOYSA-N

物化性质

• 沸点：
  150-155 °C(Press: 0.3 Torr)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl 2-methylsulfanylmalonate 在 silver(l) oxide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以93%的产率得到2,3-Bis-methoxycarbonyl-2,3-bis-methylsulfanyl-succinic acid dimethyl ester
  参考文献：
  名称：

  Couplage okydatif facile d'anions substitues captodativement

  摘要：

  DOI：

  10.1016/s0040-4039(00)98764-1
• 作为产物：
  描述：

  2-oxo-1-oxa-4-thiaspiro<4.5>decan-3-ylacetic acid 以84%的产率得到
  参考文献：
  名称：

  PELTER, A.;WARD, R. S.;COLLINS, P.;VENKATESWARLU, REVURU;KAY, I. T., J. CHEM. SOC. PERKIN TRANS., 1985, N 3, 587-594

  摘要：

  DOI：

文献信息

• Reactions between Nucleophiles and Sulfonium Ions Containing Electron-withdrawing Substituents
  作者：Haruo Matsuyama、HirosHi Minato、Michio Kobayashi

  DOI：10.1246/bcsj.48.3287

  日期：1975.11

  Sulfonium ions containing electron-withdrawing substituents are formed by the reactions between sulfonium ylides and suitable electrophiles. Reactivities of these sulfonium ions (MeR\overset+S–CX(CO2Me)2) with nucleophiles (Y−) are investigated. The products found are those of 1) C-attack (MeSR+YCX(CO2Me)2), 2) Me-attack (MeY+RSCX(CO2Me)2) and 3) R-attack (RY+MeSCX(CO2Me)2). When R is (+)-2-octyl and

  含有吸电子取代基的锍离子是由锍叶立德与合适的亲电子试剂反应形成的。研究了这些锍离子（MeR\overset+S–CX(CO2Me)2）与亲核试剂（Y-）的反应性。发现的产物是 1) C-攻击 (MeSR+YCX(CO2Me)2), 2) Me-攻击 (MeY+RSCX(CO2Me)2) 和 3) R-攻击 (RY+MeSCX(CO2Me)2) . 当 R 是 (+)-2-辛基并且 Y- 是溴离子时，发现的 RY 是具有 59% 光学纯度的 (-)-2-辛基溴。讨论了这些反应的机理。
• Reactivity of cyclooctene derived episulfonium ions toward nucleophiles and the course of sulfenyl halide addition to cyclooctene
  作者：A.S. Gybin、W.A. Smti、M.Z. Krimer、N.S. Zefirov、L.A. Novgorodtseva、N.K. Sadovaya

  DOI：10.1016/0040-4020(80)85049-6

  日期：1980.1

  The reactions of the stable S-methylepisutfonium ions derived from cis-cyclooctene with various nucleophiles were found to proceed mainly as the attack at a C atom of episulfonium ring in contrast to the previous data of Helmkamp et al.4 The course of the RSCI AdE-reaction with cyclooctene under the conditions of increased polarity corresponded to the formation of intermediates closely related to episulfonium

  与Helmkamp等人先前的数据相反，发现顺式-环辛烯衍生的稳定的S-甲基表氟鎓离子与各种亲核试剂的反应主要是由于对epi环的C原子的攻击而进行的。4在极性增加的条件下，RSCI Ad E与环辛烯的反应过程与形成与epi硫离子密切相关的中间体相对应。观察到2，4-二硝基苯并二烯硫基烯衍生物与顺式-环辛烯的反应发生了环1，5-氢化物移位。
• Capto-dative effects measured by azo decompositions
  作者：Zdenek Janousek、Jean-Luc Bougeois、Robert Merényi、Heinz G. Viehe、Alan E. Luedtke、Sara Gardner、Jack W. Timberlake

  DOI：10.1016/0040-4039(88)85167-0

  日期：1988.1

  The activation parameters determined for rates of decomposition of compounds 3a-d indicate a substantial difference in free energies of activation, approximately 6 , and can be explained on the basis of capto-dative stabilization of the incipient radicals.

  为化合物3a-d的分解速率而确定的活化参数表明活化自由能有实质性差异，约为6 ，并且可以基于初始自由基的capto-dative稳定性来解释。
• Reactions of dimethyl diazomalonate with divalent sulfides
  作者：Wataru Ando、Tomio Yagihara、Shigeru Tozune、Isamu Imai、Junji Suzuki、Tadao Toyama、Setuko Nakaido、Toshihiko Migita

  DOI：10.1021/jo00976a010

  日期：1972.6
• Chemistry of diazocarbonyl compounds: XXV. Comparative photochemistry of diazo compounds and sulfur ylides of the 1,3-dioxane-4,6-dione series
  作者：V. A. Nikolaev、V. V. Shevchenko、M. S. Platz、N. N. Khimich

  DOI：10.1134/s1070428006060029

  日期：2006.6

  Photochemical decomposition of 2,2-dialkyl-5-diazo-1,3-dioxane-4,6-diones in the presence of pyridine, methanol.. or dimethyl sulfide as carbene traps involves mainly the Wolff rearrangement which is likely to follow a concerted pattern, while the yield of the "carbene" products does not exceed 27-28%. No carbene intermediates are formed in the photolysis of the corresponding dioxo sulfonium ylides under analogous conditions, and the main photochemical process is 1,2-methyl shift (Stevens rearrangement), followed by photochemical transformations of the primary products according to the Norrish type 11 pattern.