2-(N,N-Dimethylamino)phenyl methyl sulfoxide

• 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: 2-(N,N-Dimethylamino)phenyl methyl sulfoxide
• 英文别名: o-(N,N-dimethylamino)phenyl methyl sulfoxide；N,N-dimethyl-2-methylsulfinylaniline
• 化学式: C₉H₁₃NOS
• 分子量: 183.274
• InChiKey: MVMHGDVRJCXTQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  2
• 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：

  2-(N,N-Dimethylamino)phenyl methyl sulfoxide 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.17h， 生成 (Z)-2-phenyl-1-[2-(N,N-dimethylamino)phenylsulfinyl]ethene
  参考文献：
  名称：

  通过Heck反应高度立体选择性地合成三取代的α，β-不饱和亚砜。

  摘要：

  DOI：

  10.1021/jo010255a

文献信息

• Asymmetric Pauson-Khand Cyclizations of 1-Sulfinylenynes
  作者：Juan Carlos Carretero、Javier Adrio

  DOI：10.1055/s-2001-17511

  日期：——

  The use of sulfoxides as chiral auxiliaries in intramolecular Pauson-Khand (PK) reactions is described. In particular, the tert-butylsulfinyl group acts as a very efficient chiral auxiliary in intramolecular PK reactions of 1-sulfinyl-1,6-enynes. As the starting enynes are readily available in optically pure form and the final desulfinylation step is high yielding, this procedure constitutes an efficient alternative to the synthesis of enantiomerically pure bicyclo[3.3.0]oct-1-en-3-ones.

  描述了亚磺酰胺作为手性辅助剂在分子内Pauson-Khand（PK）反应中的应用。特别是，叔丁基亚磺酰基团在1-亚磺酰基-1,6-炔烃的分子内PK反应中作为非常有效的手性辅助剂。由于起始的炔烃易于获得光学纯的形式，而且最终的去亚磺酰化步骤产率很高，因而该方法为合成对映体纯的双环[3.3.0]八烯-1-酮提供了一种高效的替代方案。
• Unusual mechanisms in Claisen rearrangements: an ionic fragmentation leading to a <i>meta</i>-selective rearrangement
  作者：Boris Maryasin、Dainis Kaldre、Renan Galaverna、Immo Klose、Stefan Ruider、Martina Drescher、Hanspeter Kählig、Leticia González、Marcos N. Eberlin、Igor D. Jurberg、Nuno Maulide

  DOI：10.1039/c7sc04736c

  日期：——

  A mechanistic investigation of the acid-catalysed redox-neutral oxoarylation reaction of ynamides using electrospray ionisation mass-spectrometry (ESI-MS) and quantum chemical calculations (DFT and MP2) is presented. This study reveals the diversity of pathways and products available from an otherwise deceptively simple-looking, classical transformation: fragmentation, an unusual meta-arylation and

  提出了使用电喷雾电离质谱（ESI-MS）和量子化学计算（DFT和MP2）进行的酸催化的酰胺类氧化还原-中性羰基化反应的机理研究。这项研究揭示了从看似简单的经典转化中可以得到的途径和产物的多样性：裂解，不寻常的间位芳构化和竞争的α-羰基阳离子途径是ESI-MS和机理实验揭示的一些替代方法。详细的计算可以解释观察到的趋势并使结果合理化。
• The 2-(<i>N</i>,<i>N</i>-Dimethylamino)phenylsulfinyl Group as an Efficient Chiral Auxiliary in Intramolecular Heck Reactions
  作者：Nuria Díaz Buezo、Olga García Mancheño、Juan C. Carretero

  DOI：10.1021/ol005779w

  日期：2000.5.1

  reactivity, and stereochemical behavior of differently substituted iodoalkenyl alpha,beta-unsaturated sulfoxides in intramolecular Heck reaction is described. Particularly, the 2-(N,N-dimethylamino)phenylsulfinyl group is demonstrated to be an effective chiral auxiliary for the intramolecular Heck reaction of 2-iodo-1,6-(or 1,7)dienes. A desulfinylation sequence removes the auxiliary and yields cyclic

  描述了不同取代的碘烯基α，β-不饱和亚砜在分子内Heck反应中的合成，反应性和立体化学行为。特别地，证明2-（N，N-二甲基氨基）苯基亚磺酰基是2-碘-1，6-（或1，7）二烯的分子内Heck反应的有效手性助剂。脱亚磺酰化序列除去助剂并产生高对映体纯度的环状化合物。
• Sulfoxides as Stereochemical Controllers in Intermolecular Heck Reactions
  作者：Nuria Díaz Buezo、Juan Carlos de la Rosa、Julián Priego、Inés Alonso、Juan Carlos Carretero

  DOI：10.1002/1521-3765(20010917)7:18<3890::aid-chem3890>3.0.co;2-y

  日期：2001.9.17

  The study of a variety of substituted sulfoxides as chiral auxiliaries in intermolecular Heck reactions of sulfinyldihydrofurans and sulfinylcyclopentenes with different iodoarenes is reported. In the presence of [Pd(OAc)(2)]/Ag2CO3 and a bidentate phosphine ligand, synthetically useful yields and asymmetric inductions were obtained. By far the best diastereoselectivities were obtained by the use of the palladium-coordinating o-(N,N-dimethylamino)phenylsulfinyl group. By final removal of the chiral auxiliary, these sulfoxide-stereocontrolled asymmetric Heck processes were applied to the enantioselective synthesis of 1-aryl-substituted and 1,3-diaryl-substituted dihydrofurans and cyclopentenes.
• Highly Stereoselective Synthesis of Trisubstituted α,β-Unsaturated Sulfoxides by Heck Reaction
  作者：Inés Alonso、Juan C. Carretero

  DOI：10.1021/jo010255a

  日期：2001.6.1