(E,2R)-1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-2-hydroxyoct-4-en-1-one | 192766-71-5

• 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: (E,2R)-1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-2-hydroxyoct-4-en-1-one
• 英文别名: (E,2R)-1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-2-hydroxyoct-4-en-1-one
• CAS: 192766-71-5
• 化学式: C₁₈H₂₉NO₄S
• 分子量: 355.499
• InChiKey: FIQKMEKXKGZBDN-OAIWFRFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (E,2R)-1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-2-hydroxyoct-4-en-1-one 在 platinum(IV) oxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 生成 (R)-(+)-1,2-辛二醇
  参考文献：
  名称：

  The asymmetric ene reaction of N-glyoxyloyl-(2R)-bornane-10,2-sultam with 1-pentene and 1-hexene

  摘要：

  The asymmetric ene reaction of N-glyoxyloyl-(2R)-bornane-10,2-sultarn 2 and its hemiacetal 3 with I-pentene 4 and I-hexene 5 in the presence of Lewis acids is reported. All the ene reactions studied led to diastereoisomeric mixtures of olefins 6 and 7 or 8 and 9, with predominance of products of the (S) absolute configuration on the newly formed stereogenic center. The absolute configuration (via X-ray analysis of 6 and chemical correlation) and the extent of asymmetric induction were established. Stereochemical models are proposed. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00130-4
• 作为产物：
  描述：

  1-己烯 、 (S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-hydroxy-2-methoxy-ethanone 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 80.0h， 生成 (E,2R)-1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-2-hydroxyoct-4-en-1-one 、 (E)-(S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-hydroxy-oct-4-en-1-one
  参考文献：
  名称：

  The asymmetric ene reaction of N-glyoxyloyl-(2R)-bornane-10,2-sultam with 1-pentene and 1-hexene

  摘要：

  The asymmetric ene reaction of N-glyoxyloyl-(2R)-bornane-10,2-sultarn 2 and its hemiacetal 3 with I-pentene 4 and I-hexene 5 in the presence of Lewis acids is reported. All the ene reactions studied led to diastereoisomeric mixtures of olefins 6 and 7 or 8 and 9, with predominance of products of the (S) absolute configuration on the newly formed stereogenic center. The absolute configuration (via X-ray analysis of 6 and chemical correlation) and the extent of asymmetric induction were established. Stereochemical models are proposed. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00130-4

文献信息

• The asymmetric ene reaction of N-glyoxyloyl-(2R)-bornane-10,2-sultam with 1-pentene and 1-hexene
  作者：Artur Jeżewski、Katarzyna Chajewska、Zbigniew Wielogórski、Janusz Jurczak

  DOI：10.1016/s0957-4166(97)00130-4

  日期：1997.6

  The asymmetric ene reaction of N-glyoxyloyl-(2R)-bornane-10,2-sultarn 2 and its hemiacetal 3 with I-pentene 4 and I-hexene 5 in the presence of Lewis acids is reported. All the ene reactions studied led to diastereoisomeric mixtures of olefins 6 and 7 or 8 and 9, with predominance of products of the (S) absolute configuration on the newly formed stereogenic center. The absolute configuration (via X-ray analysis of 6 and chemical correlation) and the extent of asymmetric induction were established. Stereochemical models are proposed. (C) 1997 Elsevier Science Ltd.