(R)-(+)-2-<(4-methylphenyl)sulfinylmethyl>pyridine | 128949-52-0

• 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: (R)-(+)-2-<(4-methylphenyl)sulfinylmethyl>pyridine
• 英文别名: (R)-(+)-<2-pyridylmethyl p-tolyl sulfoxide>；(R)-(2-pyridyl)methyl 4-methylphenyl sulfoxide；(R)-(+)-2-pyridylmethyl p-tolyl sulfoxide；(R)-2-((p-tolylsulfinyl)methyl)pyridine；2-pyridylmethyl p-tolyl sulfoxide；2-{[(R)-4-methylbenzenesulfinyl]methyl}pyridine；2-[[(R)-(4-methylphenyl)sulfinyl]methyl]pyridine
• CAS: 128949-52-0
• 化学式: C₁₃H₁₃NOS
• 分子量: 231.318
• InChiKey: FLMKPKKHAAJSED-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  49.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(+)-2-<(4-methylphenyl)sulfinylmethyl>pyridine 在 zinc(II) iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 (1S)-1-tert-butyldimethylsiloxy-1-(2-pyridyl)propyl 4-methylpheny sulfide
  参考文献：
  名称：

  Kita, Yasuyuki; Shibata, Norio; Fukui, Seiji, Journal of the Chemical Society. Perkin transactions I, 1997, # 12, p. 1763 - 1767

  摘要：

  DOI：
• 作为产物：
  描述：

  2-pyridylmethyl p-tolyl sulfoxide 在 Escherichia coli DMSO reductase 作用下， 以 甲醇 、 aq. phosphate buffer 为溶剂， 反应 2.0h， 以11%的产率得到
  参考文献：
  名称：

  手性亚砜的酶动力学拆分–对映体互补方法†

  摘要：

  描述了一种新的用于制备手性亚砜的酶促测定方法，该方法与甲硫氨酸亚砜还原酶A（MsrA）的已知的（S）-对映异构体还原活性是对映体互补的。为此，我们利用了DMSO还原酶（DmsABC），该酶最近被我们发现在固定相大肠杆菌中高度上调。

  DOI：

  10.1039/c9cc05470g

文献信息

• Studies on the Stereoselective Methylation of α-Sulfinyl Carbanions Generated from Three Isomeric Pyridylmethyl<i>p</i>-Tolyl Sulfoxides and Benzyl 2-Pyridyl Sulfoxide
  作者：Naomichi Furukawa、Eri Hosono、Hisashi Fujihara、Satoshi Ogawa

  DOI：10.1246/bcsj.63.461

  日期：1990.2

  A high stereoselectivity in the methylation of 2-pyridylmethyl p-tolyl sulfoxide (2a) with lithium diisopropylamide and iodomethane was observed at low temperature. The chelation of Li+ by both the nitrogen atom in the pyridine ring and the sulfinyl oxygen atom in 2a promotes the stereoselectivity as compared with isomeric sulfoxides.

  在低温下观察到 2-吡啶基甲基对甲苯基亚砜 (2a) 与二异丙基氨基锂和碘甲烷的甲基化具有高立体选择性。与异构亚砜相比，吡啶环中的氮原子和 2a 中的亚磺酰基氧原子对 Li+ 的螯合提高了立体选择性。
• Enantioselective pummerer-type rearrangement by reaction of O-silylated ketene acetal with enantiopure α-substituted sulfoxides
  作者：Yasuyuki Kita、Norio Shibata、Seiji Fukui、Shigekazu Fujita

  DOI：10.1016/0040-4039(94)88372-6

  日期：1994.12

  Chiral non-racemic α-substituted sulfoxides were reacted with O-silylated ketene acetal in the presence of a catalytic amount of ZnI2 in THF to give chiral non-racemic α-siloxysulfides in >99% ee. This is the highest enantioselectivity reported to date for the Pummerer reaction.

  在催化量的ZnI 2在THF中的存在下，手性非外消旋α-取代的亚砜与O-甲硅烷基化的乙烯酮缩醛反应，得到ee> 99％的手性非外消旋α-甲硅烷氧基硫化物。这是迄今为止报道的Pummerer反应的最高对映选择性。
• Synthesis of new optically active sulfoxides with chelating properties
  作者：Kai - U. Baldenius、Henri B. Kagan

  DOI：10.1016/0957-4166(90)80010-v

  日期：1990.1

  2-pyridinylmethyl sulfoxides and β-imino sulfoxides was sought. The latter were obtained in tautomeric mixtures with their enamines by condensation of optically active β-keto sulfoxides with primary amines. 2-Pyridinylmethyl sulfoxides were synthesized by sulfinate substitution. Titanium catalysed oxidation gave good results for the synthesis of (+)-8-(methylsulfinyl)quinoline from the corresponding

  寻求获得对映体纯的2-吡啶基甲基亚砜和β-亚氨基亚砜。后者是通过将旋光性β-酮亚砜与伯胺缩合而与它们的烯胺以互变异构体混合物的形式获得的。通过亚磺酸酯取代合成2-吡啶基甲基亚砜。钛催化的氧化为由相应的硫化物合成（+）-8-（甲基亚磺酰基）喹啉提供了良好的结果。
• Role of Heterocycles on the Stereoselective Reactions of a-Sulfinyl Carbanions Using Optically Active 2-Pyridylmethyl p-Tolyl and 2-(N-Methylimidazolyl)methyl p-Toyl Sulfoxides with Aldehydes
  作者：Naomichi Furukawa、Takahiro Sagae、Satoshi Ogawa

  DOI：10.3987/com-91-5691

  日期：——

  Optically active 2-pyridylmethyl p-tolyl (1) and 2-(N-methylimidazolyl) methyl p-tolyl sulfoxides (2) were synthesized and the reactions of their chiral alpha-sulfinyl carbanions with aldehydes afforded stereoselectively the condensation products. The absolute configurations of the products were determined by x-ray crystallographic analysis and chemical reactions. The mechanism for the reactions is described.
• FURUKAWA, NAOMICHI;HOSONO, ERI;FUJIHARA, HISASHI;OGAWA, SATOSHI, BULL. CHEM. SOC. JAP., 63,(1990) N, C. 461-465
  作者：FURUKAWA, NAOMICHI、HOSONO, ERI、FUJIHARA, HISASHI、OGAWA, SATOSHI

  DOI：——

  日期：——