1-iodo-1-pentene | 1226376-51-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 1-iodo-1-pentene
• 英文别名: 1-Iodopent-1-ene
• CAS: 1226376-51-7
• 化学式: C₅H₉I
• 分子量: 196.031
• InChiKey: BKPFTDPOCSONMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  1-iodo-1-pentene 在 四(三苯基膦)钯 、 三正丁基氢锡 、 lead(IV) tetraacetate 、 溶剂黄146 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 50.67h， 生成
  参考文献：
  名称：

  Formal Intramolecular (4 + 1)-Cycloaddition of Dialkoxycarbenes: Control of the Stereoselectivity and a Mechanistic Portrait

  摘要：

  The stereoselective synthesis of 5-5, 6-5, and 7-5 fused O-heterocyclic compounds is reported. The key reaction is a formal intramolecular (4 + 1)-cycloaddition involving a dialkox-ycarbene and an electron-deficient diene where the stereo-selectivity is dependent on the length of the tether. An analysis of the stereochemical outcome of this reaction sheds light on its complex mechanistic picture. High-level calculations were used to support the proposed mechanistic portrait.

  DOI：

  10.1021/ja211927b

文献信息

• Diastereoselective Addition of Prochiral Nucleophilic Alkenes to α-Chiral <i>N</i>-Sulfonyl Imines
  作者：David A. Gutierrez、James Fettinger、K. N. Houk、Kaori Ando、Jared T. Shaw

  DOI：10.1021/acs.orglett.1c04219

  日期：2022.2.11

  to chiral α-alkoxy N-tosyl imines is described. Alkene geometry is selectively transferred to the newly formed carbon–carbon bond, resulting in stereochemical control of C1, C2, and C3 of the resulting 2-alkoxy-3-N-tosyl-4-alkyl-5-hexene products. A computational analysis to elucidate the high selectivity is also presented. This methodology was employed in the synthesis of two naturally occurring isomers

  描述了路易斯酸促进前手性E-和Z-烯丙基亲核试剂与手性 α-烷氧基N-甲苯磺酰基亚胺的加成。烯烃几何结构选择性地转移到新形成的碳-碳键上，从而对所得 2-烷氧基-3- N-甲苯磺酰基-4-烷基-5-己烯产物的 C1、C2 和 C3 进行立体化学控制。还提出了阐明高选择性的计算分析。该方法用于合成两种天然存在的硫磺酰胺异构体。
• Cross-coupling Reaction of β,β-Difluoro-α-phenylvinylstannane with Alkenyl Iodides: Novel Approach to 2-Phenyl-1,1-difluoro-1,3-butadienes
  作者：Ji-Hoon Choi、Kamaldeep Paul、Yeon-Hui Jung、In-Howa Jeong

  DOI：10.5012/bkcs.2010.31.01.025

  日期：2010.1.20

  interested in the straightforward method for the synthesis of 1,1-difluoro- 1,3-butadienes from the cross-coupling reaction of 2,2-diflu-oroalkenylmetal reagent with alkenyl halides, which should be a simple and efficient method. Palladium-catalyzed cross- coupling reactions of 1,1-difluorohomoallenyl bromide with aryl bromides and iodides and aryl boronic acids provided the corresponding 1,1-difluoro-1,3-butadienes

  然而，我们对通过 2,2-二氟-口烯基金属试剂与烯基卤化物的交叉偶联反应合成 1,1-二氟-1,3-丁二烯的直接方法感兴趣，这应该是一种简单有效的方法。方法。1,1-二氟高烯丙基溴与芳基溴化物和碘化物以及芳基硼酸的钯催化交叉偶联反应提供了相应的1,1-二氟-1,3-丁二烯。
• Total Synthesis of Pyrrolidine and Piperidine Natural Products via TMSOTf-Mediated “5/6-<i>endo-dig</i>” Reductive Hydroamination of Enynyl Amines
  作者：Santosh J. Gharpure、Raj K. Patel、Krishna S. Gupta

  DOI：10.1021/acs.orglett.3c02115

  日期：2023.8.11

  acid-mediated 5/6-endo-dig reductive hydroamination cascade of enynyl amines. The brevity of the developed strategy allowed for the collective stereoselective total synthesis of various alkaloids, including (±)-pyrrolidine cis-225H, (±)-epi-197B, (±)-epi-225C, the family of (+)-solenopsins and (+)-isosolenopsins, and the formal synthesis of (±)-bgugaine and (+)-azimic acid.

  带有疏水链的吡咯烷和哌啶的立体选择性合成已经通过烯炔胺的无金属、路易斯酸介导的5/6-内位还原氢胺化级联实现。所开发策略的简洁性允许集体立体选择性全合成各种生物碱，包括(±)-吡咯烷顺式-225H、(±)- epi -197B、(±)- epi -225C、(+)-家族Solenopins 和 (+)-isosolenopsins，以及 (±)-bgugaine 和 (+)-azimic Acid 的正式合成。
• Whole Structure−Activity Relationships of the Fat-Accumulation Inhibitor (−)-Ternatin: Recognition of the Importance of Each Amino Acid Residue
  作者：Kenichiro Shimokawa、Yoshiaki Iwase、Ryoka Miwa、Kaoru Yamada、Daisuke Uemura

  DOI：10.1021/jm800741n

  日期：2008.10.9

  A series of Ala and Aoc analogues of (-)-ternatin were prepared, and their bioactivities were assessed by a fat-accumulation inhibition assay using 3T3-L1 adipocytes, which led to the discovery of key structure-activity relationships (SAR).