tert-butyl (5R,8S)-3-(4-methoxyphenyl)-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7-N-Boc-8-carboxylate | 453524-68-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (5R,8S)-3-(4-methoxyphenyl)-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7-N-Boc-8-carboxylate
• 英文别名: ditert-butyl (5R,8S)-3-(4-methoxyphenyl)-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7,8-dicarboxylate
• CAS: 453524-68-0
• 化学式: C₂₃H₃₂N₂O₆
• 分子量: 432.517
• InChiKey: DCVTZKUOBUYTQS-MBSDFSHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (5R,8S)-3-(4-methoxyphenyl)-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7-N-Boc-8-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 以91%的产率得到(5R,8S)-3-(4-methoxyphenyl)-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7-N-Boc-8-carboxylic acid
  参考文献：
  名称：

  Stereoselective Synthesis of Unnatural Spiroisoxazolinoproline-Based Amino Acids and Derivatives

  摘要：

  A route to spiroisoxazolinoproline-based amino acid derivatives is reported in which exo-methyleneprolinate 4 (tert-butyl ester) reacts as a dipolarophile with nitrile oxides to generate spiroisoxazolinoprolinates 7/10/11 in good yields (70-75%) and with ca. 1:4 cis:trans diastereo-selectivity. tert-Butyl spiroisoxazolinoprolinates were separable by column chromatography and amenable to scale-up leading to single diastereoisomers of N-Boc and N-Fmoc protected spiroisox-azolinoproline amino acids.

  DOI：

  10.1021/jo025611j
• 作为产物：
  描述：

  N-Boc-4-亚甲基-L-脯氨酸 在 4-二甲氨基吡啶 、 sodium hypochlorite 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 tert-butyl (5R,8S)-3-(4-methoxyphenyl)-1-oxa-2,7-diazaspiro[4.4]non-2-ene-7-N-Boc-8-carboxylate
  参考文献：
  名称：

  Stereoselective Synthesis of Unnatural Spiroisoxazolinoproline-Based Amino Acids and Derivatives

  摘要：

  A route to spiroisoxazolinoproline-based amino acid derivatives is reported in which exo-methyleneprolinate 4 (tert-butyl ester) reacts as a dipolarophile with nitrile oxides to generate spiroisoxazolinoprolinates 7/10/11 in good yields (70-75%) and with ca. 1:4 cis:trans diastereo-selectivity. tert-Butyl spiroisoxazolinoprolinates were separable by column chromatography and amenable to scale-up leading to single diastereoisomers of N-Boc and N-Fmoc protected spiroisox-azolinoproline amino acids.

  DOI：

  10.1021/jo025611j

文献信息

• Stereoselective Synthesis of Unnatural Spiroisoxazolinoproline-Based Amino Acids and Derivatives
  作者：Wei-Chieh Cheng、Yannan Liu、Melissa Wong、Marilyn M. Olmstead、Kit S. Lam、Mark J. Kurth

  DOI：10.1021/jo025611j

  日期：2002.8.1

  A route to spiroisoxazolinoproline-based amino acid derivatives is reported in which exo-methyleneprolinate 4 (tert-butyl ester) reacts as a dipolarophile with nitrile oxides to generate spiroisoxazolinoprolinates 7/10/11 in good yields (70-75%) and with ca. 1:4 cis:trans diastereo-selectivity. tert-Butyl spiroisoxazolinoprolinates were separable by column chromatography and amenable to scale-up leading to single diastereoisomers of N-Boc and N-Fmoc protected spiroisox-azolinoproline amino acids.