S-ethyl (S)-3-hydroxyheptanethioate | 1039034-39-3

• 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-ethyl (S)-3-hydroxyheptanethioate
• 英文别名: S-ethyl (3S)-3-hydroxyheptanethioate
• CAS: 1039034-39-3
• 化学式: C₉H₁₈O₂S
• 分子量: 190.307
• InChiKey: UDGAZCXOKIJFBE-QMMMGPOBSA-N

物化性质

• 沸点：
  279.3±23.0 °C(predicted)
• 密度：
  1.022±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-ethyl (S)-3-hydroxyheptanethioate 、 叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以89%的产率得到S-ethyl (S)-3-(tert-butyldimethylsiloxy)heptanethioate
  参考文献：
  名称：

  Asymmetric Total Synthesis of Botcinins C, D, and F

  摘要：

  Stereoselective total synthesis of botcinins C, D, and F is effectively carried out through asymmetric aldol reactions, 6-endo ring closure, and Sml(12)-mediated 3,4-trans or -cis stereoselective intramolecular Reformatsky reaction. Rapid esterification of the main skeleton of botcinins with the chiral side chain using MNBA and DMAP produced botcinin D, an antifungal chemical against a pathogen of rice blast disease.

  DOI：

  10.1021/ol801066y
• 作为产物：
  描述：

  正戊醛 、 1-ethylthio-1-(trimethylsiloxy)ethene 在 tin(II) trifluoromethanesulfonate 、 (R)-1-methyl-2-(1-naphthylaminomethyl)pyrrolidine 作用下， 以 丙腈 为溶剂， 反应 4.0h， 以82%的产率得到S-ethyl (S)-3-hydroxyheptanethioate
  参考文献：
  名称：

  Asymmetric Total Synthesis of Botcinins C, D, and F

  摘要：

  Stereoselective total synthesis of botcinins C, D, and F is effectively carried out through asymmetric aldol reactions, 6-endo ring closure, and Sml(12)-mediated 3,4-trans or -cis stereoselective intramolecular Reformatsky reaction. Rapid esterification of the main skeleton of botcinins with the chiral side chain using MNBA and DMAP produced botcinin D, an antifungal chemical against a pathogen of rice blast disease.

  DOI：

  10.1021/ol801066y

文献信息

• Stereoselective Total Synthesis of the Proposed Structure of 2-Epibotcinolide
  作者：Isamu Shiina、Yu-ji Takasuna、Ryo-suke Suzuki、Hiromi Oshiumi、Yuri Komiyama、Seiichi Hitomi、Hiroki Fukui

  DOI：10.1021/ol062058+

  日期：2006.11.9

  [Structure: see text] The total synthesis of pseudo 2-epibotcinolide (1b) through several featured synthetic approaches has been attained. First, the chiral linear precursors of the nine-membered ring compound is stereoselectively constructed by the asymmetric aldol reaction for producing beta-hydroxy ester units. Second, the key cyclization reaction to form the nine-membered lactone moiety is efficiently

  [结构：见正文]通过几种有特色的合成方法，已完成了拟合成的2-表鬼臼乙内酰胺（1b）的合成。首先，通过不对称醛醇缩合反应立体选择性地构建九元环化合物的手性线性前体，以产生β-羟基酯单元。其次，通过2-甲基-6-硝基苯甲酸酐（MNBA）与碱性促进剂促进的极其简便而强大的混合酸酐方法，可以有效地完成形成九元内酯部分的关键环化反应。
• Asymmetric Total Synthesis of Botcinins C, D, and F
  作者：Hiroki Fukui、Isamu Shiina

  DOI：10.1021/ol801066y

  日期：2008.7.17

  Stereoselective total synthesis of botcinins C, D, and F is effectively carried out through asymmetric aldol reactions, 6-endo ring closure, and Sml(12)-mediated 3,4-trans or -cis stereoselective intramolecular Reformatsky reaction. Rapid esterification of the main skeleton of botcinins with the chiral side chain using MNBA and DMAP produced botcinin D, an antifungal chemical against a pathogen of rice blast disease.