(+)-2-((1S,4R,5S,6S)-4,5,6-trihydroxycyclohex-2-en-1-yl)-1H-isoindole-1,3(2H)-dione | 913071-22-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (+)-2-((1S,4R,5S,6S)-4,5,6-trihydroxycyclohex-2-en-1-yl)-1H-isoindole-1,3(2H)-dione
• 英文别名: 2-[(1S,4R,5S,6S)-4,5,6-trihydroxycyclohex-2-en-1-yl]isoindole-1,3-dione
• CAS: 913071-22-4
• 化学式: C₁₄H₁₃NO₅
• 分子量: 275.261
• InChiKey: HXZGJONYTZSPRW-USZNOCQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  98.07
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (+)-2-((1S,4R,5S,6S)-4,5,6-trihydroxycyclohex-2-en-1-yl)-1H-isoindole-1,3(2H)-dione 在 咪唑 、 三乙酰氧基硼氢化钠 、 甲胺 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 (1S,4R,5S,6S)-N-({5-[2-chloro-5-(trifluoromethyl)phenyl]-2-furyl}methyl)-4,5,6-tris[(triethylsilyl)oxy]cyclohex-2-ene-1-amine
  参考文献：
  名称：

  Search for α-glucosidase inhibitors: New N-substituted valienamine and conduramine F-1 derivatives

  摘要：

  A solid-phase synthesis of new N-substituted valienamines has been developed and new synthesis of (+/-)-conduramine F-1, (-)-conduramine F-1, and (+)-ent-conduramine F-1 is presented, together with the preparation of N-benzylated conduramines F-1. N-Benzylation of both valienamine and (+)-ent-conduramine F-1 improves their inhibitory activity toward alpha-glucosidases significantly. The additional hydroxymethyl group makes valienamine derivatives more active than their (+)-ent-conduramine F-1 analogues. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.080
• 作为产物：
  描述：

  (-)-1L-2,3,4-tris-O-<(tert-butyl)dimethylsilyl>cyclohex-2-ene-1,3/2,4-tetrol 在 对甲苯磺酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 6.75h， 生成 (+)-2-((1S,4R,5S,6S)-4,5,6-trihydroxycyclohex-2-en-1-yl)-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Search for α-glucosidase inhibitors: New N-substituted valienamine and conduramine F-1 derivatives

  摘要：

  A solid-phase synthesis of new N-substituted valienamines has been developed and new synthesis of (+/-)-conduramine F-1, (-)-conduramine F-1, and (+)-ent-conduramine F-1 is presented, together with the preparation of N-benzylated conduramines F-1. N-Benzylation of both valienamine and (+)-ent-conduramine F-1 improves their inhibitory activity toward alpha-glucosidases significantly. The additional hydroxymethyl group makes valienamine derivatives more active than their (+)-ent-conduramine F-1 analogues. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.080