(R)-(-)-3-methylpentanoic acid chloride | 287734-99-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: (R)-(-)-3-methylpentanoic acid chloride
• 英文别名: 3-Methyl-pentanoyl chloride；(3R)-3-methylpentanoyl chloride
• CAS: 287734-99-0
• 化学式: C₆H₁₁ClO
• 分子量: 134.606
• InChiKey: OGMHLZVDKIJTMN-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-(-)-3-methylpentanoic acid chloride 在 NaH(TMS)2 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 N-[(2S,3R)-2-(N-hydroxyamino)-3-methylpentanoyl]-(1R,2S)-bornane-2,10-sultam
  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：

  (R)-3-甲基戊酸 在 氯化亚砜 作用下， 以83%的产率得到(R)-(-)-3-methylpentanoic acid chloride
  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

文献信息

• Copper‐Catalyzed Enantioselective Conjugate Addition of Dialkylzinc Reagents to α′‐Oxy Enones
  作者：Jesús M. García、Alberto González、Bharat G. Kardak、José M. Odriozola、Mikel Oiarbide、Jesús Razkin、Claudio Palomo

  DOI：10.1002/chem.200801343

  日期：2008.10.10
• 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.