2,5-diiodopent-1-ene | 110243-54-4

• 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: 2,5-diiodopent-1-ene
• CAS: 110243-54-4
• 化学式: C₅H₈I₂
• 分子量: 321.928
• InChiKey: XQDRCMPFKOIKTL-UHFFFAOYSA-N

物化性质

• 沸点：
  216.6±33.0 °C(Predicted)
• 密度：
  2.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  2,5-diiodopent-1-ene 在 palladium diacetate 、 sodium hydride 、 potassium carbonate 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 26.25h， 生成 9-methylene-6,7,8,9-tetrahydropyrido[1,2-a]indole
  参考文献：
  名称：

  1—Azatriene cyclisation as a route to annelated pyrido[4,3- b ]indoles

  摘要：

  Derivatives of indole-3-carbaldehyde oxime have been prepared that bear a carbon-carbon double bond at C-2 and a five- or six-membered ring linking the alpha-carbon artom of the vinyl group and the indole nitrogen atom. Compound 9, with a five-membered ring linking the two atoms, failed to undergo a cyclisation reaction on heating. However the oximes 16 and 22, with a six-memberd ring linking the two atoms. cyclised in boiling toluene. The cyclisation led to the formation of the pyrido-indoles 17 and 18, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00117-8
• 作为产物：
  描述：

  5-碘-1-戊炔 在 三甲基氯硅烷 、 水 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以85%的产率得到2,5-diiodopent-1-ene
  参考文献：
  名称：

  A Stille cyclisation approach to (−)-periplanone-B: studies in alkene-selective ring-closing metathesis and an improved chromium(II)-mediated synthesis of (E )-alkenylstannanes from aldehydes

  摘要：

  描述了一种通过高效的分子内Stille交叉耦合反应合成dienone 7，利用Bu3SnCHI2在DMF中改进的铬(II)介导的合成(E)-烯丙基锡化合物的反应，以及通过环闭合烯烃重排合成取代的(–)-dienone 25，得到二氢吡喃22。(–)-dienone 25的合成构成了(–)-periplanone-B的正式合成。

  DOI：

  10.1039/a905560f

文献信息

• Synthesis of Medium-Ring Nitrogen Heterocycles via Palladium-Catalyzed Heteroannulation of 1,2-Dienes
  作者：Richard C. Larock、Chi Tu、Paola Pace

  DOI：10.1021/jo980516p

  日期：1998.10.1

  nitrogen heterocycles are readily prepared by the palladium-catalyzed heteroannulation of a variety of 1,2-dienes by a range of tosylamide- and amine-containing aryl and vinylic halides. The ease of ring formation is seven > eight > nine, and better results are obtained using aryl halides, rather than vinylic halides, and tosylamide functionality, rather than amine functionality. The reaction is suggested

  七，八和九元环氮杂环很容易通过钯催化的各种1,2-二烯的杂芳环化反应，通过一系列含甲苯磺酰胺和胺的芳基和乙烯基卤化物来制备。形成环的难易程度是7> 8> 9，使用芳基卤化物而不是乙烯基卤化物和甲苯磺酰胺官能团而不是胺官能团可获得更好的结果。建议该反应通过将芳基或乙烯基钯化合物形成并添加到丙二烯中以产生π-烯丙基钯中间体而进行，该中间体随后在π-烯丙基系统的受阻较小的末端进行钯的亲核置换。
• Highly Selective Hydroiodation of Alkynes Using an Iodine−Hydrophosphine Binary System
  作者：Shin-ichi Kawaguchi、Akiya Ogawa

  DOI：10.1021/ol1005246

  日期：2010.5.7

  A novel hydroiodation of alkynes (1) using an iodine/hydrophosphine binary system takes place regioselectively to provide the corresponding Markovnikov-type adducts (2) in good yield. This hydroiodation is advantageous in terms of mild conditions, convenient operation, and tolerance to various functional groups.
• Piers, Edward, Pure and Applied Chemistry, 1988, vol. 60, p. 107 - 114
  作者：Piers, Edward

  DOI：——

  日期：——
• J. ORG. CHEM., 52,(1987) N 19, 4421-4423
  作者：

  DOI：——

  日期：——
• 1—Azatriene cyclisation as a route to annelated pyrido[4,3- b ]indoles
  作者：Thomas L. Gilchrist、Paul D. Kemmitt、Andrew L. Germain

  DOI：10.1016/s0040-4020(97)00117-8

  日期：1997.3

  Derivatives of indole-3-carbaldehyde oxime have been prepared that bear a carbon-carbon double bond at C-2 and a five- or six-membered ring linking the alpha-carbon artom of the vinyl group and the indole nitrogen atom. Compound 9, with a five-membered ring linking the two atoms, failed to undergo a cyclisation reaction on heating. However the oximes 16 and 22, with a six-memberd ring linking the two atoms. cyclised in boiling toluene. The cyclisation led to the formation of the pyrido-indoles 17 and 18, respectively. (C) 1997 Elsevier Science Ltd.