N-cyclopropyldiphenylamine | 890534-61-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-cyclopropyldiphenylamine
• 英文别名: N,N-diphenylcyclopropylamine；N-cyclopropyl-N-phenylaniline；N,N-diphenylaminocyclopropane
• CAS: 890534-61-9
• 化学式: C₁₅H₁₅N
• 分子量: 209.291
• InChiKey: ZTMLMQJTUIPDJI-UHFFFAOYSA-N

物化性质

• 沸点：
  330.6±11.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-cyclopropyldiphenylamine 、 (η(5)-C5Me5)(PMe3)Ir(Me)(OTf) 以 二氯甲烷 为溶剂， 生成 [(pentamethylcyclopentadienyl)(PMe3)Ir(η3-C3H4CH3)][OTf]
  参考文献：
  名称：

  在阳离子铱配合物与杂原子取代的环丙烷反应中观察到意外的 C-C 键断裂和 C-C 键形成

  摘要：

  铱配合物 Cp*(PMe3)Ir(CH3)OTf (1) 和烷基氨基环丙烷通过众所周知的初始 C-H 键活化和随后的 C-C 键断裂步骤反应，生成各种 π-烯丙基配合物 [Cp *(PMe3)Ir(η3-C3H4NR1R2)][OTf]（R1 = R2 = Bn；R1 = Bn，R2 = Ph）和甲烷。然而，二苯基氨基、烷氧基或甲硅烷氧基环丙烷在用配合物 1 处理时，会产生新的 π-烯丙基配合物 [Cp*(PMe3)Ir(η3-C3H4CH3)][OTf] (8) 和相应的胺或醇。最初与铱结合的甲基不再作为甲烷被挤出，而是被结合到烯丙基部分以产生新的碳-碳键。详细的机理研究提供了支持初始 C-C 键激活机制的证据，而不是用其他已知底物观察到的初始 C-H 键激活。

  DOI：

  10.1021/ja068312a
• 作为产物：
  描述：

  1-chlorocyclopropyl phenyl sulfoxide 、 lithium diphenylamide 在 异丙基氯化镁 、 甲醇 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 N-cyclopropyldiphenylamine
  参考文献：
  名称：

  Reaction of magnesium cyclopropylidene with N-lithio arylamines: a method for generation of α-amino-substituted cyclopropylmagnesiums and a study for their reactivity with electrophiles

  摘要：

  Magnesium cyclopropylidene was generated from 1-chlorocyclopropyl phenyl sulfoxide with i-PrMgCl in THF at -78 degrees C in high yield by a sulfoxide-magnesium exchange reaction. The generated magnesium cyclopropylidene was found to be reactive with N-lithio arylamines to give alpha-ammo-substituted cyclopropylmagnesiums. The reaction of the a-amino-substituted cyclopropylmagnesiums with several electrophiles was examined and a new method for a synthesis of cyclopropane amino acid derivatives was realized. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.080

文献信息

• Transition-Metal-Free N-Arylation of Amines by Triarylsulfonium Triflates
  作者：Ze-Yu Tian、Xiao-Xia Ming、Han-Bing Teng、Yu-Tian Hu、Cheng-Pan Zhang

  DOI：10.1002/chem.201802269

  日期：2018.9.18

  primary amines under the standard conditions, the bis(N‐phenyl) products were predominantly formed. This method was also applicable to the synthesis of bioactive N‐phenyl amino acid derivatives. The control experiments, the deuterium labelling study, and the presence of regioisomers of N‐arylated products when using 4‐substituted triarylsulfonium triflates suggested that the reaction might proceed through

  本文介绍了一种简单有效的三芳基ulf三氟甲磺酸酯对各种胺进行无过渡金属N-芳基化的方法。在t BuOK或KOH存在下，脂族和芳族胺均在80°C下平稳转化，从而以高至高收率获得了相应的单N芳基化产物。反应物的摩尔比和碱的选择对反应有很大的影响。当在标准条件下将大量过量的[Ph 3 S] [OTf]和t BuOK用于伯胺时，主要形成了双（N-苯基）产物。该方法也适用于生物活性氮的合成-苯基氨基酸衍生物。对照实验，氘标记研究以及使用4-取代的三芳基ulf三氟甲磺酸酯时N芳基化产物的区域异构体的存在表明，该反应可能会通过芳烃中间体进行。本方案证明，三芳基ulf盐在C Ar -N键的构建中是通用的芳基化试剂。
• US3954778A
  申请人：——

  公开号：US3954778A

  公开（公告）日：1976-05-04
• Unexpected C−C Bond Cleavage and C−C Bond Formation Observed in the Reaction of a Cationic Iridium Complex with Heteroatom-Substituted Cyclopropanes
  作者：Mitchell R. Anstey、Cathleen M. Yung、Juana Du、Robert G. Bergman

  DOI：10.1021/ja068312a

  日期：2007.1.1

  [Cp*(PMe3)Ir(η3-C3H4CH3)][OTf] (8) and the corresponding amine or alcohol. The methyl group initially bound to iridium is no longer extruded as methane, but instead is incorporated into the allyl moiety to give a new carbon−carbon bond. A detailed mechanistic study provides evidence in support of an initial C−C bond activation mechanism as opposed to the initial C−H bond activation observed with other known

  铱配合物 Cp*(PMe3)Ir(CH3)OTf (1) 和烷基氨基环丙烷通过众所周知的初始 C-H 键活化和随后的 C-C 键断裂步骤反应，生成各种 π-烯丙基配合物 [Cp *(PMe3)Ir(η3-C3H4NR1R2)][OTf]（R1 = R2 = Bn；R1 = Bn，R2 = Ph）和甲烷。然而，二苯基氨基、烷氧基或甲硅烷氧基环丙烷在用配合物 1 处理时，会产生新的 π-烯丙基配合物 [Cp*(PMe3)Ir(η3-C3H4CH3)][OTf] (8) 和相应的胺或醇。最初与铱结合的甲基不再作为甲烷被挤出，而是被结合到烯丙基部分以产生新的碳-碳键。详细的机理研究提供了支持初始 C-C 键激活机制的证据，而不是用其他已知底物观察到的初始 C-H 键激活。
• Reaction of magnesium cyclopropylidene with N-lithio arylamines: a method for generation of α-amino-substituted cyclopropylmagnesiums and a study for their reactivity with electrophiles
  作者：Tsuyoshi Satoh、Mariko Miura、Ken Sakai、Yoshimi Yokoyama

  DOI：10.1016/j.tet.2006.01.080

  日期：2006.4

  Magnesium cyclopropylidene was generated from 1-chlorocyclopropyl phenyl sulfoxide with i-PrMgCl in THF at -78 degrees C in high yield by a sulfoxide-magnesium exchange reaction. The generated magnesium cyclopropylidene was found to be reactive with N-lithio arylamines to give alpha-ammo-substituted cyclopropylmagnesiums. The reaction of the a-amino-substituted cyclopropylmagnesiums with several electrophiles was examined and a new method for a synthesis of cyclopropane amino acid derivatives was realized. (c) 2006 Elsevier Ltd. All rights reserved.