(2R,3R,4R)-4-Hydroxy-3-iodo-2-(3-methoxy-benzyl)-pyrrolidine-1-carboxylic acid 2,2,2-trichloro-ethyl ester | 84110-08-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2R,3R,4R)-4-Hydroxy-3-iodo-2-(3-methoxy-benzyl)-pyrrolidine-1-carboxylic acid 2,2,2-trichloro-ethyl ester
• CAS: 84110-08-7
• 化学式: C₁₅H₁₇Cl₃INO₄
• 分子量: 508.568
• InChiKey: UXJZPTIHSUJWNH-JHJVBQTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  59.0
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R)-4-Hydroxy-3-iodo-2-(3-methoxy-benzyl)-pyrrolidine-1-carboxylic acid 2,2,2-trichloro-ethyl ester 在 氢氧化钾 、 sodium 2,2,2-trifluoroacetate 、 sodium carbonate 、 溶剂黄146 、 三氟乙酸 、 锌 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 18.5h， 生成 N-<(fluorenylmethoxy)carbonyl>-3β,4α-dihydroxy-2β-(m-methoxybenzyl)pyrrolidine
  参考文献：
  名称：

  Structure-activity relationships of synthetic antibiotic analogs of anisomycin

  摘要：

  A general synthetic sequence was used to synthesize a series of analogues of anisomycin, and the biological activities of the new synthetic analogues as antiprotozoals, antifungals, and antibacterials were evaluated. The synthetic antibiotics included 3 beta-acetoxy-4 alpha-hydroxy-2 beta-(p-methylbenzyl)pyrrolidine (1b), 3 beta-acetoxy-2 beta-benzyl-4 alpha-hydroxypyrrolidine (1c), 3 beta-acetoxy-4 alpha-hydroxy-2 beta-(m-methoxybenzyl)pyrrolidine (1d), 3 beta-acetoxy-4 alpha-hydroxy-2 beta-(o-methoxybenzyl)pyrrolidine (1e), 3 beta-acetoxy-4 alpha-hydroxy-2 beta-(alpha-methyl-p-methoxybenzyl)pyrrolidine (1f), and 3 beta-acetoxy-4 alpha-hydroxy-2 beta-(alpha-phenyl-p-methoxybenzyl)pyrrolidine (1g). The anisomycin analogues showed activity against protozoa and fungi, but this activity was restricted primarily to the p-methylbenzyl and benzyl analogues 1b and 1c. The activities dropped dramatically as the methoxy substituent was moved to the meta or ortho positions of the benzyl group (1d and 1e) or a methyl or phenyl group was attached at the alpha-benzyl carbon (1f and 1g).

  DOI：

  10.1021/jm00358a003
• 作为产物：
  描述：

  2-(m-methoxybenzyl)-3-pyrroline 在 sodium hydroxide 、 N-碘代丁二酰亚胺 、 高氯酸 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 2.0h， 生成 (2R,3R,4R)-4-Hydroxy-3-iodo-2-(3-methoxy-benzyl)-pyrrolidine-1-carboxylic acid 2,2,2-trichloro-ethyl ester
  参考文献：
  名称：

  Structure-activity relationships of synthetic antibiotic analogs of anisomycin

  摘要：

  A general synthetic sequence was used to synthesize a series of analogues of anisomycin, and the biological activities of the new synthetic analogues as antiprotozoals, antifungals, and antibacterials were evaluated. The synthetic antibiotics included 3 beta-acetoxy-4 alpha-hydroxy-2 beta-(p-methylbenzyl)pyrrolidine (1b), 3 beta-acetoxy-2 beta-benzyl-4 alpha-hydroxypyrrolidine (1c), 3 beta-acetoxy-4 alpha-hydroxy-2 beta-(m-methoxybenzyl)pyrrolidine (1d), 3 beta-acetoxy-4 alpha-hydroxy-2 beta-(o-methoxybenzyl)pyrrolidine (1e), 3 beta-acetoxy-4 alpha-hydroxy-2 beta-(alpha-methyl-p-methoxybenzyl)pyrrolidine (1f), and 3 beta-acetoxy-4 alpha-hydroxy-2 beta-(alpha-phenyl-p-methoxybenzyl)pyrrolidine (1g). The anisomycin analogues showed activity against protozoa and fungi, but this activity was restricted primarily to the p-methylbenzyl and benzyl analogues 1b and 1c. The activities dropped dramatically as the methoxy substituent was moved to the meta or ortho positions of the benzyl group (1d and 1e) or a methyl or phenyl group was attached at the alpha-benzyl carbon (1f and 1g).

  DOI：

  10.1021/jm00358a003