1,1-Dimethylethyl N-[(3,5-dimethylphenyl)methyl]-N-[[4-(hydroxymethyl)phenyl]methyl]carbamate | 797789-08-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,1-Dimethylethyl N-[(3,5-dimethylphenyl)methyl]-N-[[4-(hydroxymethyl)phenyl]methyl]carbamate
• 英文别名: tert-butyl N-[(3,5-dimethylphenyl)methyl]-N-[[4-(hydroxymethyl)phenyl]methyl]carbamate
• CAS: 797789-08-3
• 化学式: C₂₂H₂₉NO₃
• 分子量: 355.477
• InChiKey: XFHWMDYKIYDVQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,1-Dimethylethyl N-[(3,5-dimethylphenyl)methyl]-N-[[4-(hydroxymethyl)phenyl]methyl]carbamate 在 三丁基膦 、 三氟乙酸 、 N,N'-二异丙基碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  Thermoresponsive Shuttling of Rotaxane Containing Trichloroacetate Ion

  摘要：

  A thermoresponsive rotaxane shuttling system was developed with a trichloroacetate counteranion of an ammonium/crown ether-type rotaxane. Chemoselective thermal decomposition of the ammonium trichloroacetate moiety on the rotaxane yielded the corresponding nonionic rotaxane accompanied by a positional change of the crown ether on the axle. The rotaxane skeleton facilitated effective dissociation of the acid, markedly lowering the thermal decomposition temperature.

  DOI：

  10.1021/ol301771w
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 Benzenemethanol, 4-[[[(3,5-dimethylphenyl)methyl]amino]methyl]- 在 4-二甲氨基吡啶 作用下， 以 氯仿 为溶剂， 以76%的产率得到1,1-Dimethylethyl N-[(3,5-dimethylphenyl)methyl]-N-[[4-(hydroxymethyl)phenyl]methyl]carbamate
  参考文献：
  名称：

  通过Diels-Alder反应对拟轮烷进行封端，以构建C60端接的[2]轮烷。

  摘要：

  [反应：见正文]诸如C（60）之类的各种亲二烯体与具有硫氰酸根部分的假轮烷的Diels-Alder反应以中等收率提供了相应的[2]轮烷。在车轮部件上引入卟啉部分极大地提高了与C（60）的封端反应的效率。

  DOI：

  10.1021/ol048433k

文献信息

• A Rational Design for the Directed Helicity Change of Polyacetylene Using Dynamic Rotaxane Mobility by Means of Through-Space Chirality Transfer
  作者：Fumitaka Ishiwari、Kei-ichiro Fukasawa、Takashi Sato、Kazuko Nakazono、Yasuhito Koyama、Toshikazu Takata

  DOI：10.1002/chem.201101727

  日期：2011.10.17

  main chain for the formation of a one‐handed helix. Through‐space chirality induction in the present systems proved to be as powerful as through‐bond chirality induction for formation of a one‐handed helix, as demonstrated in an experiment using non‐rotaxane‐based polyacetylene that had an optically active binaphthyl group. The present protocol for controlling the helical structure of polyacetylene therefore

  通过与置于侧链上的轮烷骨架杂交，实现了对聚乙炔动态螺旋的直接螺旋控制。通过由光学活性冠醚和仲铵盐与乙炔基苯甲酸组成的假轮烷的酯封端，以高收率合成了轮烷拴系的苯乙炔单体。单体与[RhCl（nbd）} 2 ]（nbd =降冰片二烯）聚合，以高收率得到相应的聚乙炔。具有远离主链的光学活性轮组分的聚合物没有棉花效应，因此表明外消旋螺旋的形成。我们的建议是仲胺的N-酰基中和通过观察主链吸收区周围的棉花效应，当车轮组分接近主链时，侧链轮烷部分的铵部分可实现单手螺旋的不对称诱导。尽管侧链轮烷部分具有铵结构，但带有侧链轮烷的聚乙炔具有较短的车轴成分，但仍显示出棉花效应，这表明轮与主链之间的亲近对于形成单链轮非常重要。螺旋。如在使用具有旋光性双萘基的非基于轮烷的聚乙炔的实验中所证明的，在本系统中，通过空间手性诱导与通过手性手性诱导形成单螺旋结构一样强大。
• End-Capping of a Pseudorotaxane via Diels−Alder Reaction for the Construction of C₆₀-Terminated [2]Rotaxanes
  作者：Hisahiro Sasabe、Nobuhiro Kihara、Yoshio Furusho、Kazuhiko Mizuno、Akiya Ogawa、Toshikazu Takata

  DOI：10.1021/ol048433k

  日期：2004.10.1

  [reaction: see text] The Diels-Alder reaction of various dienophiles such as C(60) with a pseudorotaxane having a sultine moiety afforded corresponding [2]rotaxanes in moderate yields. The introduction of a porphyrin moiety on the wheel component considerably enhanced the efficiency of the end-capping reaction with C(60).

  [反应：见正文]诸如C（60）之类的各种亲二烯体与具有硫氰酸根部分的假轮烷的Diels-Alder反应以中等收率提供了相应的[2]轮烷。在车轮部件上引入卟啉部分极大地提高了与C（60）的封端反应的效率。
• Solid-state Rotaxane Switch: Synthesis of Thermoresponsive Rotaxane Shuttle Utilizing a Thermally Decomposable Acid
  作者：Nan Zhu、Kazuko Nakazono、Toshikazu Takata

  DOI：10.1246/cl.151190

  日期：2016.4.5

  A thermoresponsive crown ether/amine-type rotaxane switch worked under solvent-free condition was developed. The wheel component moved to switch the local position on the axle by the solid-state ac...

  开发了一种在无溶剂条件下工作的热敏冠醚/胺型轮烷开关。车轮组件移动以切换轴上的局部位置，通过固态交流...
• End-Cap Exchange of Rotaxane by the Tsuji−Trost Allylation Reaction
  作者：Nobuhiro Kihara、Seiko Motoda、Tsutomu Yokozawa、Toshikazu Takata

  DOI：10.1021/ol047639i

  日期：2005.3.1

  Rotaxanes possessing a cinnamyl ester group at the axle terminal were prepared. The terminal end-cap was modified with a bulky malonate ester in excellent yield by the Tsuji-Trost allylation reaction, which was carried out in the presence of a palladium catalyst.
• Thermoresponsive Shuttling of Rotaxane Containing Trichloroacetate Ion
  作者：Yoko Abe、Hisashi Okamura、Kazuko Nakazono、Yasuhito Koyama、Satoshi Uchida、Toshikazu Takata

  DOI：10.1021/ol301771w

  日期：2012.8.17

  A thermoresponsive rotaxane shuttling system was developed with a trichloroacetate counteranion of an ammonium/crown ether-type rotaxane. Chemoselective thermal decomposition of the ammonium trichloroacetate moiety on the rotaxane yielded the corresponding nonionic rotaxane accompanied by a positional change of the crown ether on the axle. The rotaxane skeleton facilitated effective dissociation of the acid, markedly lowering the thermal decomposition temperature.