N-((14S)-14-hydroxy-14-allyl)acetyloyl-(2R)-bornane-10,2-sultam | 246167-29-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-((14S)-14-hydroxy-14-allyl)acetyloyl-(2R)-bornane-10,2-sultam
• 英文别名: (2S)-1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-2-hydroxypent-4-en-1-one；(2S)-1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-2-hydroxypent-4-en-1-one
• CAS: 246167-29-3
• 化学式: C₁₅H₂₃NO₄S
• 分子量: 313.418
• InChiKey: MTTQIJFQJCZXFI-NWJSVONSSA-N

物化性质

• 沸点：
  453.3±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-((14S)-14-hydroxy-14-allyl)acetyloyl-(2R)-bornane-10,2-sultam 在 silver(I) nitrite 、 phosphate buffer 、 碘 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 27.0h， 生成 (3S,5S)-(+)-3-hydroxy-5-hydroxymethyl-tetrahydrofuran-2-one
  参考文献：
  名称：

  Diastereoselective allylation of N-glyoxyloyl-(2R)-bornane-10,2-sultam and (1R)-8-phenylmenthyl glyoxylate: synthesis of (2S,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide

  摘要：

  The diastereoselective addition of allylsilanes and allylstannanes to N-glyoxyloyl-(2R)-bornane-10,2-sultam 1 and (1R)-8-phenylmenthyl glyoxylate 7 in the presence of Lewis acids has been studied. We obtained diastereoselectivities up to 84% and 94% for the allylation of 2 and 7, respectively. The application of the allylation products of 1 or 2 in the synthesis of 4-butanolides, for example (2S,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide 13 is presented. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.10.025
• 作为产物：
  描述：

  氯丙烯镁 、 (2R)-N-glyoxylbornane-10,2-sultam 在 titanium(IV) isopropylate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (2'R)-N-(2'-hydroxypent-4'-enoyl)-(2R)-10,2-sultam 、 N-((14S)-14-hydroxy-14-allyl)acetyloyl-(2R)-bornane-10,2-sultam
  参考文献：
  名称：

  Raszplewicz; Sikorska; Kiegiel, Polish Journal of Chemistry, 2002, vol. 76, # 11, p. 1595 - 1600

  摘要：

  DOI：

文献信息

• Diastereoselective Addition of Allyltrimethylsilane to<i>N</i>-Glyoxyloyl-(<i>2R</i>)-bornane-10,2-sultam. A new synthesis of (<i>S</i>)-1,2-Pentanediol
  作者：Katarzyna Kiegiel、Piotr Prokopowicz、Janusz Jurczak

  DOI：10.1080/00397919908085920

  日期：1999.11

  Addition of allyltrimethylsilane (3) to N-glyoxyloyl-(2R)-bornane-10,2-sultam (4) in the presence of Lewis acid afforded, in high diastereoselectivity, adduct (2'S)-6 which, after recrystallization, was hydrogenated to give optically pure (S)-1,2-pentanediol (1).
• Diastereoselective allylation of N-glyoxyloyl-(2R)-bornane-10,2-sultam and (1R)-8-phenylmenthyl glyoxylate: synthesis of (2S,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide
  作者：Katarzyna Kiegiel、Tomasz Bałakier、Piotr Kwiatkowski、Janusz Jurczak

  DOI：10.1016/j.tetasy.2004.10.025

  日期：2004.12

  The diastereoselective addition of allylsilanes and allylstannanes to N-glyoxyloyl-(2R)-bornane-10,2-sultam 1 and (1R)-8-phenylmenthyl glyoxylate 7 in the presence of Lewis acids has been studied. We obtained diastereoselectivities up to 84% and 94% for the allylation of 2 and 7, respectively. The application of the allylation products of 1 or 2 in the synthesis of 4-butanolides, for example (2S,4S)-2-hydroxy-4-hydroxymethyl-4-butanolide 13 is presented. (C) 2004 Elsevier Ltd. All rights reserved.
• Raszplewicz; Sikorska; Kiegiel, Polish Journal of Chemistry, 2002, vol. 76, # 11, p. 1595 - 1600
  作者：Raszplewicz、Sikorska、Kiegiel、Jurczak

  DOI：——

  日期：——