4-(1-phenylundec-2-yn-1-yl)morpholine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(1-phenylundec-2-yn-1-yl)morpholine
• 英文别名: 4-(1-Phenylundec-2-ynyl)morpholine；4-(1-phenylundec-2-ynyl)morpholine
• 化学式: C₂₁H₃₁NO
• 分子量: 313.483
• InChiKey: RYCJFSGUYFWPIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(1-phenylundec-2-yn-1-yl)morpholine 在 zinc(II) iodide 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 1-phenylundeca-1,2-diene
  参考文献：
  名称：

  Mild-Condition Synthesis of Allenes from Alkynes and Aldehydes Mediated by Tetrahydroisoquinoline (THIQ)

  摘要：

  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.

  DOI：

  10.1021/jo4018183
• 作为产物：
  描述：

  吗啉 、 1-癸炔 、 苯甲醛 在 copper(l) iodide 、 丁二酸 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以86%的产率得到4-(1-phenylundec-2-yn-1-yl)morpholine
  参考文献：
  名称：

  CuI催化的琥珀酸三组分偶联反应简单经济地合成炔丙胺

  摘要：

  开发了一种实用有效的方法，以CuI为催化剂，以琥珀酸为添加剂，通过一锅法从醛，胺和炔烃合成炔丙基胺。通过使用此协议，可以高收率获得各种炔丙基胺。

  DOI：

  10.1071/ch08086

文献信息

• A Simple and Economic Synthesis of Propargylamines by CuI-Catalyzed Three-Component Coupling Reaction with Succinic Acid as Additive
  作者：Gerui Ren、Jinli Zhang、Zheng Duan、Mengjun Cui、Yangjie Wu

  DOI：10.1071/ch08086

  日期：——

  A practical and efficient method was developed for the synthesis of propargylamines in a one-pot procedure from aldehydes, amines, and alkynes by using CuI as catalyst and succinic acid as additive. By using this protocol, a wide range of propargylamines was obtained in high yields.

  开发了一种实用有效的方法，以CuI为催化剂，以琥珀酸为添加剂，通过一锅法从醛，胺和炔烃合成炔丙基胺。通过使用此协议，可以高收率获得各种炔丙基胺。
• Zn(OAc)2·2H2O: a versatile catalyst for the one-pot synthesis of propargylamines
  作者：Enugala Ramu、Ravi Varala、Nuvula Sreelatha、Srinivas R. Adapa

  DOI：10.1016/j.tetlet.2007.07.196

  日期：2007.10

  An inexpensive and readily available catalyst, Zn(OAc)(2)center dot 2H(2)O is successfully evaluated for effective one-pot synthesis of propargylamines with moderate to excellent yields for most of the substrates screened, without the need of base, co-catalyst or additive in the presence of air. (C) 2007 Elsevier Ltd. All rights reserved.
• Study on the A3-coupling reaction catalyzed by readily available copper-containing minerals. Synthesis of propargylamines
  作者：Mátyás Milen、Gábor Györke、András Dancsó、Balázs Volk

  DOI：10.1016/j.tetlet.2019.151544

  日期：2020.3

  The highly atom efficient three-component reaction of aldehydes, secondary amines and acetylenes to form propargylamines (A(3)-coupling) has been studied with twelve readily available copper-containing minerals. It was found that the reaction could easily be performed in the presence of malachite, brochantite, chrysocolla and azurite in toluene at reflux. The desired products were obtained in good to excellent yields. (C) 2019 Elsevier Ltd. All rights reserved.
• 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.