2-Methylsulfonylethynylcyclohexane | 130612-94-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: 2-Methylsulfonylethynylcyclohexane
• CAS: 130612-94-1
• 化学式: C₉H₁₄O₂S
• 分子量: 186.275
• InChiKey: VRNFWTSIHMOYAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  297.8±23.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Methylsulfonylethynylcyclohexane 在 2,6-二氯吡啶N-氧化物 、 JohnPhosAuNTf₂ 、 氟化氢吡啶 作用下， 以90%的产率得到
  参考文献：
  名称：

  烷基炔砜在不同的区域和立体选择性金催化下合成α-氟代砜和β-氟代砜基砜

  摘要：

  我们开发了一种广泛应用的，高效的金催化合成α-氟砜和β-氟乙烯砜的方法。从炔基砜1开始，[Au] / HF / N-氧化物系统通过卡宾金中间体生成α-氟砜3，如果不使用N-氧化物，则将HF直接加成1即可通过苯乙炔生成乙烯基砜4。乙烯基氟金中间体。两种方法均具有良好的官能团耐受性，并且反应可在环境气氛中进行。

  DOI：

  10.1002/chem.201703179

文献信息

• Titanocene(II)-Promoted, One-Pot, Three-Component Coupling of Thioacetals, Alkynyl Sulfones, and Carbonyl Compounds:  Highly Stereoselective Formation of <i>tert</i>-Homopropargyl Alcohols
  作者：Takeshi Takeda、Maiko Ando、Takenori Sugita、Akira Tsubouchi

  DOI：10.1021/ol071077w

  日期：2007.7.1

  Titanocene alkylidene complexes, generated by desulfurizative titanation of thioacetals with Cp2Ti[P(OEt)3]2, reacted with alkynyl methyl sulfones to produce organotitanium species, which gave tert-homopropargyl alcohols with high diastereoselectivity on treatment with aromatic and alpha,beta-unsaturated ketones.

  通过用Cp2Ti [P（OEt）3] 2硫代乙缩醛的脱硫钛化反应生成的二茂钛亚烷基配合物，与炔基甲基砜反应生成有机钛物种，经芳族和α，β-不饱和芳烃处理后，得到对映体选择性高的对叔炔丙醇。酮。
• Regioselectivity in the reaction of tantalum-unsymmetrical acetylene complexes with carbonyl compounds. Stereoselective preparation of 1-alkenyl sulfides, .alpha.,.beta.-unsaturated esters, and amides
  作者：Yasutaka Kataoka、Jiro Miyai、Makoto Tezuka、Kazuhiko Takai、Kiitiro Utimoto

  DOI：10.1021/jo00051a023

  日期：1992.12

  Tantalum-alkyne complexes, derived by treatment of alkynes with low-valent tantalum (TaCl5 and zinc), react in situ with carbonyl compounds to give (E)-allylic alcohols stereoselectively. When unsymmetrical acetylenes are employed in the reaction, two regioisomeric allylic alcohols are produced. The regioselectivity of the reaction depends on the steric and electronic effects of the substituents on the acetylenes. For example, treatment of tantalum-alkyne complexes derived from methyl alkynyl sulfides with carbonyl compounds yields (E)-3-hydroxy-1-propenyl methyl sulfides in a regioselective manner. Tantalum-alkyne complexes derived from acetylenic esters react with carbonyl compounds regioselectively at the alpha-position of the esters to give Z-isomers of trisubstituted alpha,beta-unsaturated esters. In contrast, tantalum-alkyne complexes derived from acetylenic amides react with carbonyl compounds predominantly at the beta-position of the amides. The regioselectivity of the reaction between acetylenic amides and aldehydes, however, cannot be explained solely in terms of the steric and electronic effects of the substituents. Strong coordination of the amide group to the tantalum center could also be responsible for the observed selectivity, which is opposite to that observed with tantalum-acetylenic ester complexes.
• Divergent Regio‐ and Stereoselective Gold‐catalyzed Synthesis of α‐Fluorosulfones and β‐Fluorovinylsulfones from Alkynylsulfones
  作者：Xiaojun Zeng、Shiwen Liu、Gerald B. Hammond、Bo Xu

  DOI：10.1002/chem.201703179

  日期：2017.9.4

  We developed a widely applicable, highly efficient synthesis of α‐fluorosulfone and β‐fluorovinylsulfone catalyzed by gold. Starting with alkynyl sulfone 1, an [Au]/HF/N‐oxide system gives α‐fluorosulfone 3 via a gold carbene intermediate, and, if no N‐oxide is used, direct addition of HF to 1 gives vinyl sulfone 4 via a vinylfluoro gold intermediate. Both methods have good functional group tolerance

  我们开发了一种广泛应用的，高效的金催化合成α-氟砜和β-氟乙烯砜的方法。从炔基砜1开始，[Au] / HF / N-氧化物系统通过卡宾金中间体生成α-氟砜3，如果不使用N-氧化物，则将HF直接加成1即可通过苯乙炔生成乙烯基砜4。乙烯基氟金中间体。两种方法均具有良好的官能团耐受性，并且反应可在环境气氛中进行。