α-methylsulfinylcyclohexanone | 67236-72-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚砜
• 英文名称: α-methylsulfinylcyclohexanone
• 英文别名: (+/-)-2-methylsulfinylcyclohexanone；(SS)-2-methylsulfinylcyclohexanone；2-methylsulfinylcyclohexan-1-one
• CAS: 67236-72-0
• 化学式: C₇H₁₂O₂S
• 分子量: 160.237
• InChiKey: SJAOPYFJCZLBQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲基硫代磺酸甲酯 、 α-methylsulfinylcyclohexanone 在 苄基三乙基氯化铵 potassium carbonate 作用下， 以 二氯甲烷 、 苯 为溶剂， 以75%的产率得到(+/-)-2-methylsulfanyl-2-methylsulfinylcyclohexanone
  参考文献：
  名称：

  Phase Transfer Catalysis (PTC) Sulfanylation of Some 2-Methylsulfinyl-Cyclanones

  摘要：

  The sulfanylation reactions of 2-methylsulfinylated cyclopentanone, 1-indanone, and cyclohexanone by a PTC procedure are reported and the yields and diastereoselectivity compared to those obtained by the homogeneousphase method. The stability of the sulfanylated methylsulfinyl derivatives at room temperature versus the instability of the p-tolylsulfinyl derivatives is also reported.

  DOI：

  10.1021/jo048751x
• 作为产物：
  描述：

  2-(甲硫基)环己酮 在 sodium periodate 作用下， 以70%的产率得到α-methylsulfinylcyclohexanone
  参考文献：
  名称：

  Phase Transfer Catalysis (PTC) Sulfanylation of Some 2-Methylsulfinyl-Cyclanones

  摘要：

  The sulfanylation reactions of 2-methylsulfinylated cyclopentanone, 1-indanone, and cyclohexanone by a PTC procedure are reported and the yields and diastereoselectivity compared to those obtained by the homogeneousphase method. The stability of the sulfanylated methylsulfinyl derivatives at room temperature versus the instability of the p-tolylsulfinyl derivatives is also reported.

  DOI：

  10.1021/jo048751x

文献信息

• Asymmetric phase-transfer catalytic sulfanylation of some 2-methylsulfinyl cyclanones. Modeling of the stereochemical course of the aldol reaction of (SS,2S)-2-methylsulfinyl-2-methylsulfanylcyclohexanone
  作者：Alessandro Rodrigues、Blanka Wladislaw、Claudio Di Vitta、José Eduardo Pandini Cardoso Filho、Liliana Marzorati、Mauro Alves Bueno、Paulo Roberto Olivato

  DOI：10.1016/j.tetlet.2010.08.010

  日期：2010.10

  2-methylsulfinyl cyclanones under phase-transfer catalysis using the chiral catalyst QUIBEC instead of TEBA. The optically pure (SS,2S)-2-methylsulfinyl-2-methylsulfanylcyclohexanone thus prepared reacts with ethyl acetate lithium enolate affording, after hydrolysis, (R)-2-[(ethoxycarbonyl)methyl]-2-hydroxycyclohexanone in 60% ee. Density functional theory calculations (at the B3LYP/6-311++G(d,p) level)

  使用手性催化剂QUIBEC代替TEBA，在相转移催化下，某些2-甲基亚磺酰基环戊酮的磺酰化反应会增加非对映异构体过量。如此制备的光学纯的（S S，2 S）-2-甲基亚磺酰基-2-甲基硫烷基环己酮与乙酸乙酯烯醇锂反应，水解后得到60％的（R）-2-[（乙氧基羰基）甲基] -2-羟基环己酮ee。密度泛函理论计算（在B3LYP / 6-311 ++ G（d，p）水平）可以成功地解释此结果的起源，因为亲核试剂对分子中最稳定构象异构体的羰基具有动力学上的轴向攻击。环烷酮，其中CH 3 SO和CH 3S组分别位于赤道和轴向位置。
• The Preparation of β-Oxo Sulfoxides from Sulfinyl Chlorides and Trimethylsilyl Enol Ethers
  作者：Nicholas A. Meanwell、Carl R. Johnson

  DOI：10.1055/s-1982-29780

  日期：——
• Kano, Shinzo; Shibuya, Shiroshi; Yuasa, Yoko, Journal of Heterocyclic Chemistry, 1980, vol. 17, # 6, p. 1559 - 1561
  作者：Kano, Shinzo、Shibuya, Shiroshi、Yuasa, Yoko

  DOI：——

  日期：——
• Glahsl, Gudrun; Herrmann, Rudolf, Journal of the Chemical Society. Perkin transactions I, 1988, p. 1753 - 1758
  作者：Glahsl, Gudrun、Herrmann, Rudolf

  DOI：——

  日期：——
• KANO SHINZO; SHIBUYA SHIROSHI; YUASA YOKO, J. HETEROCYCL. CHEM., 1980, 17, NO 7, 1559-1561
  作者：KANO SHINZO、 SHIBUYA SHIROSHI、 YUASA YOKO

  DOI：——

  日期：——