N-[3(R)-methylpentanoyl]-(1S,2R)-bornane-2,10-sultam | 104651-15-2

• 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-[3(R)-methylpentanoyl]-(1S,2R)-bornane-2,10-sultam
• 英文别名: (3R)-1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-3-methylpentan-1-one；(3R)-1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-3-methylpentan-1-one
• CAS: 104651-15-2
• 化学式: C₁₆H₂₇NO₃S
• 分子量: 313.461
• InChiKey: RTIADOJSMVPATK-BRXULGCHSA-N

物化性质

• 沸点：
  418.7±28.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[3(R)-methylpentanoyl]-(1S,2R)-bornane-2,10-sultam 在 lithium hydroxide 作用下， 以73%的产率得到(R)-3-甲基戊酸
  参考文献：
  名称：

  Practical Synthesis of (+)-Alloisoleucine

  摘要：

  Subsequent treatment of N-crotoyl-(1S,2R)-bornane-10,2-sultam with EtMgCl, recrystallization of the product and saponification, afforded R-(-)-3-methylpenthanoic acid which was used for acylation of (1R,2S)-bomane-10,2-sultam. The product was converted into N-[(2S,3R)-2-amino-3 -methylpentanoyl]-(1R,2S)-bornane-10,2-sultam by hydroxyamination with 1-chloro-1-nitrosocyclohexane, followed by reduction of the hydroxylamine grouping. Saponification of the sultam imide provided (+)-alloisoleucine.

  DOI：

  10.1080/00397910008087404
• 作为产物：
  描述：

  (2R)-bornane-10,2-sultam 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 乙醇 为溶剂， 生成 N-[3(R)-methylpentanoyl]-(1S,2R)-bornane-2,10-sultam
  参考文献：
  名称：

  Efficient asymmetric hydrogenations of camphor-soltam-imide-conjugated alkenes.

  摘要：

  DOI：

  10.1016/s0040-4039(00)83972-6

文献信息

• Asymmetric induction at C(β) and C(α) of N-enoyl sultams by 1,4-hydride addition/enolate trapping
  作者：Wolfgang Oppolzer、Giovanni Poli

  DOI：10.1016/s0040-4039(00)85046-7

  日期：1986.1

  Conjugate addition of L-Selectride to α, β-enoyl sultams and followed by electrophilic trapping of the resulting enolates gave in one operation saturated imides with high β- and/or α- stereodifferentiation.

  共轭加成三仲丁基硼氢化锂的α，β烯酰基磺内酰胺和接着将得到的烯醇化物的电俘获在具有高β-和/或α-stereodifferentiation一个操作饱和酰亚胺得到。
• OPPOLZER, W.;MILLS, R. J.;REGLIER, M., TETRAHEDRON LETT., 1986, 27, N 2, 183-186
  作者：OPPOLZER, W.、MILLS, R. J.、REGLIER, M.

  DOI：——

  日期：——
• OPPOLZER W.; POLI G., TETRAHEDRON LETT., 27,(1986) N 39, 4717-4720
  作者：OPPOLZER W.、 POLI G.

  DOI：——

  日期：——
• Efficient asymmetric hydrogenations of camphor-soltam-imide-conjugated alkenes.
  作者：Wolfgang Oppolzer、Robert J. Mills、Marius Reglier

  DOI：10.1016/s0040-4039(00)83972-6

  日期：1986.1
• Practical Synthesis of (+)-Alloisoleucine
  作者：Czeslaw Belzecki、Jerzy Trojnar、Marek Chmielewski

  DOI：10.1080/00397910008087404

  日期：2000.1

  Subsequent treatment of N-crotoyl-(1S,2R)-bornane-10,2-sultam with EtMgCl, recrystallization of the product and saponification, afforded R-(-)-3-methylpenthanoic acid which was used for acylation of (1R,2S)-bomane-10,2-sultam. The product was converted into N-[(2S,3R)-2-amino-3 -methylpentanoyl]-(1R,2S)-bornane-10,2-sultam by hydroxyamination with 1-chloro-1-nitrosocyclohexane, followed by reduction of the hydroxylamine grouping. Saponification of the sultam imide provided (+)-alloisoleucine.