2-(1,1-dimethylallyl) gramine | 22102-56-3

• 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: 2-(1,1-dimethylallyl) gramine
• 英文别名: 3-(3-Dimethylamino-methyl-indolyl-(2))-3-methyl-buten-(1)；N,N-dimethyl-1-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methanamine
• CAS: 22102-56-3
• 化学式: C₁₆H₂₂N₂
• 分子量: 242.364
• InChiKey: IZFFPZDNTSCJAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(1,1-dimethylallyl) gramine 在 盐酸 、 lithium hydroxide 、 三丁基膦 、 3 A molecular sieve 、 camphor-10-sulfonic acid 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 80.0h， 生成 [1-13C]-2-(1,1-dimethyl-2-propenyl)-L-tryptophan methyl ester
  参考文献：
  名称：

  Studies on the biosynthesis of paraherquamide. Construction of the amino acid framework

  摘要：

  It has been previously established in this laboratory that the beta -methyl-beta -hydroxyproline moiety of the potent anthelmintic agent paraherquamide A, is biosynthetically derived from L-isoleucine. The downstream events from L-Ile to paraherquamide A have now been investigated. The synthesis of [1-(13)C]-labeled L-beta -methylproline is described by means of a Hoffman-Loeffler-Freytag reaction sequence from [1-(13)C]-L-Ile. This amino acid is shown to be a direct biosynthetic precursor to paraherquamide A by feeding and incorporation experiments in growing cultures of Penicillum fellutanum. Three tryptophan-containing dipeptides of L-beta -methylproline have been constructed: [(13)C(2)]-2-(l,1-dimethyl-2-propenyl)-L-tryptophanyl-3(S)-methyl-L-proline [(13)C(2)]-3(S)-methyl-L-prolyl-2-(l,1-dimethyl-2-propenyl)-L-tryptophan and [(13)C(2)]-cyclo-2-(l,1-dimethyl-2-propenyl)-L-tryptophan-3(S)-methyl-L-proline. [alpha-(15)N, 1-(13)C]-2-(1,1-Dimethyl-2-propenyl)-L-tryptophan was also prepared but none of these substances were found to serve as biosynthetic precursors to paraherquamide A. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00449-5
• 作为产物：
  描述：

  2-(2-methylbut-3-en-2-yl)-1H-indole 生成 2-(1,1-dimethylallyl) gramine
  参考文献：
  名称：

  RUSSELL R. A., AUSTRAL. J. CHEM. , 1975, 28, NO 11, 2535-2538

  摘要：

  DOI：

文献信息

• Total Synthesis of VM55599. Utilization of an Intramolecular Diels−Alder Cycloaddition of Potential Biogenetic Relevance
  作者：Emily M. Stocking、Juan F. Sanz-Cervera、Robert M. Williams

  DOI：10.1021/ja993791h

  日期：2000.3.1

  The total synthesis of VM55599, a natural metabolite of Penicillium sp. IMI332995, has been achieved via an intramolecular Diels−Alder cycloaddition of a reverse isoprene moiety across an azadiene system. The diastereoselectivity of the intramolecular Diels−Alder cycloaddition has biogenetic implications and is discussed in the context of the biogenetic relationship of VM55599 to the paraherquamides

  VM55599 的全合成，一种青霉属的天然代谢物。IMI332995 是通过反向异戊二烯部分跨氮杂二烯系统的分子内 Diels-Alder 环加成实现的。分子内 Diels-Alder 环加成的非对映选择性具有生物遗传学意义，并在 VM55599 与 paraherquamides 的生物遗传关系的背景下进行了讨论。
• Studies on indolic mould metabolites. Total synthesis of l-prolyl-2-methyltryptophan anhydride and deoxybrevianamide e
  作者：R. Ritchie、J.E. Saxton

  DOI：10.1016/0040-4020(81)85025-9

  日期：1981.1

  Syntheses of l - prolyl - 2 - methyl - l - tryptophan anhydride, l -prolyl - 2 - methyl - d - tryptophan anhydride, deoxybrevianamide E, and l - prolyl - 2 - (1,1 - dimethylallyl) - d- tryptophan anhydride are described. A route for the conversion of deoxybrevianamide E into brevianamide E has also been examined.

  1-prolyl-2-甲基-1-色氨酸酐，1-prolyl-2-甲基-d-色氨酸酐，脱氧布雷维酰胺E和1-prolyl-2-（1,1-二甲基烯丙基）-d-色氨酸酐的合成被描述。还研究了将脱氧布雷维酰胺E转化为布雷维酰胺E的途径。
• <i>des</i>-Formylflustrabromine (dFBr): A Structure–Activity Study on Its Ability To Potentiate the Action of Acetylcholine at α4β2 Nicotinic Acetylcholine Receptors
  作者：Małgorzata Dukat、Atul Jain、Nadezhda German、Rossana Ferrara-Pontoriero、Yanzhou Huang、Yilong Ma、Marvin K. Schulte、Richard A. Glennon

  DOI：10.1021/acschemneuro.8b00156

  日期：2018.12.19

  modulator (PAM) at α4β2 nicotinic acetylcholine receptors (nAChRs). We previously deconstructed this agent to determine which of its structural features contribute to its actions and have identified an agent that might serve as the basis for a " working pharmacophore". Here, we elaborate the dFBr (1; EC50 = 0.2 μM) structure to identify how various structural modifications impact its actions. Electrophysiological

  天然吲哚生物碱去甲酰基氟乙溴（dFBr; 1）是最早被证明对α4β2烟碱乙酰胆碱受体（nAChRs）具有选择性正变构调节剂（PAM）的药物之一。我们以前对这种药物进行了解构，以确定其结构特征中的哪些有助于其作用，并确定了可能用作“有效药效基团”基础的药物。在这里，我们详细阐述了dFBr（1; EC50 = 0.2μM）结构，以确定各种结构修饰如何影响其作用。非洲爪蟾卵母细胞的电生理研究确定了几种具有dFBr样效力的化合物，一种化合物是5溴类似物1（即5-溴dFBr； 25； EC50 = 0.4μM），其功效是1的5倍以上。在α4β2nAChRs处的PAM。
• Studies on the syntheses of heterocyclic compounds. Part 876. The chiral total synthesis of brevianamide E and deoxybrevianamide E
  作者：Tetsuji Kametani、Naoaki Kanaya、Masataka Ihara

  DOI：10.1039/p19810000959

  日期：——

  The chiral total synthesis of brevianamide E (1) and deoxybrevianamide E (2) starting from L-proline is described. Condensation of 2-(1,1-dimethylallyl)-3-dimethylaminomethylindole (3) and (–)-methyl 1,4-dioxoperhydropyrrolo[1,2-a]pyrazine-3-carboxylate (7) derived from L-proline followed by demethoxycarbonylation gave (–)-deoxybrevianamide E (2) and its epimer (10). Photo-oxygenations of (2) and (10)

  描述了从L-脯氨酸开始的手性总的brevianamide E（1）和deoxybrevianamide E（2）的合成。衍生自L-脯氨酸的2-（1,1-二甲基烯丙基）-3-二甲基氨基甲基吲哚（3）和（–）-甲基1,4-二氧杂氢吡咯并[1,2 - a ]吡嗪-3-羧酸酯（7）的缩合反应通过脱甲氧基羰基化得到（-）-脱氧短戊酰胺E（2）及其差向异构体（10）。（2）和（10）的光氧合形成了（–）-brevianamide E（14）及其三个立体异构体（15），（16）和（17）。通过该合成将布雷维酰胺E（14）的绝对立体化学确定为4a S，5a R，10a S，11a S。
• Study on the biosynthesis of the notoamides: pinacol-type rearrangement of the isoprenyl unit in deoxybrevianamide E and 6-hydroxydeoxybrevianamide E
  作者：Hikaru Kato、Yuichi Nakamura、Jennifer M. Finefield、Hideharu Umaoka、Takashi Nakahara、Robert M. Williams、Sachiko Tsukamoto

  DOI：10.1016/j.tetlet.2011.10.065

  日期：2011.12

  reverse-prenylated indole alkaloids, deoxybrevianamide E and 6-hydroxydeoxybrevianamide E, are proposed as biosynthetic precursors for advanced metabolites isolated from the marine-derived Aspergillus sp. In order to uncover the role of the alkaloids in the biosynthetic pathway, the feeding experiments of the [13C]2–[15N]-labeled deoxybrevianamide E and 6-hydroxydeoxybrevianamide E were performed to afford the

  两种反向异戊二烯化吲哚生物碱 deoxybrevianamide E 和 6-hydroxydeoxybrevianamide E 被提议作为从海洋来源的曲霉属中分离的高级代谢物的生物合成前体。为了揭示生物碱在生物合成途径中的作用，进行了 [ 13 C] 2 – [ 15 N] 标记的脱氧短酰胺 E 和 6-羟基脱氧短酰胺 E的饲养实验，以提供通过氧化产生的代谢物和异戊二烯基单元的连续频哪醇型重排。