(1H-indol-3-yl)-(trimethylsiloxy)acetonitrile | 444108-97-8

• 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: (1H-indol-3-yl)-(trimethylsiloxy)acetonitrile
• 英文别名: 2-(1H-indole-3-yl)-2-(trimethylsiloxy)acetonitrile；2-(1H-indol-3-yl)-2-((trimethylsilyl)oxy)acetonitrile；2-(1H-indol-3-yl)-2-trimethylsilyloxyacetonitrile
• CAS: 444108-97-8
• 化学式: C₁₃H₁₆N₂OSi
• 分子量: 244.368
• InChiKey: LMTULMHNNLQNOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  48.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1H-indol-3-yl)-(trimethylsiloxy)acetonitrile 在 盐酸 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 反应 4.5h， 生成 (5Z)-2-(1H-indole-3-carbonyl)-5-[(6-methoxy-1H-indol-3-yl)methylidene]-1H-imidazol-4-one
  参考文献：
  名称：

  Synthesis of the marine alkaloids rhopaladins A, B, C and D

  摘要：

  The total synthesis of all four known rhopaladins, A-D, isolated from the Okinawan marine tunicate Rhopalaea sp., in two synthetic steps is described, involving an imidate based cyclization with tryptophan esters as the key step to afford the appropriately substituted imidazolinone unit. A short and efficient new synthesis of indol-3-yl-carbonyl nitriles from indol-3-yl-carboxaldehydes and trimethylsilyl cyanide, followed by oxidation with DDQ is also described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00171-0
• 作为产物：
  描述：

  3-吲哚甲醛 、 三甲基氰硅烷 以 乙腈 为溶剂， 反应 2.0h， 以67%的产率得到(1H-indol-3-yl)-(trimethylsiloxy)acetonitrile
  参考文献：
  名称：

  非手性海绵衍生和合成的溴吲哚作为针对 PANC-1 肿瘤细胞的选择性细胞毒素的潜力

  摘要：

  我们对具有体外实体瘤选择性的天然产物的分离和表征的追求是通过访问印度太平洋海绵提取物存储库来推动的。在该项目中，通过体外纸片扩散测定 (DDA) 和 IC 50测定，从美国 NCI 天然产物存储库获得的一种单链海绵的提取物显示，对人胰腺癌细胞系 (PANC- 1)相对于人淋巴细胞白血病细胞系(CCRF-CEM)。鉴定出两种溴化吲哚，即已知的 6-溴锥虫胺 ( 1 ) 和新衍生物 6-Br-8-酮-锥虫胺 A ( 2 )，2（天然产物的 IC 50为 1.5 μM，天然产物的 IC 50 为 4.1 μM）合成材料）被确定为提取物针对 PANC-1 肿瘤细胞系的细胞毒活性的原因。新的天然产品和十种其他类似物已准备好进行进一步的 SAR 测试。

  DOI：

  10.1016/j.tet.2017.11.029

文献信息

• Methyltriphenylphosphonium iodide catalyzes the addition of trimethylsilyl cyanide to aldehydes
  作者：Rubén Córdoba、Joaquı́n Plumet

  DOI：10.1016/s0040-4039(03)01391-1

  日期：2003.8

  Methyltriphenylphosphonium iodide catalyzes the formation of cyanohydrin trimethylsilyl ethers of aliphatic, aromatic and heterocyclic aldehydes.

  甲基三苯基碘化碘催化脂肪族，芳香族和杂环醛的氰醇三甲基甲硅烷基醚的形成。
• Hydroboration, Cyanosilylation, and Sequential Cyanosilylation and Hydroboration of Carbonyl Compounds in the Presence of a Ti^IV Amido Complex as an Efficient Catalyst
  作者：Adimulam Harinath、Jayeeta Bhattcharjee、Koteswar Rao Gorantla、Bhabani S. Mallik、Tarun K. Panda

  DOI：10.1002/ejoc.201800547

  日期：2018.6.29

  A titanium(IV) amido complex – [κ2‐(C5H4N)CH2NP(=Se)Ph2}Ti(NMe2)3] (1) – was synthesized and used as a catalyst for catalytic hydroboration, cyanosilylation, and sequential hydroboration/cyanosilylation of various aldehydes and ketones, with tolerance of a number of active functional groups, at ambient temperature. The mechanism was explored by kinetics study and theoretical calculations.

  的钛（IV）酰氨复杂- [κ 2 - （C 5 H ^ 4 N）CH 2 NP（= Se）的博士2 }的Ti（NME 2）3 ]（1） -的合成，并用作催化的催化剂在环境温度下，对各种醛和酮进行硼氢化，氰基硅烷化和顺序硼氢化/氰基硅烷化，并具有许多活性官能团的耐受性。通过动力学研究和理论计算探索了该机理。
• Alkali metal complexes as efficient catalysts for hydroboration and cyanosilylation of carbonyl compounds
  作者：Adimulam Harinath、Jayeeta Bhattacharjee、Hari Pada Nayek、Tarun K. Panda

  DOI：10.1039/c8dt02032a

  日期：——

  N-adamantyliminopyrolyl ligand 2-(AdNCH)–C4H3NH (L–H) and alkali metal hexamethyldisilazides [MN(SiMe3)2] (M = Li, Na and K) to afford the dimeric [2-(AdNCH)–C4H3NLi(THF)}2] (1), [2-(AdNCH)–C4H3N}Na(THF)1.5}2] (2) and polymeric [2-(AdNCH)–C4H3NK(THF)}n] (3) complexes at ambient temperature. A one-pot reaction between L–H, [KN(SiMe3)2] and alkaline earth metal diiodide (AeI2) in a 2 : 2 : 1 molar ratio, which

  我们在这里报告N-金刚烷基吡咯基配体2-（AdN CH）–C 4 H 3 NH（L–H）与碱金属六甲基二硅叠氮化物[MN（SiMe 3）2 ]（M = Li，Na和K）之间的反应二聚体[2-（AdN CH）–C 4 H 3 NLi（THF）} 2 ]（1），[2-（AdN CH）–C 4 H 3 N} Na（THF）1.5 } 2 ] （2）和聚合的[2-（AdN CH）–C 4 H 3 NK（THF）} n ]（3）在环境温度下的配合物。L–H，[KN（SiMe 3）2 ]与碱土金属二碘化物（AeI 2）之间以2：2：1的摩尔比进行一锅反应，导致形成杂配Ae金属络合物[κ]还报告了2- 2-（AdN CH）–C 4 H 3 N} 2 Ae（THF）2 ] [Ae = Mg（4），Ca（5）]。复合物的固态结构1，3和4通过单晶X射线衍射分析来建立。碱金属和碱土金属配合物1-5被
• Cellular Stress Upregulates Indole Signaling Metabolites in Escherichia coli
  作者：Chung Sub Kim、Jhe-Hao Li、Brenden Barco、Hyun Bong Park、Alexandra Gatsios、Ashiti Damania、Rurun Wang、Thomas P. Wyche、Grazia Piizzi、Nicole K. Clay、Jason M. Crawford

  DOI：10.1016/j.chembiol.2020.03.003

  日期：2020.6

  Escherichia coli broadly colonize the intestinal tract of humans and produce a variety of small molecule signals. However, many of these small molecules remain unknown. Here, we describe a family of widely distributed bacterial metabolites termed the "indolokines." In E. coli, the indolokines are upregulated in response to a redox stressor via aspC and tyrB transaminases. Although indolokine 1 represents a previously unreported metabolite, four of the indolokines (2-5) were previously shown to be derived from indole-3-carbonyl nitrile (ICN) in the plant pathogen defense response. We show that the indolokines are produced in a convergent evolutionary manner relative to plants, enhance E coli persister cell formation, outperform ICN protection in an Arabidopsis thaliana-Pseudomonas syringae infection model, trigger a hallmark plant innate immune response, and activate distinct immunological responses in primary human tissues. Our molecular studies link a family of cellular stress-induced metabolites to defensive responses across bacteria, plants, and humans.