allyl 2-isopropylbenzene sulfide | 73059-75-3

• 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: allyl 2-isopropylbenzene sulfide
• 英文别名: Allyl-2-isopropylphenyl-sulfid；(2-Isopropylphenyl)allyl sulfide；1-propan-2-yl-2-prop-2-enylsulfanylbenzene
• CAS: 73059-75-3
• 化学式: C₁₂H₁₆S
• 分子量: 192.325
• InChiKey: UBUPZPUJUCZPKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-异丙基苯硫酚 、 3-溴丙烯 在 正丁基锂 作用下， 以 乙醚 、 六甲基磷酰三胺 为溶剂， 反应 0.5h， 以57%的产率得到allyl 2-isopropylbenzene sulfide
  参考文献：
  名称：

  Asymmetric Copper-Catalyzed [2,3]-Sigmatropic Rearrangements of Alkyl- and Aryl-Substituted Allyl Sulfides

  摘要：

  The asymmetric copper-catalyzed generation and subsequent [2,3]-sigmatropic rearrangement of sulfur ylides is strongly dependent on the structure of the starting allyl sulfide. A series of alkyl and aryl substituted allyl sulfides (2a-i) were reacted with ethyl diazoacetate in the presence of copper triflate (CuOTf) and a C-2-symmetric bis-oxazoline ligand (5a-c). The degree of asymmetric induction ranged from 2.8% for allyl methyl sulfide (2a) to 60% for (1S,2S,5R)-(+)-allyl menthyl sulfide (2d). The enantioselectivity of the reactions was also dependent on the electronic nature of the sulfide; allyl phenyl sulfide (2e) gave a 14% ee, whereas allyl p-methoxyphenyl sulfide (2i) produced only an 8% ee. The stereochemistry of 2d and (1R,2S,5R)-(+)-allyl menthyl sulfide (7) was assigned on the basis of NMR spectroscopic experiments.

  DOI：

  10.1021/jo991842n

文献信息

• Rotational isomerism in N-(N-heteroaryl)arenesulphenamides
  作者：Robert S. Atkinson、Brian D. Judkins、Bhalchandra Patwardhan

  DOI：10.1039/p29790001490

  日期：——

  N-(1,2-Dihydro-2-oxoquinolin-1-yl)-N-(1-methylallyl)-4-chlorobenzenesulphenamide (5) has previously been isolated in two stereoisomeric forms. From examination of a number of analogues of (5), it is concluded that the phenomenon which allows isolation of these stereoisomers is restricted rotation around the N–N bond.

  N-（1,2-二氢-2-氧喹啉-1-基）-N-（1-甲基烯丙基）-4-氯苯磺酰胺（5）先前已分离为两种立体异构形式。通过对（5）的许多类似物的研究，可以得出结论，允许分离这些立体异构体的现象是限制了N–N键周围的旋转。
• Asymmetric Copper-Catalyzed [2,3]-Sigmatropic Rearrangements of Alkyl- and Aryl-Substituted Allyl Sulfides
  作者：Douglas W. McMillen、Norbert Varga、Beth Ann Reed、Claudia King

  DOI：10.1021/jo991842n

  日期：2000.4.1

  The asymmetric copper-catalyzed generation and subsequent [2,3]-sigmatropic rearrangement of sulfur ylides is strongly dependent on the structure of the starting allyl sulfide. A series of alkyl and aryl substituted allyl sulfides (2a-i) were reacted with ethyl diazoacetate in the presence of copper triflate (CuOTf) and a C-2-symmetric bis-oxazoline ligand (5a-c). The degree of asymmetric induction ranged from 2.8% for allyl methyl sulfide (2a) to 60% for (1S,2S,5R)-(+)-allyl menthyl sulfide (2d). The enantioselectivity of the reactions was also dependent on the electronic nature of the sulfide; allyl phenyl sulfide (2e) gave a 14% ee, whereas allyl p-methoxyphenyl sulfide (2i) produced only an 8% ee. The stereochemistry of 2d and (1R,2S,5R)-(+)-allyl menthyl sulfide (7) was assigned on the basis of NMR spectroscopic experiments.