2,2,4-triphenyl-3,4-dihydro-2H-thiopyran

• 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: 2,2,4-triphenyl-3,4-dihydro-2H-thiopyran
• 英文别名: 2,2,4-Triphenyl-3,4-dihydrothiopyran
• 化学式: C₂₃H₂₀S
• 分子量: 328.478
• InChiKey: FSPMBRXXLHCWCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  1,1-二苯乙烯 、 (E)-2-(2-phenyl-ethenyl)-4,4-dimethyl-1,3-oxathiane 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以88%的产率得到2,2,4-triphenyl-3,4-dihydro-2H-thiopyran
  参考文献：
  名称：

  4,4-二甲基-2-苯乙烯-1,3-氧杂蒽与烯烃的新型串联[4 + +2]环加成消除反应

  摘要：

  一种新型串联[4 + 2] 1,3- oxathianes的环加成-消除反应1A，b通过促进烯烃四氯化钛，得到3,4-二氢-2- ħ -thiopyrans 3被开发。4,4-二甲基-2-苯乙烯基-1,3-氧杂蒽（1a）被用作高反应性硫肉桂醛的合成等同物。在1,3- oxathianes 4-位偕二甲基的取代基1是此环加成-消除反应的固有部分。

  DOI：

  10.1016/s0040-4039(99)02064-x

文献信息

• A novel tandem [4++2] cycloaddition–elimination reaction of 4,4-dimethyl-2-styryl-1,3-oxathianes with olefins
  作者：Kiyoharu Nishide、Shin-ichi Ohsugi、Manabu Node

  DOI：10.1016/s0040-4039(99)02064-x

  日期：2000.1

  A novel tandem [4++2] cycloaddition–elimination reaction of 1,3-oxathianes 1a,b with olefins promoted by titanium tetrachloride to give 3,4-dihydro-2H-thiopyrans 3 was developed. 4,4-Dimethyl-2-styryl-1,3-oxathiane (1a) was used as a synthetic equivalent of a highly reactive thiocinnamaldehyde. Geminal dimethyl substituents at the 4-position of 1,3-oxathianes 1 are an intrinsic part of this cycloaddition–elimination

  一种新型串联[4 + 2] 1,3- oxathianes的环加成-消除反应1A，b通过促进烯烃四氯化钛，得到3,4-二氢-2- ħ -thiopyrans 3被开发。4,4-二甲基-2-苯乙烯基-1,3-氧杂蒽（1a）被用作高反应性硫肉桂醛的合成等同物。在1,3- oxathianes 4-位偕二甲基的取代基1是此环加成-消除反应的固有部分。
• A novel tandem [4++2] cycloaddition–elimination reaction: 2-alkenyl-4,4-dimethyl-1,3-oxathianes as synthetic equivalents for α,β-unsaturated thioaldehydes
  作者：Shin-ichi Ohsugi、Kiyoharu Nishide、Manabu Node

  DOI：10.1016/s0040-4020(03)00179-0

  日期：2003.3

  The first tandem cationic [4(+)+2] polar cycloaddition-elimination reaction of 1-thia-1,3-butadienyl cations B with olefins to afford directly 3,4-dihydro-2H-thiopyrans D is described. The cations B were easily accessible by treatment of monothioacetals A, particularly the 2-alkenyl-4,4-dimethyl-1,3-oxathianes 1, with a hard Lewis acid. In this novel reaction, 2-alkenyl-4,4-dimethyl-1,3-oxathianes were utilized as synthetic equivalents for highly reactive alpha,beta-unsaturated thioaldehydes. The effect of geminal dimethyl substituents on the oxathianes 1 and the mechanistic aspect of the reaction are considered. The reaction's asymmetric version was also investigated using a chiral oxathiane 4 derived from (-)-(IR,2R,5R)-2-(I-mercapto-l-methylethyl)-5-methylcyclohexanol. Although the enantioselectivities were moderate, the whole process can be done under odorless conditions. (C) 2003 Elsevier Science Ltd. All rights reserved.