(E)-(S)-4-Benzyloxycarbonylamino-4-cyclohexyl-2-methyl-but-2-enoic acid ethyl ester | 143914-85-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-(S)-4-Benzyloxycarbonylamino-4-cyclohexyl-2-methyl-but-2-enoic acid ethyl ester
• 英文别名: ethyl (E,4S)-4-cyclohexyl-2-methyl-4-(phenylmethoxycarbonylamino)but-2-enoate
• CAS: 143914-85-6
• 化学式: C₂₁H₂₉NO₄
• 分子量: 359.466
• InChiKey: GXCQLRVPZHGAGR-JRJUITNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  (E)-(S)-4-Benzyloxycarbonylamino-4-cyclohexyl-2-methyl-but-2-enoic acid ethyl ester 在 碘 、 silver trifluoromethanesulfonate 、 碳酸氢钠 作用下， 以 四氯化碳 为溶剂， 反应 0.75h， 生成 (S)-2-((4S,5R)-4-Cyclohexyl-2-oxo-oxazolidin-5-yl)-2-iodo-propionic acid ethyl ester 、 (R)-2-((4S,5R)-4-Cyclohexyl-2-oxo-oxazolidin-5-yl)-2-iodo-propionic acid ethyl ester
  参考文献：
  名称：

  Stereoselective silver triflate-mediated iodocyclization of carbamates

  摘要：

  Iodocyclization of carbamates involving electron-deficient olefins, (i.e. alpha,beta-unsaturated esters) is greatly facilitated by the use of silver(I) triflate and proceeds with excellent trans ring stereoselectivity. During this process, the resultant iodides can undergo epimerization, the rate of which is solvent-dependent.

  DOI：

  10.1016/s0040-4039(00)74232-8
• 作为产物：
  描述：

  Cbz-环己基-L-甘氨酸 在 lithium aluminium tetrahydride 、 三氧化硫吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 (E)-(S)-4-Benzyloxycarbonylamino-4-cyclohexyl-2-methyl-but-2-enoic acid ethyl ester
  参考文献：
  名称：

  Stereoselective silver triflate-mediated iodocyclization of carbamates

  摘要：

  Iodocyclization of carbamates involving electron-deficient olefins, (i.e. alpha,beta-unsaturated esters) is greatly facilitated by the use of silver(I) triflate and proceeds with excellent trans ring stereoselectivity. During this process, the resultant iodides can undergo epimerization, the rate of which is solvent-dependent.

  DOI：

  10.1016/s0040-4039(00)74232-8

文献信息

• Stereoselective silver triflate-mediated iodocyclization of carbamates
  作者：Y Guindon、A Slassi、É Ghiro、G Bantle、G Jung

  DOI：10.1016/s0040-4039(00)74232-8

  日期：1992.7

  Iodocyclization of carbamates involving electron-deficient olefins, (i.e. alpha,beta-unsaturated esters) is greatly facilitated by the use of silver(I) triflate and proceeds with excellent trans ring stereoselectivity. During this process, the resultant iodides can undergo epimerization, the rate of which is solvent-dependent.