cis-4-isopropyl-2-methyl-butyrolactone | 89065-56-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: cis-4-isopropyl-2-methyl-butyrolactone
• 英文别名: 3-methyl-5-isopropylbutyrolactone；(3S,5S)-3-methyl-5-propan-2-yloxolan-2-one
• CAS: 89065-56-5；89065-57-6
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: RWYBSWPDYUWBIS-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-4-isopropyl-2-methyl-butyrolactone 在 rhodium on alumina lithium aluminium tetrahydride 、 氢气 作用下， 生成 (2S,4S)-2,5-Dimethyl-hexane-1,4-diol
  参考文献：
  名称：

  Remote asymmetric induction. A stereoselective approach to acyclic diols via cyclic hydroboration

  摘要：

  DOI：

  10.1021/ja00544a049
• 作为产物：
  描述：

  2-甲基-5-己烯-3-醇 在 吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 三乙胺 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 cis-4-isopropyl-2-methyl-butyrolactone
  参考文献：
  名称：

  Synthesis of .gamma.- and .delta.-lactones by free-radical annelation of Se-phenyl selenocarbonates

  摘要：

  A general method for the synthesis of gamma- and delta-lactones through the intramolecular addition of alkoxycarbonyl radicals, formed by reaction of Se-phenylselenocarbonates with n-Bu3SnH, onto carbon-carbon multiple bonds is described. This free-radical cyclization is characterized by high regioselectivity favoring exo addition and by a high ratio of cyclization to reduction. Monocyclic, fused bicyclic, and spirocyclic lactones are formed in good to excellent yield. Use of allyltri-n-butyltin as a chain-transfer agent in the place of n-Bu3SnH affords the corresponding 3-butenyl lactones.

  DOI：

  10.1021/jo00043a030

文献信息

• Synthesis of .gamma.- and .delta.-lactones by free-radical annelation of Se-phenyl selenocarbonates
  作者：Mario D. Bachi、Eric Bosch

  DOI：10.1021/jo00043a030

  日期：1992.8

  A general method for the synthesis of gamma- and delta-lactones through the intramolecular addition of alkoxycarbonyl radicals, formed by reaction of Se-phenylselenocarbonates with n-Bu3SnH, onto carbon-carbon multiple bonds is described. This free-radical cyclization is characterized by high regioselectivity favoring exo addition and by a high ratio of cyclization to reduction. Monocyclic, fused bicyclic, and spirocyclic lactones are formed in good to excellent yield. Use of allyltri-n-butyltin as a chain-transfer agent in the place of n-Bu3SnH affords the corresponding 3-butenyl lactones.
• Remote asymmetric induction. A stereoselective approach to acyclic diols via cyclic hydroboration
  作者：W. Clark Still、Kevin P. Darst

  DOI：10.1021/ja00544a049

  日期：1980.11