(E)-1-iodohepta-4,6-diene | 110027-81-1

• 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: (E)-1-iodohepta-4,6-diene
• 英文别名: (E)-1-iodo-4,6-heptadiene；(E)-7-iodohepta-1,3-diene；1-iodo-hepta-4(E),6-diene；1-iodo-4(E),6-heptadiene；1-iodohepta-4,6-diene；7-iodohepta-1,3-diene；(3E)-7-iodohepta-1,3-diene
• CAS: 110027-81-1
• 化学式: C₇H₁₁I
• 分子量: 222.069
• InChiKey: CSHBGYDHOHOAJV-ONEGZZNKSA-N

物化性质

• 沸点：
  192.2±19.0 °C(Predicted)
• 密度：
  1.464±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  (E)-1-iodohepta-4,6-diene 在 六甲基磷酰三胺 、 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.75h， 生成 (E)-6,8-nonadienol
  参考文献：
  名称：

  Stereochemical control in intramolecular Diels-Alder reactions with carbene complexes as ester synthons

  摘要：

  An evaluation of the intramolecular Diels-Alder reactions of Fischer carbene complexes was made for complexes which have an all-carbon tether between the diene and dienophile. Specifically, both the cis- and trans-isomers of the deca-2,7,9-trienyl carbene complexes (26-cis, 24-trans) and the undeca-2,8,10-trienyl carbene complexes (27-cis, 25-trans) were prepared and the rates and stereoselectivities of their intramolecular Diels-Alder reactions were in each case compared with those of the known reactions of their corresponding methyl esters. For the deca-2,7,9-trienyl complexes 24 and 26, the stereoselectivities are comparable to those observed for the Lewis-acid-catalyzed reactions of their corresponding methyl esters and much higher than the thermal reactions of the methyl esters which are completely unselective. The undeca-2,8,10-trienyl complex 25 undergoes intramolecular Diels-Alder reaction with a 93:7 endo/exo selectivity whereas the corresponding methyl ester 7 is known to give a 51:49 selectivity under thermal conditions and to fail with attempts at Lewis acid catalysis. The cis-substituted complex 27 also undergoes a selective reaction where the corresponding reaction of the ester fails. In addition no trace of isomerization of the cis-complex 27 could be observed during its cycloaddition. The triphenylphosphine and isopropoxy complexes 28-30 were prepared, and the stereoselectivity of their intramolecular Diels-Alder reactions is consistent with an s-trans conformation of the vinyl carbene funtionality in the transition state. In all cases the carbene complex cycloadducts can be oxidatively cleaved in high yield to their corresponding esters. The results show that the value of these complexes as synthons for esters is a result of tolerance of the carbene complex functional group to sensitive diene units which do not tolerate traditional Lewis acids utilized in accelerating intramolecular Diels-Alder reactions.

  DOI：

  10.1021/jo00061a008
• 作为产物：
  描述：

  (4E)-hepta-4,6-dien-1-ol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以76%的产率得到(E)-1-iodohepta-4,6-diene
  参考文献：
  名称：

  Synthesis of the A/E/F sections of conaconitine, napelline and related diterpenoid alkaloids of the aconitine group

  摘要：

  以戊-1,4-二烯-3-醇为原料，分别用八个步骤（总收率 20%）和九个步骤（总收率 16%）合成了三环胺 (±)-2；R = H 和 R = Me，具有五个立体中心，代表了标题生物碱的 A/E/F 环系统。

  DOI：

  10.1039/a804664f

文献信息

• Asymmetric intramolecular Diels-Alder reactions of N-acyl-camphor-sultam trienes.
  作者：Wolfgang Oppolzer、Dominique Dupuis

  DOI：10.1016/s0040-4039(00)98228-5

  日期：1985.1

  Treatment of triene-imides 4 with EtAlCl2 at −20° gave crystalline cycloadducts 5 which furnished enantiomerically pure bicyclic alcohols 9 with regeneration of the chiral auxiliary.

  在-20°下用EtAlCl 2处理三烯酰亚胺4，得到结晶的环加合物5，其提供对映体纯的双环醇9并具有手性助剂的再生。
• Generation and alkylation of 2-boryl allylic sulfone anions
  作者：Erich F. Altenhofer、Michael Harmata

  DOI：10.1039/c3cc00030c

  日期：——

  The deprotonation and electrophilic trapping of an allylic sulfone substituted at the 2 position by a pinacol boronate results in the formation of the corresponding alkylation products. The ability of the boronate ester to tolerate the sulfonyl carbanion suggests a broader application of the methodology to prepare a wide range of functionalized boronates.

  频哪醇硼酸酯在2位取代的烯丙基砜的去质子化和亲电子捕集导致形成相应的烷基化产物。硼酸酯耐受磺酰碳负离子的能力表明该方法在制备各种功能化硼酸酯方面的广泛应用。
• Preparation of 2-Alkyl- and 2-Acylpropenals from 5-(Trifluoromethanesulfonyloxy)-4H-1,3-dioxin: A Versatile Acrolein α-Cation Synthon
  作者：Stephen P. Fearnley、Raymond L. Funk、Robert J. Gregg

  DOI：10.1016/s0040-4020(00)00872-3

  日期：2000.12

  catalyzed cross-coupling reactions to provide 5-substituted-4H-1,3-dioxins 5. Upon thermolysis, these compounds undergo facile retrocycloaddition reactions to generate the corresponding 2-substituted acroleins which, if necessary, can be trapped in situ with dienes or heterodienophiles. In particular, the heretofore unknown 2-acylacroleins can be generated using this methodology and trapped with enol ethers

  5-（三氟甲磺酰氧基）-4 H -1,3-二恶英（3）参与各种与铜酸盐试剂的亲核取代反应，或参与钯催化的交叉偶联反应以提供5-取代的4 H -1,3-二恶英5。在热解后，这些化合物进行容易的逆转录加成反应以生成相应的2-取代的丙烯醛，如果需要的话，可以将其与二烯或异二烯体原位捕获。特别地，可以使用该方法产生迄今未知的2-酰基丙烯醛，并用烯醇醚捕集以提供5-酰基-3,4-二氢-2 H-吡喃（6g，h），这是许多天然产物共有的亚结构单元。
• A Palladium(II)-Catalyzed CH Activation Cascade Sequence for Polyheterocycle Formation
  作者：Stephen P. Cooper、Kevin I. Booker-Milburn

  DOI：10.1002/anie.201501037

  日期：2015.5.26

  Polyheterocycles are found in many natural products and are useful moieties in functional materials and drug design. As part of a program towards the synthesis of Stemona alkaloids, a novel palladium(II)‐catalyzed CH activation strategy for the construction of such systems has been developed. Starting from simple 1,3‐dienyl‐substituted heterocycles, a large range of polycyclic systems containing pyrrole

  多杂环存在于许多天然产物中，并且在功能材料和药物设计中是有用的部分。作为合成花粉生物碱的计划的一部分，已经开发了一种新型的钯（II）催化的CH活化策略来构建此类系统。从简单的1,3-二烯基取代的杂环开始，可以一步合成大量包含吡咯，吲哚，呋喃和噻吩部分的多环系统。
• Gold-catalyzed intramolecular hydroalkoxylation/cyclization of conjugated dienyl alcohols
  作者：B. Chandrasekhar、Jae-Sang Ryu

  DOI：10.1016/j.tet.2012.03.120

  日期：2012.6

  groups to tethered conjugated dienes are described. The reactions proceed smoothly at 60 °C in the presence of 5 mol % of (PPh3)AuCl/AgOTf as a catalyst. A broad range of structurally diverse conjugated dienes produce substituted tetrahydrofurans and tetrahydropyrans in good yields. This reaction represents an atom-economic route to construct five- and six-membered cyclic ethers.

  描述了羟基到束缚的共轭二烯的催化分子内加成。在5mol％的（PPh 3）AuCl / AgOTf作为催化剂的存在下，反应在60℃下顺利进行。多种结构多样的共轭二烯可以高产率产生取代的四氢呋喃和四氢吡喃。该反应代表构造五元和六元环状醚的原子经济路线。