pyrrole magnesium chloride

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: pyrrole magnesium chloride
• 英文别名: magnesium chloride pyrool-1-ide；Pyrrolmagnesiumchlorid；pyrrol-1-ylmagnesium chloride；Magnesium;pyrrol-1-ide;chloride；magnesium;pyrrol-1-ide;chloride
• 化学式: C₄H₄N*Cl*Mg
• 分子量: 125.84
• InChiKey: YZUTWJDHXYNRFI-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.73
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  pyrrole magnesium chloride 、 (S)-(+)-4-dibenzylamino-γ-lactone 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.5h， 以59%的产率得到(S)-3-dibenzylamino-4-hydroxypyrrol-1-ylbutan-1-one
  参考文献：
  名称：

  Practical ex-chiral-pool methodology for the synthesis of dopaminergic tetrahydroindoles

  摘要：

  Chemo- and regioselective transformations of asparagine gave access to optically active 5- and 6-amino tetrahydroindolizines when the 3-aminobutyrolactone (S)-2 was employed as a key intermediate. The target compounds were approached by a sequential and regiocontrolled bis-electrophilic attack in the positions 2 and 3 of the pyrrole ring system. Receptor binding experiments showed stereocontrolled receptor recognition leading to the D3 selective agonist (S)-8 with D3 binding that is comparable to the natural neurotransmitter dopamine. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.041

文献信息

• The Absolute Configuration of the Pyrrolosesquiterpenoid Glaciapyrrol A
  作者：Ramona Riclea、Jeroen S. Dickschat

  DOI：10.1002/chem.201101139

  日期：2011.10.10

  unambiguously clarified the relative configuration of natural glaciapyrrol A that was previously only partly solved from the available NMR data. An enantioselective synthesis was carried out resulting in the unnatural enantiomer (11S,12R,15R)‐(−)‐glaciapyrrol A. These data establish the absolute configuration of the natural product as (11R,12S,15S)‐(+)‐glaciapyrrol A.

  由Macherla等人从海洋链霉菌中分离得到的结构独特且具有中等细胞毒性的吡咯糖，半萜类化合物glaciapyrrol A的总合成物。Stark及其同事先前报道，使用已知的非对映选择性Ru催化方法合成四氢呋喃，分别从香叶醇或神经醇中制得1种和7种立体异构体。5比较的1 H和13个C NMR数据明确地阐明，先前仅部分地从可用的NMR数据解决自然glaciapyrrol A的相对构型。进行对映选择性合成，得到非天然对映异构体（11 S，12 R，15R）-（-）-glaciapyrrol A.这些数据确定了天然产物的绝对构型为（11 R，12 S，15 S）-（+）-glaciapyrrol A.
• A convergent general synthetic protocol for construction of spirocyclic ketal ionophores: an application to the total synthesis of (-)-A-23187 (calcimycin)
  作者：Robert K. Boeckman、Andre B. Charette、Theodros Asberom、Brian H. Johnston

  DOI：10.1021/ja00258a063

  日期：1987.11

  trimethyl-3,5,5' spirobi-2:2'-pyrane via la reaction du dihydro-3,4 methoxymethoxymethyl-1' ethyl-2 methyl-3 pyranne avec le bromo-1 t-butyldimethylsiloxy-4 t-butyldiphenylsiloxy-6 methyl-3 hexane. Application a la synthese de la calcimycine

  合成这些去叔丁基二苯基甲硅烷氧基-2″乙基-6'[羟甲基-1'乙基]-6全氢三甲基-3,5,5'螺双-2:2'-吡喃经由la反应二氢-3,4甲氧基甲氧基甲基-1 ' 乙基-2 甲基-3 吡喃 avec le bromo-1 t-丁基二甲基甲硅烷氧基-4 t-丁基二苯基甲硅烷氧基-6 甲基-3 己烷。应用a la 合成de la calcimycine
• Divalent Transition-Metal-Ion Stress Induces Prodigiosin Biosynthesis in<i>Streptomyces coelicolor</i>M145: Formation of Coeligiosins
  作者：Anne Morgenstern、Christian Paetz、Anne Behrend、Dieter Spiteller

  DOI：10.1002/chem.201405733

  日期：2015.4.13

  LC‐MS analysis revealed that in the red phenotype the production of the prodigiosins, undecylprodigiosin and streptorubin B, was strongly induced and, in addition, several intense signals appeared in the LC‐MS chromatogram. Using LC‐MS/MS and NMR spectroscopy, two new prodigiosin derivatives were identified, that is, coeligiosin A and B, which contained an additional undecylpyrrolyl side chain attached

  Coelicolor M145链霉菌细菌对过渡金属离子胁迫具有多种生长反应，导致不同的表型。特别是在存在Co 2+离子（0.7 m M）的情况下，天蓝色链霉菌始终产生红色表型。与野生型相比，该表型在挥发性化合物以及高分子量次生代谢产物的产生方面有很大差异。LC-MS分析显示，在红色表型中，强烈诱导了原黄酮素，十一烷基原黄酮素和链霉菌素B的产生，此外，LC-MS色谱图中还出现了一些强烈的信号。使用LC-MS / MS和NMR光谱法，鉴定出了两种新的prodigiosin衍生物，即腔肠球菌素A和B，其中包含一个附加的十一烷基吡咯烷基侧链，连接到十一烷基prodigiosin或链霉菌素B的三吡咯环系统的中心碳上。
• Generation of Penems, Carbapenems and Aza Analogs of Cephems by the Addition of Heterocycles and Other Building Blocks to Azetinones
  作者：Harry H. Wasserman、Mingde Xia、Andrew J. Carr、William T. Han、Miles G. Siegel

  DOI：10.1016/s0040-4020(00)00411-7

  日期：2000.7

  Addition of nucleophiles including heterocycles and precursors of vicinal tricarbonyls to azetinones generates building blocks incorporating potential electrophilic centers. Oxidation of these products provides reactive carbonyl units suitably located for reaction with the β-lactam NH yielding bicyclic products of biological interest.

  将亲核试剂（包括杂环和邻近的三羰基化合物的前体）加到氮杂环丁酮中会生成包含潜在亲电中心的结构单元。这些产物的氧化提供了适合于与β-内酰胺NH反应的反应性羰基单元，从而产生了具有生物学意义的双环产物。
• Practical ex-chiral-pool methodology for the synthesis of dopaminergic tetrahydroindoles
  作者：Markus Bergauer、Harald Hübner、Peter Gmeiner

  DOI：10.1016/j.tet.2003.11.041

  日期：2004.1

  Chemo- and regioselective transformations of asparagine gave access to optically active 5- and 6-amino tetrahydroindolizines when the 3-aminobutyrolactone (S)-2 was employed as a key intermediate. The target compounds were approached by a sequential and regiocontrolled bis-electrophilic attack in the positions 2 and 3 of the pyrrole ring system. Receptor binding experiments showed stereocontrolled receptor recognition leading to the D3 selective agonist (S)-8 with D3 binding that is comparable to the natural neurotransmitter dopamine. (C) 2003 Elsevier Ltd. All rights reserved.