2-methyl-2-(3-(2-methyl-prop-1-ene))-1,3-dithiane | 65447-88-3

• 分子结构分类: 有机化合物 - 有机硫化合物
• 英文名称: 2-methyl-2-(3-(2-methyl-prop-1-ene))-1,3-dithiane
• 英文别名: 2-methyl-2-(2-methyl-allyl)-[1,3]dithiane；2-methyl-2-(2-methyl-2-propenyl)-1,3-dithiane；2-methyl-2-(2-methylprop-2-enyl)-1,3-dithiane
• CAS: 65447-88-3
• 化学式: C₉H₁₆S₂
• 分子量: 188.358
• InChiKey: XGQBFOCFUQOMQO-UHFFFAOYSA-N

物化性质

• 沸点：
  258.0±23.0 °C(Predicted)
• 密度：
  0.994±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-methyl-2-(3-(2-methyl-prop-1-ene))-1,3-dithiane 在 奎宁环 、 sodium periodate 、 osmium (III) chloride 、 potassium carbonate 、 sodium thiosulfate 、 potassium hexacyanoferrate(III) 作用下， 以 甲醇 、 水 为溶剂， 反应 20.0h， 生成 syn-2-methyl-2-(3-(2-methyl-propane-1,2-diol))-1,3-dithiane 1-oxide
  参考文献：
  名称：

  Highly chemoselective osmium-mediated dihydroxylation of 2-vinyl and 2-allyl-1,3-dithiane 1-oxides

  摘要：

  Chemoselective dihydroxylation of the double bonds of alkenyl-substituted 1,3-dithiane 1-oxide derivatives takes place without competing sulfur oxidation using osmium trichloride and potassium Ferricyanide. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00923-5
• 作为产物：
  描述：

  甲基碘化镁 、 2,2'-Methanediylbis(2-methyl-1,3-dithiane) 在 bis(triphenylphosphine)nickel(II) chloride 作用下， 以70%的产率得到2-methyl-2-(3-(2-methyl-prop-1-ene))-1,3-dithiane
  参考文献：
  名称：

  螯合辅助将 CS 债券转换为 CC 债券

  摘要：

  当底物包含两个以上可以与金属物种共生相互作用的近端杂原子时，这些碳-杂原子键之一可以被激活。该策略已应用于某些刚性双二硫缩醛的镍催化交叉偶联反应。杂原子取代基如羟基、甲氧基或氨基也有助于脂肪族二硫缩醛的链烯化；和高烯丙醇、醚和胺分别以相当好的收率获得。聚硫醚转化为环丙烷衍生物。

  DOI：

  10.1080/10426509708545523

文献信息

• Hoppmann,A. et al., Justus Liebigs Annalen der Chemie, 1977, p. 1547 - 1556
  作者：Hoppmann,A. et al.

  DOI：——

  日期：——
• Chelation Assistance in the Activation of Csp3-S Bonds in Nickel-Catalyzed Cross-Coupling Reactions
  作者：Ken-Tsung Wong、Tien-Min Yuan、Maw Cherng Wang、Hsiao-Hsian Tung、Tien-Yau Luh

  DOI：10.1021/ja00099a009

  日期：1994.10

  An unprecedented chelation approach to activate C(sp)3-S bonds in nickel-catalyzed cross-coupling reactions is described. Our theme was based on the formation of a chelation complex which results in the enhancement of the reactivity of aliphatic carbon-sulfur bonds. When two dithioacetal functionalities are located in close proximity, selective olefination of one of these two dithioacetal groups can thus be achieved conveniently. Depending on the relative positions of the newly formed double bond and the remaining dithioacetal group, tandem olefination occurs to give the corresponding 1,5-bis-silyl-substituted pentadienes. Various neighboring heteroatom substituents (OR, OH, NR(2) as well as SR groups) can facilitate the olefination of a dithioacetal group. Poly(thioether) linkage afforded the corresponding degradation products via a B-sulfur elimination process. 1,3-Dimercapto- and 1,3-dithiolatopropanes furnish the cyclopropane formation under nickel-catalyzed reaction conditions. The reaction of a dihydrothiopyran with MeMgI in the presence of the nickel catalyst proceeds via a sulfur-coordinated ir-allyl complex, which can further activate the CS bond to give vinylcyclopropane.
• CRISTAU H.-J.; VORS J.-P.; CHRISTOL H., TETRAHEDRON LETT., 1979, NO 26, 2377-2380
  作者：CRISTAU H.-J.、 VORS J.-P.、 CHRISTOL H.

  DOI：——

  日期：——