3-乙酰基四氢-4H-噻喃-4-酮 | 144535-06-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-乙酰基四氢-4H-噻喃-4-酮
• 中文别名: 4H-噻喃-4-酮,3-乙酰基四氢-(9CI)
• 英文名称: 3-acetyldihydro-2H-thiopyran-4(3H)-one
• 英文别名: 3-Acetylthian-4-one
• CAS: 144535-06-8
• 化学式: C₇H₁₀O₂S
• 分子量: 158.221
• InChiKey: CIWZKUDPJMGYSD-UHFFFAOYSA-N

物化性质

• 沸点：
  297.9±40.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1,3-bis(3,4-dimethoxyphenyl)prop-2-en-1-ol 、 3-乙酰基四氢-4H-噻喃-4-酮 在 (11bS)-4-羟基-2,6-二[2,4,6-三(异丙基)苯基]-二萘并[2,1-d:1',2'-f][1,3,2]二氧杂磷杂卓4-氧化物 、 盐酸羟胺 、 三乙胺 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 48.0h， 生成 (3aR,7aR)-3a-[(E,1S)-1,3-bis(3,4-dimethoxyphenyl)prop-2-enyl]-3-methyl-6,7-dihydro-4H-thiopyrano[3,4-d][1,2]oxazol-7a-ol
  参考文献：
  名称：

  An Organocatalytic Asymmetric Allylic Alkylation Allows Enantioselective Total Synthesis of Hydroxymetasequirin-A and Metasequirin-B Tetramethyl Ether Diacetates

  摘要：

  The first highly stereoselective organocatalytic intermolecular allylic alkylation of allylic alcohols with 1,3-dicarbonyls has been developed to allow the first enantioselective total synthesis of hydroxymetasequirin-A and metasequirin-B tetramethyl ether diacetates.

  DOI：

  10.1021/ol4037055
• 作为产物：
  描述：

  四氢噻喃-4-酮 、 乙酰氯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.67h， 以35%的产率得到3-乙酰基四氢-4H-噻喃-4-酮
  参考文献：
  名称：

  An Organocatalytic Asymmetric Allylic Alkylation Allows Enantioselective Total Synthesis of Hydroxymetasequirin-A and Metasequirin-B Tetramethyl Ether Diacetates

  摘要：

  The first highly stereoselective organocatalytic intermolecular allylic alkylation of allylic alcohols with 1,3-dicarbonyls has been developed to allow the first enantioselective total synthesis of hydroxymetasequirin-A and metasequirin-B tetramethyl ether diacetates.

  DOI：

  10.1021/ol4037055

文献信息

• A short synthesis of (−)-(4R,5S)-sitophilure using the regio- and stereoselective reduction of 3-acyltetrahydrothiopyran-4-ones with baker's yeast
  作者：Tamotsu Fujisawa、Bingidimi I. Mobele、Makoto Shimizu

  DOI：10.1016/s0040-4039(00)61147-4

  日期：1992.9

  Bakers' yeast reduction of 3-acyltetrahydrothiopyran-4-ones is regio- and enantioselective, yielding predominantly (3R,4S)-3-acyl-4- hydroxytetrahydrothiopyranes with high optical purity. This reduction method coupled with the Raney-nickel desulfurization provides a ready access to the rice and maize weevils aggregation pheromone, (−)-(4R,5S)-sitophilure, in high optical purity.

  贝克的3-酰基四氢噻喃-4-酮的酵母还原具有区域和对映选择性，主要产生具有高光学纯度的（3 R，4 S）-3-酰基-4-羟基四氢噻喃。这种还原方法与阮内镍脱硫技术相结合，可提供高光学纯度的水稻和玉米象鼻虫聚集信息素（-）-（4 R，5 S）-sitophilure。
• An Organocatalytic Asymmetric Allylic Alkylation Allows Enantioselective Total Synthesis of Hydroxymetasequirin-A and Metasequirin-B Tetramethyl Ether Diacetates
  作者：Pu-Sheng Wang、Xiao-Le Zhou、Liu-Zhu Gong

  DOI：10.1021/ol4037055

  日期：2014.2.7

  The first highly stereoselective organocatalytic intermolecular allylic alkylation of allylic alcohols with 1,3-dicarbonyls has been developed to allow the first enantioselective total synthesis of hydroxymetasequirin-A and metasequirin-B tetramethyl ether diacetates.