| 1431291-41-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1431291-41-6
• 化学式: C₁₈H₂₆
• 分子量: 242.404
• InChiKey: VJGSAIFYIKJRKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  3-甲基苯甲醛 在 copper(I) bromide 、 zinc(II) iodide 作用下， 以 甲苯 为溶剂， 反应 39.0h， 生成
  参考文献：
  名称：

  使用2-二烷基氨基甲基吡咯烷，醛类和1-炔烃的卤化铜（I）促进手性炔丙基胺和手性烯丙基的非对映选择性合成

  摘要：

  在25°C下，溴化铜促进醛，1-炔烃和手性2-二烷基氨基甲基吡咯烷的反应，可以以高达96％的收率和99：1 dr的速率得到相应的手性炔丙基胺衍生物，这些衍生物很容易转化为相应的被破坏的手性丙二烯在100°C下与CuI在二恶烷中反应后，产率为81％，ee为99％。

  DOI：

  10.1021/jo302534f

文献信息

• Mild-Condition Synthesis of Allenes from Alkynes and Aldehydes Mediated by Tetrahydroisoquinoline (THIQ)
  作者：Guo-Jie Jiang、Qin-Heng Zheng、Meng Dou、Lian-Gang Zhuo、Wei Meng、Zhi-Xiang Yu

  DOI：10.1021/jo4018183

  日期：2013.12.6

  A practical 1,2,3,4-tetrahydroisoquinoline (THIQ)-mediated synthesis of 1,3-disubstituted allenes from terminal alkynes and aldehydes under mild conditions in the presence of CuBr first and then ZnI2 was reported. This telescoped allene synthesis reaction includes three consecutive steps and two reactions: first, a room-temperature CuBr-catalyzed synthesis of propargylamines, exo-yne-THIQs, from terminal alkynes, aldehydes, and THIQ then filtration of the CuBr catalyst, and finally the ZnI2-mediated allene synthesis from the generated exo-yne-THIQs under mild conditions (either at room temperature or heating at 50 or 75 degrees C). A wide range of aliphatic or aromatic aldehydes and terminal alkynes are tolerated, affording the allene products in up to 92% yield. Especially, temperature-sensitive aldehydes can be used in the reaction system. Preliminary exploration of the asymmetric allene synthesis has also been conducted, and a moderate enantioselectivity has been achieved. Finally, the relative reactivities of several secondary amines were compared with THIQ, showing that THIQ is the best of these amines in the synthesis of allenes under mild reaction conditions.
• Copper(I) Halide Promoted Diastereoselective Synthesis of Chiral Propargylamines and Chiral Allenes using 2-Dialkylaminomethylpyrrolidine, Aldehydes, and 1-Alkynes
  作者：Ramani Gurubrahamam、Mariappan Periasamy

  DOI：10.1021/jo302534f

  日期：2013.2.15

  Copper bromide promoted reactions of aldehydes, 1-alkynes, and chiral 2-dialkylaminomethylpyrrolidine at 25 °C give the corresponding chiral propargylamine derivatives in up to 96% yield and 99:1 dr that are readily converted to the corresponding disubstitued chiral allenes in up to 81% yield and 99% ee upon reaction with CuI in dioxane at 100 °C.

  在25°C下，溴化铜促进醛，1-炔烃和手性2-二烷基氨基甲基吡咯烷的反应，可以以高达96％的收率和99：1 dr的速率得到相应的手性炔丙基胺衍生物，这些衍生物很容易转化为相应的被破坏的手性丙二烯在100°C下与CuI在二恶烷中反应后，产率为81％，ee为99％。