(3S,5R)-3-Bromo-3,5-dimethyl-dihydro-furan-2-one | 41788-52-7

• 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: (3S,5R)-3-Bromo-3,5-dimethyl-dihydro-furan-2-one
• 英文别名: cis-3-Bromodihydro-3,5-dimethylfuran-2(3H)-one；(3S,5R)-3-bromo-3,5-dimethyloxolan-2-one
• CAS: 41788-52-7
• 化学式: C₆H₉BrO₂
• 分子量: 193.04
• InChiKey: UIGUFPIRJDSCNF-XINAWCOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (3S,5R)-3-Bromo-3,5-dimethyl-dihydro-furan-2-one 在 三乙基硼 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 (3S,5R)-3,5-dimethyl-γ-butyrolactone 、 trans-2,4-dimethyl-γ-butyrolactone
  参考文献：
  名称：

  Versatile, high 2,4-syn dialkyl diastereoselection in the radical debromination of α-bromo-α-methyl-δ-valerolactones with tri-n-butyltin hydride and a catalytic amount of triethylborane

  摘要：

  An interesting 2,4-syn dialkyl diastereoselection has been observed in the radical debromination of alpha -bromo-alpha -methyl-delta -valerolactones. The reaction of 4-alkyl-2-bromo-3-hydroxy-2-methyl-5-pentanolides with Bu3SnH and a catalytic amount of Et3B gave, essentially, a single diastereomer with a 2,4-syn dialkyl relationship, independent of the orientation of the hydroxy Et substituent at C-3. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01507-6

文献信息

• Versatile, high 2,4-syn dialkyl diastereoselection in the radical debromination of α-bromo-α-methyl-δ-valerolactones with tri-n-butyltin hydride and a catalytic amount of triethylborane
  作者：Syun-ichi Kiyooka、Yong-Nan Li、Kazi A Shahid、Momotoshi Okazaki、Yoshihiro Shuto

  DOI：10.1016/s0040-4039(01)01507-6

  日期：2001.10

  An interesting 2,4-syn dialkyl diastereoselection has been observed in the radical debromination of alpha -bromo-alpha -methyl-delta -valerolactones. The reaction of 4-alkyl-2-bromo-3-hydroxy-2-methyl-5-pentanolides with Bu3SnH and a catalytic amount of Et3B gave, essentially, a single diastereomer with a 2,4-syn dialkyl relationship, independent of the orientation of the hydroxy Et substituent at C-3. (C) 2001 Elsevier Science Ltd. All rights reserved.