methyl 3-hydroxy-2-methyl-3-phenylhex-5-enedithioate | 1454846-20-8

• 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: methyl 3-hydroxy-2-methyl-3-phenylhex-5-enedithioate
• CAS: 1454846-20-8
• 化学式: C₁₄H₁₈OS₂
• 分子量: 266.428
• InChiKey: WTYIMJYBZRXMRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  77.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-hydroxy-2-methyl-3-phenylhex-5-enedithioate 在 yttrium(III) trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 48.0h， 以50%的产率得到1-苯基-2-丁烯-1-酮
  参考文献：
  名称：

  Y(OTf)3 catalyzed substitution dependent oxidative C(sp3)–C(sp3) cleavage and regioselective dehydration of β-allyl-β-hydroxydithioesters: alternate route to α,β-unsaturated ketones and functionalized dienes

  摘要：

  beta-Allyl-beta-hydroxydithioesters have been generated by the regioselective Grignard addition to the beta-oxodithioesters. They have been successfully employed in selective C(sp(3))-C(sp(3)) bond cleavage to construct alpha,beta-unsaturated ketone residues by the treatment of an emerging catalyst yttrium(III)triflate for the first time. On the other hand, hetaryl substituted beta-allyl-beta-hydroxydithioesters led to the useful diene precursors through selective dehydration under the similar conditions. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.092
• 作为产物：
  描述：

  methyl 2-methyl-3-oxo-3-phenylpropane(dithioate) 、 烯丙基溴化镁 以 四氢呋喃 为溶剂， 反应 5.0h， 以55%的产率得到methyl 3-hydroxy-2-methyl-3-phenylhex-5-enedithioate
  参考文献：
  名称：

  Y(OTf)3 catalyzed substitution dependent oxidative C(sp3)–C(sp3) cleavage and regioselective dehydration of β-allyl-β-hydroxydithioesters: alternate route to α,β-unsaturated ketones and functionalized dienes

  摘要：

  beta-Allyl-beta-hydroxydithioesters have been generated by the regioselective Grignard addition to the beta-oxodithioesters. They have been successfully employed in selective C(sp(3))-C(sp(3)) bond cleavage to construct alpha,beta-unsaturated ketone residues by the treatment of an emerging catalyst yttrium(III)triflate for the first time. On the other hand, hetaryl substituted beta-allyl-beta-hydroxydithioesters led to the useful diene precursors through selective dehydration under the similar conditions. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.092