trans-2-hexenyl iodide | 115977-54-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机碘化物
• 英文名称: trans-2-hexenyl iodide
• 英文别名: trans-1-iodo-2-hexene；trans-1-iodohex-2-ene；(2E)-1-iodo-2-hexene；(E)-1-iodo-hex-2-ene；(E)-2-Hexenyl iodide；(E)-1-iodo-2-hexene；1-Iodohex-2-ene；(E)-1-iodohex-2-ene
• CAS: 115977-54-3
• 化学式: C₆H₁₁I
• 分子量: 210.058
• InChiKey: SHZUPNQWZAHROG-SNAWJCMRSA-N

物化性质

• 沸点：
  172.5±9.0 °C(Predicted)
• 密度：
  1.500±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  trans-2-hexenyl iodide 在 sodium tetrahydroborate 、 正丁基锂 、 苯基溴化硒 、 二苯基二硒醚 、 二甲基二环氧乙烷 、 二正丁基氧化锡 、 苯基硒基三氟甲烷磺酸酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 105.92h， 生成 (4S,5R)-4-[(2S,5S,6S)-5,6-diphenyl-1,4-dioxan-2-yl]-5-ethenyl-1,3-dioxolan-2-one
  参考文献：
  名称：

  使用（S，S）-氢安息香素作为手性来源，由简单的非手性烯丙基卤化物合成（+）-聚草酰胺酸和D-山梨醇。

  摘要：

  顺式-1-溴-2-戊烯与（S，S）-氢苯偶姻亚锡缩醛的偶合反应，然后对所得烯丙基醚进行区域和立体选择性转化，得到（+）-聚草酰胺酸，并采用相似的方法合成来自反式-1-碘-2-己烯的D-山梨醇。

  DOI：

  10.1039/b202823a
• 作为产物：
  描述：

  (E)-hex-4-en-1-yl 4-methylbenzenesulfonate 在 sodium iodide 作用下， 以 丙酮 为溶剂， 以85%的产率得到trans-2-hexenyl iodide
  参考文献：
  名称：

  Regiochemical and stereochemical studies on halocyclization reactions of unsaturated sulfides

  摘要：

  The regiochemistry and stereochemistry for the halocyclization reactions of unsaturated benzyl sulfides have been examined as a function of tether length, type of unsaturation (carbon-carbon double bond versus carbon-carbon triple bond), substituents, and halogenating agent. Alkenyl sulfides were found to react with iodine or bromine at room temperature to give five-membered ring cycloadducts exclusively over those having four-membered rings, while for larger systems, six-membered ring products are formed preferentially over their five-membered ring isomers and exclusively over the seven-membered ring adducts. The endo- versus exo-regioselectivity of these alkenyl sulfide ring closures most likely reflects the difference in thermodynamic stabilities of the beta-halo sulfide cycloadducts, which are able to equilibrate via a common episulfonium intermediate. The efficiency of the cyclization process markedly drops off for these alkenyl sulfides as the tether length increases beyond four intervening carbon centers. Thus, while the halogenations of 3-butenyl sulfides and 4-pentenyl sulfides give high yields of cycloadducts, those of 5-hexenyl sulfides afford only small amounts of cyclized products and large quantities of acyclic dibromides. Conversely the reactions of acetylenic sulfides with iodine give uniformly high yields and regiochemical control regardless of the tether length. Thus, 3-butynyl and 4-pentynyl sulfides cyclize cleanly to the five-membered ring while 5-hexynyl sulfides give exclusively the six-membered ring, The products arising from these alkynyl sulfide ring closures are believed to be formed under kinetic control. The methodology has been applied to the synthesis of unusual bicyclic beta-lactams related to the penicillin family of antibiotics.

  DOI：

  10.1021/jo00125a038

文献信息

• Regiospezifische Herstellung von primären Allylacetaten (2-Alkenyl-acetaten)
  作者：Antonio García Martínez、Angeles Cruces Villalobos、Manuel Oliver Ruiz

  DOI：10.1055/s-1988-27464

  日期：——

  Regiospecific Preparation of Primary Allyl Acetates (2-Alkenyl Acetates) The reaction of primary, secondary and tertiary allyl alcohols 1 with anhydrous magnesium iodide in benzene gives regiospecifically the primary allyl iodides 2. The corresponding primary allyl acetates 3 are obtained regiospecifically by reaction of 2 with anhydrous sodium acetate in dimethylformamide.

  一级烯丙基乙酸酯（2-烯基乙酸酯）的区域特异性制备方法： 一级、二级和三级烯丙醇1与无水碘化镁在苯中反应，区域特异性生成一级烯丙基碘2。通过2与无水醋酸钠在二甲基甲酰胺中的反应，可以同样区域特异性地获得相应的一级烯丙基乙酸酯3。
• A Convenient One Pot Allylation of Aldehydes with Allylic Halides Prepared in Situ from Allylic Alcohols in the Presence of Metallic Bismuth
  作者：Norikazu Miyoshi、Mami Nishio、Shunsuke Murakami、Tomohiro Fukuma、Makoto Wada

  DOI：10.1246/bcsj.73.689

  日期：2000.3

  A convenient one pot allylation of aldehydes with allylic iodides prepared in situ from allylic alcohols by using trimethylsilyl chloride and sodium iodide proceeds smoothly in the presence of meta...

  醛与烯丙基碘的方便的单锅烯丙基化反应，在间苯二甲酸存在下，使用三甲基氯硅烷和碘化钠由烯丙醇原位制备。
• Thione Esters as Substrates for the Stereoselective Alkylation of Model Compounds of Nonactic Acids
  作者：François Loiseau、Inga Kholod、Reinhard Neier

  DOI：10.1002/ejoc.200901513

  日期：2010.8

  relative configurations could be achieved. In the third route the thione ester 18 was deprotonated with tBuOK. At temperatures below -78 °C, the enolate maintained the cis configuration of the substituents at the tetrahydrofuran ring. The alkylated product 12 could be isolated with a satisfactory cis/trans ratio of 85:15. The model compound 12 could be successfully transformed into more hydrophobic derivatives

  天然存在的macrotetrolide 抗生素nonactin 用于铵离子选择性电极。为了增加这些传感器半透膜中非肌动蛋白的寿命，我们开发了引入疏水侧链的方法。合成了非乳酸的简单模型化合物，例如 5 和 7。在 2,5-二取代四氢呋喃中保持取代基的顺式排列被证明是困难的。研究了三种不同的路线。通过用 NaHMDS 或 KHMDS 处理获得的烯醇化物可以用苄基或烯丙基碘作为亲电子试剂进行烷基化。在这些条件下，四氢呋喃环上的取代基发生顺式/反式异构化。开发了一种多步骤方法作为合成替代方案。该序列由选择性逆迈克尔反应组成，5-exo-tet 碘环化和自由基取代。通过两种方法获得的产品可以相关联，从而可以实现相对配置的暂定分配。在第三条路线中，硫酮酯 18 用 tBuOK 去质子化。在低于 -78 °C 的温度下，烯醇保持四氢呋喃环上取代基的顺式构型。可以以85:15的令人满意的顺/反比分离烷基化产物12。通过使用
• One-Pot Synthesis of Homoallylic Alcohols via a Facile Conversion of Allylic Alcohols into Allylic Iodides
  作者：Takaya Kanai、Shinji Irifune、Yasutaka Ishii、Masaya Ogawa

  DOI：10.1055/s-1989-27223

  日期：——

  Allylic alcohols were readily converted into allylic iodides by hydrogen iodide generated in situ from chlorotrimethylsilane/sodium iodide and water, or alcohols, under mild conditions. Displacement of allylic alcohols containing a terminal double bond gave allylic iodides accompanied by allylic rearrangement. This procedure has successfully been extended to a one-pot synthesis of homoallylic alcohols by carrying out successive Barbier type reactions.

  烯丙醇在温和条件下通过氯三甲基硅烷/碘化钠和水或醇现场生成的氢碘酸，可以方便地转化为烯丙基碘化物。具有末端双键的烯丙醇的取代反应会产生伴随烯丙基重排的烯丙基碘化物。这一方法已成功扩展为通过连续的巴比耶型反应，实现高烯丙醇的一锅法合成。
• A Facile Synthesis of Alkyl Iodides and Deuterated Alkyl Iodides by Hydroiodination and Deuterioiodination of Olefins
  作者：Shinji Irifune、Takao Kibayashi、Yasutaka Ishii、Masaya Ogawa

  DOI：10.1055/s-1988-27575

  日期：——

  Chlorotrimethylsilane/sodium iodide in the presence of water has been found as facile method for the hydroiodination of olefins to alkyl iodides under mild conditions. This procedure has successfully been extended to the preparation of deuterated alkyl iodides by using deuterium oxide in place of water.

  在水存在下，发现氯三甲基硅烷/碘化钠为一种简便方法，可在温和条件下实现烯烃的氢碘化反应生成烷基碘。通过使用重水代替普通水，这一方法已成功扩展到制备氘化的烷基碘。