S-(tert-butyl) (4E,6E)-3-oxodeca-4,6-dienethioate | 140837-80-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: S-(tert-butyl) (4E,6E)-3-oxodeca-4,6-dienethioate
• 英文别名: t-butyl (4E,6E)-3-oxo-4,6-decadienthioate；S-tert-butyl (4E,6E)-3-oxodeca-4,6-dienethioate
• CAS: 140837-80-5
• 化学式: C₁₄H₂₂O₂S
• 分子量: 254.393
• InChiKey: BYIIKLXSCJCJDZ-XBLVEGMJSA-N

物化性质

• 沸点：
  352.8±25.0 °C(Predicted)
• 密度：
  0.997±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  、 S-(tert-butyl) (4E,6E)-3-oxodeca-4,6-dienethioate 在 silver trifluoroacetate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以143 mg的产率得到
  参考文献：
  名称：

  Total Synthesis and Biological Evaluation of the Tetramic Acid Based Natural Product Harzianic Acid and Its Stereoisomers

  摘要：

  The bioactive natural product harzianic acid was prepared for the first time in just six steps (longest linear sequence) with an overall yield of 22%. The identification of conditions to telescope amide bond formation and a Lacey-Dieckmann reaction into one pot proved important. The three stereoisomers of harzianic acid were also prepared, providing material for comparison of their biological activity. While all of the isomers promoted root growth, improved antifungal activity was unexpectedly associated with isomers in the enantiomeric series opposite that of harzianic acid.

  DOI：

  10.1021/ol503717r
• 作为产物：
  描述：

  S-tert-butyl 4-bromo-3-oxo-butanethioate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 S-(tert-butyl) (4E,6E)-3-oxodeca-4,6-dienethioate
  参考文献：
  名称：

  4-二乙基膦酰基-3-氧代丁硫醇叔丁基酯的制备及其在（E）-4-烯基-3-氧代酯和大环内酯类化合物的合成中的用途

  摘要：

  报道了4-二乙基膦酰基-3-氧代丁硫醇叔丁基酯的制备（1）和与醛和酮的Wadsworth-Emmons反应。在铜-（I）-三氟乙酸铜的存在下，通过酯交换反应将这些反应的一些产物转化为不饱和的3-氧代大环内酯或3-氧代环氧乙烷。

  DOI：

  10.1016/s0040-4039(00)95725-3

文献信息

• Further reactions of t-butyl 3-oxobutanthioate and t-butyl 4-diethyl-phosphono-3-oxobutanthioate : Carbonyl coupling reactions, amination, use in the preparation of 3-acyltetramic acids and application to the total synthesis of fuligorubin A.
  作者：Steven V. Ley、Stephen C. Smith、Peter R. Woodward

  DOI：10.1016/s0040-4020(01)88210-7

  日期：1992.1

  for the preparation of homologated derivatives suitable for amination in the presence of silver (I) trifluoroacetate to afford the corresponding β-ketoamides is discussed. In particular Wadsworth-Emmons coupling reactions of (2) with various carbonyl compounds gave good yields of E-substituted products. Many of the β-ketoamides were shown to be suitable precursors for 3-acyltetramic acids using a Dieckmann

  3-氧代丁氧硫醇叔丁酯（1）和4-二乙基氧代-3-氧杂丁硫醇叔丁酯（2）的制备适合于在三氟乙酸银（I）存在下进行胺化的同系化衍生物，得到相应的β讨论了β-酮酰胺。特别地，（2）与各种羰基化合物的Wadsworth-Emmons偶联反应给出了良好的E-取代产物收率。使用Dieckmann环化反应，以四正丁基氟化铵为环化碱，发现许多β-酮酰胺是3-酰基四酸的合适前体。这些新的反应应用于多烯3-酰基四酸富叶红素A的全合成。
• LEY S. V.; WOODWARD P. R., TETRAHEDRON LETT., 28,(1987) N 3, 345-346
  作者：LEY S. V.、 WOODWARD P. R.

  DOI：——

  日期：——
• Total Synthesis and Biological Evaluation of the Tetramic Acid Based Natural Product Harzianic Acid and Its Stereoisomers
  作者：Alan R. Healy、Francesco Vinale、Matteo Lorito、Nicholas J. Westwood

  DOI：10.1021/ol503717r

  日期：2015.2.6

  The bioactive natural product harzianic acid was prepared for the first time in just six steps (longest linear sequence) with an overall yield of 22%. The identification of conditions to telescope amide bond formation and a Lacey-Dieckmann reaction into one pot proved important. The three stereoisomers of harzianic acid were also prepared, providing material for comparison of their biological activity. While all of the isomers promoted root growth, improved antifungal activity was unexpectedly associated with isomers in the enantiomeric series opposite that of harzianic acid.
• Preparation of t-butyl 4-diethylphosphono-3-oxobutanethioate and use in the synthesis of (E)-4-alkenyl-3-oxoesters and macrolides
  作者：Steven V. Ley、Peter R. Woodward

  DOI：10.1016/s0040-4039(00)95725-3

  日期：1987.1

  The preparation of t-butyl 4-diethylphosphono-3-oxobutanethioate (1) and Wadsworth- Emmons reaction with aldehydes and ketones is reported. Some of the products of these reactions were converted to unsaturated 3-oxomacrolides or 3-oxodiolides by transesterification in the presence of copper-(I)-trifluoroacetate.

  报道了4-二乙基膦酰基-3-氧代丁硫醇叔丁基酯的制备（1）和与醛和酮的Wadsworth-Emmons反应。在铜-（I）-三氟乙酸铜的存在下，通过酯交换反应将这些反应的一些产物转化为不饱和的3-氧代大环内酯或3-氧代环氧乙烷。