2-(cyclopent-2-en-1-yl)-N-methoxy-N-methylacetamide | 877070-40-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(cyclopent-2-en-1-yl)-N-methoxy-N-methylacetamide
• 英文别名: 2-cyclopent-2-en-1-yl-N-methoxy-N-methylacetamide
• CAS: 877070-40-1
• 化学式: C₉H₁₅NO₂
• mdl: MFCD22414363
• 分子量: 169.224
• InChiKey: JNOJHPUQYYHRIT-UHFFFAOYSA-N

物化性质

• 沸点：
  220.7±23.0 °C(Predicted)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(cyclopent-2-en-1-yl)-N-methoxy-N-methylacetamide 在 sodium tetrahydroborate 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 生成 1-Cyclopent-2-en-1-yl-5-methylhex-5-en-3-yn-2-ol
  参考文献：
  名称：

  An expedient approach to allenes and polycyclic structures using propargyl radicals

  摘要：

  A general approach to the synthesis of allenes and polycyclic structures has been developed, based on the addition of a xanthate to an enyne followed by ring-closure of the allenyl radical on to an internal olefin. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.154
• 作为产物：
  描述：

  2-环戊烯基-1-乙酸 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 2-(cyclopent-2-en-1-yl)-N-methoxy-N-methylacetamide
  参考文献：
  名称：

  肟激进晋升双加氧，Oxyamination，和烯的Diamination：异恶唑啉和循环硝酮的合成

  摘要：

  出速度：分子内除了肟基团到CC键的通过使用DEAD和TEMPO，得到4,5- dihydroisoxazoles作为结果实现一个C  O键形成，5-外-trig环化。γ，δ不饱和酮肟也反应至C，得到环状硝酮 N键的形成。这些反应为未活化烯烃的邻位双官能化提供了一种无金属的方法。

  DOI：

  10.1002/anie.201203799

文献信息

• Oxime Radical Promoted Dioxygenation, Oxyamination, and Diamination of Alkenes: Synthesis of Isoxazolines and Cyclic Nitrones
  作者：Bing Han、Xiu-Long Yang、Ran Fang、Wei Yu、Chao Wang、Xiao-Yong Duan、Shuai Liu

  DOI：10.1002/anie.201203799

  日期：2012.8.27

  Up the tempo: The intramolecular addition of oxime radicals to CC bonds was achieved by using DEAD and TEMPO to give 4,5‐dihydroisoxazoles as a result of a CO bond‐forming, 5‐exo‐trig cyclization. γ,δ‐Unsaturated ketoximes also reacted to afford cyclic nitrones through CN bond formation. The reactions offer a metal‐free approach for the vicinal difunctionalization of unactivated alkenes.

  出速度：分子内除了肟基团到CC键的通过使用DEAD和TEMPO，得到4,5- dihydroisoxazoles作为结果实现一个C  O键形成，5-外-trig环化。γ，δ不饱和酮肟也反应至C，得到环状硝酮 N键的形成。这些反应为未活化烯烃的邻位双官能化提供了一种无金属的方法。
• Transition from π Radicals to σ Radicals: Substituent-Tuned Cyclization of Hydrazonyl Radicals
  作者：Xiao-Yong Duan、Neng-Neng Zhou、Ran Fang、Xiu-Long Yang、Wei Yu、Bing Han

  DOI：10.1002/anie.201309918

  日期：2014.3.17

  Hydrazonyl radicals are known for their π‐electronic structures; however, their σ‐electronic structures have not been reported as yet. Herein, we show that readily accessible β,γ‐ and γ,δ‐unsaturated N‐trichloroacetyl and N‐trifluoroacetyl hydrazones can be conveniently converted into hydrazonyl σ radicals, which subsequently undergo 5‐exo‐trig radical cyclization at the N1 or N2 atom to form pyrazolines

  羟基自由基以其π电子结构而著称；然而，它们的σ电子结构尚未被报道。在这里，我们表明容易获得的β，γ和γ，δ不饱和N-三氯乙酰基和N-三氟乙酰基可以方便地转化为肼基σ自由基，随后在N 1或N处进行5 exo- trig自由基环化。2个原子分别形成吡唑啉和甲亚胺亚胺。
• SYNTHESIS OF DELTA 12-PGJ3 AND RELATED COMPOUNDS
  申请人：WILLIAM MARSH RICE UNIVERSITY

  公开号：US20160318862A1

  公开（公告）日：2016-11-03

  In one aspect, the present invention provides novel derivatives of Δ 12 -PGJ 3 and modular synthetic pathways to obtaining Δ 12 -PGJ 3 and derivatives thereof. In some aspects, the present derivatives of Δ 12 -PGJ 3 are useful as chemotherapeutic agents. The present disclosure also describes compositions of these derivatives as well as methods of use of the derivatives thereof.
• An expedient approach to allenes and polycyclic structures using propargyl radicals
  作者：Celia Alameda-Angulo、Béatrice Quiclet-Sire、Samir Z. Zard

  DOI：10.1016/j.tetlet.2005.11.154

  日期：2006.2

  A general approach to the synthesis of allenes and polycyclic structures has been developed, based on the addition of a xanthate to an enyne followed by ring-closure of the allenyl radical on to an internal olefin. (c) 2005 Elsevier Ltd. All rights reserved.
• Iminoxyl Radical-Promoted Dichotomous Cyclizations: Efficient Oxyoximation and Aminooximation of Alkenes
  作者：Xie-Xue Peng、Yun-Jing Deng、Xiu-Long Yang、Lin Zhang、Wei Yu、Bing Han

  DOI：10.1021/ol502258n

  日期：2014.9.5

  A novel iminoxyl radical-involved metal-free approach to vicinal oxyoximation and aminooximation of unactivated alkenes is developed. This method utilizes the dichotomous reactivity of the iminoxyl radical to furnish a general difunctionalization on alkenes using simple tert-butyl nitrite (TBN) as the iminoxyl radical initiator as well the carbon radical trap. By using this protocol, oxime featured 4,5-dihydroisoxazoles and cyclic nitrones were facilely prepared from beta,gamma- and gamma,delta-unsaturated ketoximes, respectively.