macrocarpamine | 66408-46-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - Pleiocarpaman生物碱
• 英文名称: macrocarpamine
• 英文别名: methyl (8R,13E,14S,16S,17S,18S)-17-[(E)-2-[(1S,12S,13R,18R)-3,20-dimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.02,10.04,9.013,18]icosa-2(10),4,6,8,16-pentaen-17-yl]ethenyl]-13-ethylidene-1,11-diazapentacyclo[12.3.1.02,7.08,17.011,16]octadeca-2,4,6-triene-18-carboxylate
• CAS: 66408-46-6
• 化学式: C₄₁H₄₆N₄O₃
• 分子量: 642.841
• InChiKey: NOKYQXVIWFQLED-HXCLOJFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  48
• 可旋转键数：
  4
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  50.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  macrocarpamine 280.0~290.0 ℃ 、13.33 Pa 条件下， 生成 anhydromacrosalhine-methine
  参考文献：
  名称：

  大果豆，双歧双倍生物碱，美国阿尔斯通尼亚大叶沃尔（Wall。alstonia macrophylla WALL）。167.自然的Mittelungüber组织† ‡

  摘要：

  Macrocarpamine，一种来自Alstonia macrophylla WALL的新的双吲哚生物碱。

  DOI：

  10.1002/hlca.19780610130
• 作为产物：
  描述：

  alstophyllane 在 盐酸 、 sodium periodate 、 水 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 吡啶 、 水 为溶剂， 反应 15.0h， 生成 macrocarpamine
  参考文献：
  名称：

  Enantiospecific Total Synthesis of (−)-Anhydromacrosalhine-methine and Partial Synthesis of the Antiamoebic Bisindole Alkaloid (−)-Macrocarpamine¹

  摘要：

  An enantiospecific total synthesis of (-)-anhydromacrosalhine-methine (7a) was completed from D-(+)-tryptophan via the asymmetric Pictet-Spengler reaction. In addition, a partial synthesis of (-)-anhydromacrosalhine-methine (7a) was carried out from the natural product (+)-ajmaline (10). The coupling reaction of plant-derived (+)-pleiocarpamine (8) with synthetic diene 7a provided the antiamoebic bisindole alkaloid (-)-macrocarpamine (1) in 75% yield. This sequence serves as the first example of the action of a nucleophile at [at C(2)] on a protonated form [C(3)] of pleiocarpamine 8 in the Alstonia series to provide a bisindole alkaloid.

  DOI：

  10.1021/jo971570t

文献信息

• Partial synthesis of the antiamoebic bisindole alkaloid (−)-macrocarpamine
  作者：Tong Gan、James M. Cook

  DOI：10.1016/0040-4039(96)01010-6

  日期：1996.7

  The partial synthesis of the antiamoebic bisindole alkaloid (−)-macrocarpamine 1 has been completed by coupling (−)-anhydromacrosalhine-methine 2 with plant-derived (+)-pleiocarpamine 3 in anhydrous 0.2 N HCl in THF in 75% yield.

  通过在无水0.2 N HCl的THF中将（-）-脱水大麦草碱-次甲基2与植物衍生的（+）-多果糖胺3偶联，已经完成了抗厌氧双吲哚生物碱（-）-大果酚胺1的部分合成，产率为75％。
• Enantiospecific Total Synthesis of (−)-Anhydromacrosalhine-methine and Partial Synthesis of the Antiamoebic Bisindole Alkaloid (−)-Macrocarpamine¹
  作者：Tong Gan、James M. Cook

  DOI：10.1021/jo971570t

  日期：1998.3.1

  An enantiospecific total synthesis of (-)-anhydromacrosalhine-methine (7a) was completed from D-(+)-tryptophan via the asymmetric Pictet-Spengler reaction. In addition, a partial synthesis of (-)-anhydromacrosalhine-methine (7a) was carried out from the natural product (+)-ajmaline (10). The coupling reaction of plant-derived (+)-pleiocarpamine (8) with synthetic diene 7a provided the antiamoebic bisindole alkaloid (-)-macrocarpamine (1) in 75% yield. This sequence serves as the first example of the action of a nucleophile at [at C(2)] on a protonated form [C(3)] of pleiocarpamine 8 in the Alstonia series to provide a bisindole alkaloid.
• Macrocarpamin, ein neues Bisindolalkaloid aus<i>Alstonia macrophylla</i>W<scp>ALL</scp>. 167. Mittelung über organische Naturstoffe
  作者：Friedrich Mayerl、Manfred Hesse

  DOI：10.1002/hlca.19780610130

  日期：1978.1.25

  Macrocarpamine, a new bisindole alkaloid from Alstonia macrophylla WALL.

  Macrocarpamine，一种来自Alstonia macrophylla WALL的新的双吲哚生物碱。