1,2-diiodooct-1-ene

• 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: 1,2-diiodooct-1-ene
• 英文别名: 1,2-diiodo-1-octene
• 化学式: C₈H₁₄I₂
• 分子量: 364.008
• InChiKey: DORLJZLPKUVWBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  10.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  1-辛炔 在 碘 、 Diphenylphosphine oxide 作用下， 以 氯仿 为溶剂， 生成 1,2-diiodooct-1-ene 、 2-iodo-1-octene
  参考文献：
  名称：

  Highly regioselective hydroiodination of terminal alkynes and silylalkynes with iodine and phosphorus reagents leading to internal iodoalkenes

  摘要：

  Markovnikov-type hydroiodination of terminal alkynes with iodine and Ph2P(O)H took place selectively to afford the corresponding internal iodoalkenes in good yields. Combination of (PhO)(2)P(O)H and Ph2P(O)OH instead of Ph2P(O)H also provided internal iodoalkenes in excellent yields. This hydroiodination is advantageous in terms of mild conditions, convenient operation, and tolerance to various functional groups. In addition, direct synthesis of internal iodoalkenes from silylalkynes was also achieved by using a mixed system of iodine and phosphorus reagents. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.096

文献信息

• Direct Iodination of Monosubstituted Aryl Acetylenes and Acetylenic Ketones
  作者：Ling‐Guo Meng、Pei‐Jie Cai、Qing‐Xiang Guo、Song Xue

  DOI：10.1080/00397910701749724

  日期：2008.1

  Abstract Monosubstituted acetylenes were iodinated to form iodoacetylenes under simple conditions. Reaction of aryl acetylenes with molecular iodine in the presence of 4‐dimethylaminopyridine (DMAP) gave the desired products in good to excellent yields. Iodination of aryl acetylenic ketones using K2CO3 as base was also described.

  摘要 单取代的乙炔在简单的条件下被碘化形成碘乙炔。芳基乙炔与分子碘在 4-二甲氨基吡啶 (DMAP) 存在下反应，以良好至极好的收率得到所需产物。还描述了使用 K2CO3 作为碱对芳基炔酮进行碘化。
• Copper-Catalyzed 1,2-Addition of α-Carbonyl Iodides to Alkynes
  作者：Tao Xu、Xile Hu

  DOI：10.1002/anie.201410279

  日期：2015.1.19

  Abstractβ,γ‐Unsaturated ketones are an important class of organic molecules. Herein, copper catalysis has been developed for the synthesis of β‐γ‐unsaturated ketones through 1,2‐addition of α‐carbonyl iodides to alkynes. The reactions exhibit wide substrate scope and high functional group tolerance. The reaction products are versatile synthetic intermediates to complex small molecules. The method was applied for the formal synthesis of (±)‐trichostatin A, a histone deacetylase inhibitor.
• 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.
• Highly regioselective hydroiodination of terminal alkynes and silylalkynes with iodine and phosphorus reagents leading to internal iodoalkenes
  作者：Shin-ichi Kawaguchi、Haruna Masuno、Motohiro Sonoda、Akihiro Nomoto、Akiya Ogawa

  DOI：10.1016/j.tet.2012.08.096

  日期：2012.11

  Markovnikov-type hydroiodination of terminal alkynes with iodine and Ph2P(O)H took place selectively to afford the corresponding internal iodoalkenes in good yields. Combination of (PhO)(2)P(O)H and Ph2P(O)OH instead of Ph2P(O)H also provided internal iodoalkenes in excellent yields. This hydroiodination is advantageous in terms of mild conditions, convenient operation, and tolerance to various functional groups. In addition, direct synthesis of internal iodoalkenes from silylalkynes was also achieved by using a mixed system of iodine and phosphorus reagents. (c) 2012 Elsevier Ltd. All rights reserved.