(Z)-1-iodo-2-propyl-1,4-bis(trimethylsilyl)-1-buten-3-yne | 500791-53-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-1-iodo-2-propyl-1,4-bis(trimethylsilyl)-1-buten-3-yne
• 英文别名: [(Z)-1-iodo-2-(2-trimethylsilylethynyl)pent-1-enyl]-trimethylsilane
• CAS: 500791-53-7
• 化学式: C₁₃H₂₅ISi₂
• 分子量: 364.417
• InChiKey: LFYDZTIUSXDKPR-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  (Z)-1-iodo-2-propyl-1,4-bis(trimethylsilyl)-1-buten-3-yne 在 N-碘代丁二酰亚胺 、 copper(l) iodide 、 四(三苯基膦)钯 、 叔丁基锂 、 potassium carbonate 、 二乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 正戊烷 为溶剂， 反应 41.5h， 生成 (5E,9E)-10-Ethynyl-2-methyl-5,6,9-tripropyl-trideca-5,9-diene-3,7-diyn-2-ol
  参考文献：
  名称：

  Highly Practical and General Synthesis of Monodisperse Linear π-Conjugated Oligoenynes and Oligoenediynes with Either trans- or cis-Olefin Configuration

  摘要：

  Efficient and practical synthesis of a variety of 1-iodo-4-(trimethylsilyl)but-1-en-3-yne derivatives 1 and 2 with trans- and cis-olefin configuration was described. Their repeated use as building blocks allowed the facile synthesis of trans- and cis-oligoenynes, respectively. Development of a highly practical method for preparing monodisperse trans- and cis-oligoenediynes having the effective conjugation length was also accomplished by using 5 and 4, which can be readily prepared from 1 and 2, respectively.

  DOI：

  10.1021/ja037975e
• 作为产物：
  描述：

  1-三甲硅基-1-戊炔 在 四氢吡咯 、 titanium(IV) isopropylate 、 异丙基氯化镁 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 (Z)-1-iodo-2-propyl-1,4-bis(trimethylsilyl)-1-buten-3-yne
  参考文献：
  名称：

  Efficient and General Synthetic Method for Preparing Oligoenynes with Either trans- or cis-Olefinic Configuration

  摘要：

  Efficient and practical synthesis of a variety of 1-iodo-4-trimethylsilylbut-1-en-3-yne derivatives with trans- and cis-olefinic configuration, and their repeated use as building blocks for the synthesis of trans- and cis-oligoenynes, respectively, are described.

  DOI：

  10.1021/ol0274413

文献信息

• Synthesis and Optical Properties of all-<i>trans</i>-Oligodiacetylenes
  作者：Gregor S. Pilzak、Barend van Lagen、Cindy C. J. Hendrikx、Ernst J. R. Sudhölter、Han Zuilhof

  DOI：10.1002/chem.200800241

  日期：2008.9.8

  A new series of pure and highly soluble oligodiacetylenes (ODAs) was synthesized in high yield and on a multi-milligram scale by a sequence of Sonogashira reactions with a strongly reduced level of homocoupling. The lambda max and epsilon max of these ODAs show an increase with both chain elongation and solvent polarity. A plot of lambda max absorption versus 1/CL (CL=conjugation length) was shown

  通过一系列Sonogashira反应，均化水平大大降低，以高收率和数毫克级合成了一系列新的纯净和高度可溶性的低聚二乙炔（ODA）。这些ODA的λ最大和ε最大随着链伸长和溶剂极性的增加而增加。λ最大吸收量与1 / CL的关系图（CL =共轭长度）显示为线性。对于该系列中最长的成员，在微摩尔浓度下，λ最大值收敛至435 nm。这表明，对于PDA链观察到的最长的波长吸收（最大700 nm的λ）是由于聚集效应引起的。荧光量子产率从单体到三聚体增加，而对于更长的ODA则降低。在三聚体的最大荧光寿命中发现了类似的趋势，最大为600 ps。所观察到的旋转相关时间与低聚物长度的线性关系表明溶液中的ODA链缺乏明显的几何变化。这意味着溶液中的ODA是长度长达4 nm的完全拉伸的分子棒。
• Efficient and General Synthetic Method for Preparing Oligoenynes with Either <i>trans</i>- or <i>cis</i>-Olefinic Configuration
  作者：Yuuki Takayama、Christophe Delas、Kenji Muraoka、Fumie Sato

  DOI：10.1021/ol0274413

  日期：2003.2.1

  Efficient and practical synthesis of a variety of 1-iodo-4-trimethylsilylbut-1-en-3-yne derivatives with trans- and cis-olefinic configuration, and their repeated use as building blocks for the synthesis of trans- and cis-oligoenynes, respectively, are described.
• Highly Practical and General Synthesis of Monodisperse Linear π-Conjugated Oligoenynes and Oligoenediynes with Either <i>trans</i>- or <i>cis</i>-Olefin Configuration
  作者：Yuuki Takayama、Christophe Delas、Kenji Muraoka、Minoru Uemura、Fumie Sato

  DOI：10.1021/ja037975e

  日期：2003.11.1

  Efficient and practical synthesis of a variety of 1-iodo-4-(trimethylsilyl)but-1-en-3-yne derivatives 1 and 2 with trans- and cis-olefin configuration was described. Their repeated use as building blocks allowed the facile synthesis of trans- and cis-oligoenynes, respectively. Development of a highly practical method for preparing monodisperse trans- and cis-oligoenediynes having the effective conjugation length was also accomplished by using 5 and 4, which can be readily prepared from 1 and 2, respectively.