(Z)-3-溴-1-碘丙烯 | 220302-07-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 中文名称: (Z)-3-溴-1-碘丙烯
• 英文名称: 3-bromo-1-iodopropene
• 英文别名: 3-Bromo-1-iodoprop-1-ene
• CAS: 220302-07-8
• 化学式: C₃H₄BrI
• 分子量: 246.873
• InChiKey: NLKJYDMEZIZSKI-UHFFFAOYSA-N

物化性质

• 沸点：
  180.8±23.0 °C(Predicted)
• 密度：
  2.381±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  5
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  苯甲醛 、 (Z)-3-溴-1-碘丙烯 在 四(三苯基膦)钯 indium 、 碘苯 、 lithium chloride 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 25.0h， 以72%的产率得到1-苯基-3-丁烯-1-醇
  参考文献：
  名称：

  一种用烯丙基二铟试剂一锅法合成线性高烯丙醇的新级联反应

  摘要：

  开发了一种基于新型烯丙基二铟试剂的新级联反应；由 3-溴-1-碘丙烯制备的铟试剂在 Pd(0) 催化剂存在下依次与羰基化合物偶联，然后与芳基、烯基或烯丙基卤化物偶联，以提供方便的一锅法合成线性均烯丙醇。

  DOI：

  10.1039/b010176l
• 作为产物：
  描述：

  3-Iodo-2-propen-1-ol 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 (Z)-3-溴-1-碘丙烯
  参考文献：
  名称：

  A new route to 9,9a-Dihydro-3H-pyrrolo[1,2-a]indoles via radical cyclization

  摘要：

  A new method for the preparation of 9,9a-dihydro-3H-pyrrolo[1,2-a]indoles, an important substructure for the synthesis of mitomycins, is presented. A number of representative indoles are allylated on nitrogen with 1,3-dihalopropenes followed by n-Bu3SnH-mediated radical cyclization. The effect of the substitution patterns of the indoles and reaction conditions is explored. In all reactions the products of cyclization predominate; however, uncyclized materials are produced along with isomers and oxidation products of the cyclized substances.

  DOI：

  10.1021/jo00011a008

文献信息

• Reaction of indium ate complexes with allylic compounds. Controlling SN2/SN2′ selectivity by solvents
  作者：Tsunehisa Hirashita、Yousuke Hayashi、Kazuma Mitsui、Shuki Araki

  DOI：10.1016/j.tetlet.2004.02.129

  日期：2004.4

  giving a regioisomeric mixture of SN2 and SN2′ products. The ratio of SN2/SN2′ selectivity can be controlled by solvents; in the presence of polar solvents, such as N-butylpyrrolidone (NBP) and THF, the SN2′ product was mainly obtained, whereas the SN2 product was selectively prepared in solutions containing hexane. The vinylindium compound, generated by the reaction of allylic-type diindium reagents

  制备了乙烯基和甲基铟酸酯复合物（硬脂酸酯），并研究了向肉桂酰溴的迁移趋势和区域选择性。乙烯基组更优选大于Me基团转移，给出的S上的区域异构体混合物Ñ 2和S Ñ 2'的产品。S N 2 / S N 2'选择性的比率可以通过溶剂来控制。在极性溶剂（例如N-丁基吡咯烷酮（NBP）和THF）存在下，主要获得S N 2'产物，而S N在含有己烷的溶液中选择性制备2种产物。由烯丙基型二铟试剂与亚胺反应生成的乙烯基铟化合物也被转化为相应的乙烯基吲哚，使其与烯丙基氯反应，得到三组分偶联产物。
• Concise and Stereoselective Total Syntheses of Annotinolides C, D, and E
  作者：Pei Qu、Scott A. Snyder

  DOI：10.1021/jacs.1c05942

  日期：2021.8.11

  core bearing six contiguous stereocenters, including four that are fully substituted. Herein, we document a concise and stereoselective route that achieves the first total syntheses of three of its members: annotinolides C, D, and E. Key operations include a gold(I)-catalyzed Conia-ene reaction that fashions much of the main core in a single operation, as well as a number of other challenging and chemoselective

  annotinolides 是石松属植物的最新添加物之一生物碱家族，其成员具有具有挑战性的笼状结构，包括一个 [3.2.1]-双环核心，带有六个连续的立体中心，其中四个被完全取代。在此，我们记录了一种简洁且立体选择性的路线，该路线实现了其三个成员的首次全合成：annotinolides C、D 和 E。关键操作包括金（I）催化的 Conia-ene 反应，该反应形成了大部分主要核心在单个操作中，以及许多其他具有挑战性和化学选择性的转换以生成剩余的元素。此外，利用天然产物本身的努力，寻求调整其氧化态和单个环系统的重排，揭示了它们潜在的生物发生，并产生了一些与最初提出的结果相反的结果。最后，
• Catalytic Asymmetric Alkynylation of 3,4‐Dihydro‐β‐carbolinium Ions Enables Collective Total Syntheses of Indole Alkaloids
  作者：Lixin Liang、Shiqiang Zhou、Wei Zhang、Rongbiao Tong

  DOI：10.1002/anie.202112383

  日期：2021.11.15

  Catalytic asymmetric alkynylation of 3,4-dihydro-β-carbolinium ions was developed for the versatile synthesis of enantiomerically enriched C1-alkynyl tetrahydro-β-carbolines, the utility of which was demonstrated by concise collective total syntheses of the seven indole alkaloids harmicine, geissoschizol, geissoschizine, akuammicine, desethyleburnamonine, eburnamonine, and larutensine within 10 steps

  开发了 3,4-二氢-β-咔啉离子的催化不对称炔化作用，用于合成富含对映异构体的 C1-炔基四氢-β-咔啉，其效用已通过七种吲哚生物碱甘草碱的简明集体全合成证明， geissoschizol、geissoschizine、akuammicine、desethyleburnamonine、eburnamonine 和 larutensine 在 10 个步骤内（见方案）。
• Tandem Radical Cyclizations with Iodoaryl Azides:  Formal Total Synthesis of (±)-Aspidospermidine
  作者：Balaram Patro、John A. Murphy

  DOI：10.1021/ol006477x

  日期：2000.11.1

  An iodoazide radical cascade cyclization strategy has been used as the key step in a formal synthesis of aspidospermidine. Specifically, this step generated the alkaloid's B- and E-rings in the ethylidene-functionalized tetracycle 5. In turn, this was converted into pentacycle 25, a known advanced synthetic precursor of aspidospermidine.

  碘叠氮化物自由基级联环化策略已被用作阿斯哌啶的正式合成中的关键步骤。具体而言，该步骤在亚乙基官能化的四环五环5中生成了生物碱的B环和E环。然后，将其转化为五环二烯25，这是已知的先进的曲霉精的合成前体。
• Allylic-Type Diindium Reagents. Reactivity toward Electrophiles and Cascade Coupling Reactions with Imines
  作者：Tsunehisa Hirashita、Yousuke Hayashi、Kazuma Mitsui、Shuki Araki

  DOI：10.1021/jo026609v

  日期：2003.2.1

  The allylic-type diindium reagents A and B were prepared from 3-bromo-1-iodopropene (1a) and 4-bromo-2-iodobut-2-ene (1b), respectively, and their reactions with electrophiles were investigated. The diindium reagents A and B were initially reacted with imines and the resulting vinylindium compounds were then treated with organic halides in the presence of Pd(PPh3)(4) to give linear N-aryl and N-tosyl homoallylic amines. Diindium A is stable in a small amount of water in solvent, whereas B is easily protonated to give a crotylindium reagent. The reaction of B with benzaldehyde gives mainly the 1,3- and 1,5-diols via a spontaneous coupling with two molecules of the aldehyde, in contrast to A, which reacts with one molecule of carbonyl compounds to give the vinylindium compounds.