1-(4-dimethylaminophenyl)-2-(dimethyl-λ4-sulfanylidene)ethanone | 1259377-11-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-dimethylaminophenyl)-2-(dimethyl-λ4-sulfanylidene)ethanone
• 英文别名: 1-[4-(Dimethylamino)phenyl]-2-(dimethyl-lambda4-sulfanylidene)ethanone；1-[4-(dimethylamino)phenyl]-2-(dimethyl-λ4-sulfanylidene)ethanone
• CAS: 1259377-11-1
• 化学式: C₁₂H₁₇NOS
• 分子量: 223.339
• InChiKey: OLIUEZHTWQEOOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  39.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-dimethylaminophenyl)-2-(dimethyl-λ4-sulfanylidene)ethanone 、 反丁烯二腈 以 二甲基亚砜 为溶剂， 反应 0.08h， 以62%的产率得到3-(4-(dimethylamino)benzoyl)cyclopropane-1,2-dicarbonitrile
  参考文献：
  名称：

  1,2-二取代乙烯的亲电性

  摘要：

  在 DMSO 中，在 20 °C 下研究了马来酸酐、N-甲基马来酰亚胺、富马腈、富马酸二乙酯和马来酸二乙酯与吡啶鎓和锍叶立德的反应动力学。发现所有反应都遵循二阶速率定律，可以通过线性自由能关系 log k2 (20 °C) = sN(N + E) 来描述，其中 N 和 sN 是溶剂依赖性亲核试剂 -特定参数，E 是亲电试剂特定参数。所研究的受体取代烯烃的亲电性参数 E 源自 (log k2)/sN 与 N 的线性相关性，范围从 –19.8 到 –11.1。

  DOI：

  10.1002/ejoc.201301779

文献信息

• Scope and Limitations of Cyclopropanations with Sulfur Ylides
  作者：Roland Appel、Nicolai Hartmann、Herbert Mayr

  DOI：10.1021/ja1084749

  日期：2010.12.22

  The rates of the reactions of the stabilized and semistabilized sulfur ylides 1a-g with benzhydrylium ions (2a-e) and Michael acceptors (2f-v) have been determined by UV-vis spectroscopy in DMSO at 20 degrees C. The second-order rate constants (log k(2)) of these reactions correlate linearly with the electrophilicity parameters E of the electrophiles 2 as required by the correlation log k(2) = s(N + E), which allowed us to calculate the nucleophile-specific parameters N and s for the sulfur ylides 1a-g. The rate constants for the cyclopropanation reactions of sulfur ylides with Michael acceptors lie on the same correlation line as the rate constants for the reactions of sulfur ylides with carbocations. This observation is in line with a stepwise mechanism for the cyclopropanation reactions in which the first step, nucleophilic attack of the sulfur ylides at the Michael acceptors, is rate determining. As the few known pK(aH) values for sulfur ylides correlate poorly with their nucleophilic reactivities, the data reported in this work provide the first quantitative approach to sulfur ylide reactivity.
• Electrophilicities of 1,2-Disubstituted Ethylenes
  作者：Dominik S. Allgäuer、Herbert Mayr

  DOI：10.1002/ejoc.201301779

  日期：2014.5

  described by the linear free energy relationship log k2 (20 °C) = sN(N + E), where N and sN are solvent-dependent nucleophile-specific parameters, and E is an electrophile-specific parameter. The electrophilicity parameters E of the investigated acceptor-substituted alkenes were derived from the linear correlations of (log k2)/sN vs. N, and range from –19.8 to –11.1.

  在 DMSO 中，在 20 °C 下研究了马来酸酐、N-甲基马来酰亚胺、富马腈、富马酸二乙酯和马来酸二乙酯与吡啶鎓和锍叶立德的反应动力学。发现所有反应都遵循二阶速率定律，可以通过线性自由能关系 log k2 (20 °C) = sN(N + E) 来描述，其中 N 和 sN 是溶剂依赖性亲核试剂 -特定参数，E 是亲电试剂特定参数。所研究的受体取代烯烃的亲电性参数 E 源自 (log k2)/sN 与 N 的线性相关性，范围从 –19.8 到 –11.1。