N-3-methyl-2-butenyl-N-(N'-Fmoc)-prolyl tryptophan methyl ester | 274677-63-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-3-methyl-2-butenyl-N-(N'-Fmoc)-prolyl tryptophan methyl ester
• 英文别名: 9H-fluoren-9-ylmethyl (2S)-2-[[(2S)-3-(1H-indol-3-yl)-1-methoxy-1-oxopropan-2-yl]-(3-methylbut-2-enyl)carbamoyl]pyrrolidine-1-carboxylate
• CAS: 274677-63-3
• 化学式: C₃₇H₃₉N₃O₅
• 分子量: 605.734
• InChiKey: DJYOAFQUYWTCRN-HEVIKAOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  91.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-3-methyl-2-butenyl-N-(N'-Fmoc)-prolyl tryptophan methyl ester 在 palladium diacetate 、 二甲基硫 、 氧气 、 溶剂黄146 、 甲基磺酰氯 、 三乙胺 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 苯 为溶剂， 20.0~65.0 ℃ 、101.33 kPa 条件下， 反应 4.17h， 生成 (+)-deoxyisoaustamide
  参考文献：
  名称：

  A Short Synthetic Route to (+)-Austamide, (+)-Deoxyisoaustamide, and (+)-Hydratoaustamide from a Common Precursor by a Novel Palladium-Mediated Indole → Dihydroindoloazocine Cyclization

  摘要：

  The first synthesis of (+)-austamide (1), (+)-deoxyisoaustamide (2), and (+)-hydratoaustamide (10) by a very direct route is described (Scheme 1). Starting from tryptophan methyl ester (3) intermediate 5 is generated in two steps in >98% overall yield. The key step in the synthesis is a novel cyclization of 5 involving organopalladium intermediates which gives the dihydroazocine 6. From this key intermediate the target structures are accessible in just a few steps as shown in Scheme 1. The remarkable conversion of 5 --> 6 can be rationalized by the mechanistic pathway shown in Scheme 2 that involves a multistep sequence which includes palladation, cyclization, and rearrangement.

  DOI：

  10.1021/ja026663t
• 作为产物：
  描述：

  3-甲基-2-丁烯醛 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 N-3-methyl-2-butenyl-N-(N'-Fmoc)-prolyl tryptophan methyl ester
  参考文献：
  名称：

  A Short Synthetic Route to (+)-Austamide, (+)-Deoxyisoaustamide, and (+)-Hydratoaustamide from a Common Precursor by a Novel Palladium-Mediated Indole → Dihydroindoloazocine Cyclization

  摘要：

  The first synthesis of (+)-austamide (1), (+)-deoxyisoaustamide (2), and (+)-hydratoaustamide (10) by a very direct route is described (Scheme 1). Starting from tryptophan methyl ester (3) intermediate 5 is generated in two steps in >98% overall yield. The key step in the synthesis is a novel cyclization of 5 involving organopalladium intermediates which gives the dihydroazocine 6. From this key intermediate the target structures are accessible in just a few steps as shown in Scheme 1. The remarkable conversion of 5 --> 6 can be rationalized by the mechanistic pathway shown in Scheme 2 that involves a multistep sequence which includes palladation, cyclization, and rearrangement.

  DOI：

  10.1021/ja026663t

文献信息

• Synthesis and Evaluation of Tryprostatin B and Demethoxyfumitremorgin C Analogues
  作者：Haishan Wang、Takeo Usui、Hiroyuki Osada、A. Ganesan

  DOI：10.1021/jm9905662

  日期：2000.4.1

  Tryprostatin B and demethoxyfumitremorgin C are fungal inhibitors of mammalian cell cycle progression at the G(2)/M transition. N-Alkyl derivatives of the L-TrP-L-Pro diketopiperazine were prepared as analogues of tryprostatin B, and two of these were more active than the natural product. A second series of cis- and trans-tetrahydro-beta-carbolines annulated to a diketopiperazine were prepared as analogues of demethoxyfumitremorgin C. The nature of the alkyl substituent, as well as its cis or trans relationship in the tetrahydro-beta-carboline ring, was found to have a significant effect on cytotoxic activity. Small cis-alkyl substituents fall into the demethoxyfumitremorgin C family, whereas bulky benzyl trans compounds appear to act via a different mechanism of action.
• A Short Synthetic Route to (+)-Austamide, (+)-Deoxyisoaustamide, and (+)-Hydratoaustamide from a Common Precursor by a Novel Palladium-Mediated Indole → Dihydroindoloazocine Cyclization
  作者：Phil S. Baran、E. J. Corey

  DOI：10.1021/ja026663t

  日期：2002.7.1

  The first synthesis of (+)-austamide (1), (+)-deoxyisoaustamide (2), and (+)-hydratoaustamide (10) by a very direct route is described (Scheme 1). Starting from tryptophan methyl ester (3) intermediate 5 is generated in two steps in >98% overall yield. The key step in the synthesis is a novel cyclization of 5 involving organopalladium intermediates which gives the dihydroazocine 6. From this key intermediate the target structures are accessible in just a few steps as shown in Scheme 1. The remarkable conversion of 5 --> 6 can be rationalized by the mechanistic pathway shown in Scheme 2 that involves a multistep sequence which includes palladation, cyclization, and rearrangement.