(5R)-3-ethyl-5-methyl-5-[2-(tert-butoxycarbonylamino)ethyl]furan-2(5H)-one | 825653-37-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (5R)-3-ethyl-5-methyl-5-[2-(tert-butoxycarbonylamino)ethyl]furan-2(5H)-one
• 英文别名: tert-butyl N-[2-[(2R)-4-ethyl-2-methyl-5-oxofuran-2-yl]ethyl]carbamate
• CAS: 825653-37-0
• 化学式: C₁₄H₂₃NO₄
• 分子量: 269.341
• InChiKey: OKGSAJXTJFGQTR-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5R)-3-ethyl-5-methyl-5-[2-(tert-butoxycarbonylamino)ethyl]furan-2(5H)-one 在 硅酸四乙酯 、 cesium fluoride 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (3S,3aR,6aR)-3-ethylhexahydro-6a-methyl-2H-furo[3,2-b]pyrrol-2-one
  参考文献：
  名称：

  Ammonia-Promoted Fragmentation of 2-Alkyl- and 2,4-Dialkyl-3-iodo-1- oxocyclohexan-2,4-carbolactones

  摘要：

  2-Alkyl- and 2,4-dialkyl-3-iodo-1-oxocyclohexan-2,4-carbolactones undergo ammonia-promoted fragmentation reactions to provide butenolides, gamma-butyrolactone, and/or, beta,gamma-epoxycyclohexanones. Product distribution is governed by the relative size of the substituents at C-2 and C-4 of the cyclohexanones. Butenolide amide, the major product from the fragmentation, is further converted into their respective piperidinone and pyrrolidine derivatives.

  DOI：

  10.1021/jo048408s
• 作为产物：
  描述：

  (2R,3R,4R)-2-ethyl-3-iodo-4-methyl-1-oxocyclohexane-2,4-carbolactone 在 吡啶 、 lead(IV) acetate 、 氨 、 四氯化锡 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (5R)-3-ethyl-5-methyl-5-[2-(tert-butoxycarbonylamino)ethyl]furan-2(5H)-one
  参考文献：
  名称：

  Ammonia-Promoted Fragmentation of 2-Alkyl- and 2,4-Dialkyl-3-iodo-1- oxocyclohexan-2,4-carbolactones

  摘要：

  2-Alkyl- and 2,4-dialkyl-3-iodo-1-oxocyclohexan-2,4-carbolactones undergo ammonia-promoted fragmentation reactions to provide butenolides, gamma-butyrolactone, and/or, beta,gamma-epoxycyclohexanones. Product distribution is governed by the relative size of the substituents at C-2 and C-4 of the cyclohexanones. Butenolide amide, the major product from the fragmentation, is further converted into their respective piperidinone and pyrrolidine derivatives.

  DOI：

  10.1021/jo048408s

文献信息

• Ammonia-Promoted Fragmentation of 2-Alkyl- and 2,4-Dialkyl-3-iodo-1- oxocyclohexan-2,4-carbolactones
  作者：Mingshi Dai、Xuqing Zhang、Seock-Kyu Khim、Arthur G. Schultz

  DOI：10.1021/jo048408s

  日期：2005.1.1

  2-Alkyl- and 2,4-dialkyl-3-iodo-1-oxocyclohexan-2,4-carbolactones undergo ammonia-promoted fragmentation reactions to provide butenolides, gamma-butyrolactone, and/or, beta,gamma-epoxycyclohexanones. Product distribution is governed by the relative size of the substituents at C-2 and C-4 of the cyclohexanones. Butenolide amide, the major product from the fragmentation, is further converted into their respective piperidinone and pyrrolidine derivatives.