reticulatate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: reticulatate
• 英文别名: Thorectandroic acid；2-pyrido[3,4-b]indol-2-ylbenzoic acid
• 化学式: C₁₈H₁₂N₂O₂
• 分子量: 288.305
• InChiKey: ZFQPREUMWUPFMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  海洋活性生物碱 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以54%的产率得到reticulatate
  参考文献：
  名称：

  Investigations on the Reactivity of Fascaplysin, Part II, General Stability Considerations and Products Formed with Nucleophiles

  摘要：

  Reversible deprotonation of fascaplysin (1) was achieved with non-nucleophilic bases (Scheme 1). Under basic aqueous conditions, opening of ring D of 1 occurred, yielding zwitter-ionic reticulatine 2a. whereas. in a methoxide-containing MeOH solution, an unexpected addition of three molecules of MeOH to the pyridinium ring produced an isomer mixture 3 of a trimethoxy-substituted compound (Scheme 2). Transformation of the keto group of 1 to the oxime JA took place in the presence of pyridine as base (Scheme 3). Grignard and alkyllithium reagents added as expected to the keto group of 1. providing tertiary alcohols 5 and 6 (Scheme 4).

  DOI：

  10.1002/1522-2675(20010418)84:4<867::aid-hlca867>3.0.co;2-a

文献信息

• Investigations on the Reactivity of Fascaplysin, Part II, General Stability Considerations and Products Formed with Nucleophiles
  作者：Heinz Fretz、Katharina Ucci-Stoll、Paul Hug、Joseph Schoepfer、Marc Lang

  DOI：10.1002/1522-2675(20010418)84:4<867::aid-hlca867>3.0.co;2-a

  日期：2001.4.18

  Reversible deprotonation of fascaplysin (1) was achieved with non-nucleophilic bases (Scheme 1). Under basic aqueous conditions, opening of ring D of 1 occurred, yielding zwitter-ionic reticulatine 2a. whereas. in a methoxide-containing MeOH solution, an unexpected addition of three molecules of MeOH to the pyridinium ring produced an isomer mixture 3 of a trimethoxy-substituted compound (Scheme 2). Transformation of the keto group of 1 to the oxime JA took place in the presence of pyridine as base (Scheme 3). Grignard and alkyllithium reagents added as expected to the keto group of 1. providing tertiary alcohols 5 and 6 (Scheme 4).