trans-crotonohydroxamic acid | 115615-46-8

• 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: trans-crotonohydroxamic acid
• 英文别名: trans-Crotonohydroxamsaeure；(E)-N-hydroxybut-2-enamide
• CAS: 115615-46-8
• 化学式: C₄H₇NO₂
• 分子量: 101.105
• InChiKey: BZDKOUKSFMIFNT-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-crotonohydroxamic acid 在 magnesium hydroxide 、 magnesium carbonate 作用下， 以 水 为溶剂， 反应 1.0h， 以45%的产率得到magnesium trans-crotonohydroxamate
  参考文献：
  名称：

  Crystal and Molecular Structure of Crotonohydroxamic Acid, and a Preliminary Investigation of the Solid-State Reactivity of the Acid and Its Salts

  摘要：

  The crystal structure of crotonohydroxamic acid, CH3CH=CHC(O)NHOH 5 contains centrosymmetrically-related pairs of acid molecules, with a short contact of 3.36 angstrom between the alpha-carbon atoms. The observed arrangement provides excellent alignment for a solid-state ene reaction, but, apparently, the threshold temperature for such a process cannot be realized. The hydrogen bonding patterns observed include C(5) chains and both R-2(4) (10) and R-4(4)(18) ring systems. Facile preparation of metal salts of the acid is reported, as well as discussion of the effect of heating and Co-60 gamma-irradiation of the materials.

  DOI：

  10.1080/15421400590958269
• 作为产物：
  描述：

  2-丁烯酰氯 在 盐酸羟胺 、 sodium carbonate 作用下， 以 水 、 乙酸乙酯 为溶剂， 生成 trans-crotonohydroxamic acid
  参考文献：
  名称：

  修饰的环戊二烯基RhIII配合物催化形式的Lossen重排/ [3 + 2]环空级联反应

  摘要：

  现已确定，具有两个苯基和一个侧基酰胺部分的环戊二烯基Rh III配合物催化N-新戊酰基苯甲酰胺和丙烯酰胺与炔烃的正式Lossen重排/ [3 + 2]环合级联反应，从而生成取代的吲哚和吡咯。机理研究表明，这种级联反应不是通过洛森重排形成苯胺或酰胺，而是通过CH键断裂，炔烃插入和形式上的洛森重排进行的。

  DOI：

  10.1002/chem.201801125

文献信息

• Ultraviolet Absorption Spectra of Some Hydroxamic Acids and Hydroxamic Acid Derivatives
  作者：ROBERT E. PLAPINGER

  DOI：10.1021/jo01088a017

  日期：1959.6
• KASAHARA A.; IZUMI T., CHEM. AND IND., 1979, NO 9, 318
  作者：KASAHARA A.、 IZUMI T.

  DOI：——

  日期：——
• Formal Lossen Rearrangement/[3+2] Annulation Cascade Catalyzed by a Modified Cyclopentadienyl Rh ^III Complex
  作者：Takayuki Yamada、Yu Shibata、Susumu Kawauchi、Soichi Yoshizaki、Ken Tanaka

  DOI：10.1002/chem.201801125

  日期：2018.4.17

  established that a cyclopentadienyl RhIII complex with two phenyl groups and a pendant amide moiety catalyzes the formal Lossen rearrangement/[3+2] annulation cascade of N‐pivaloyl benzamides and acrylamides with alkynes leading to substituted indoles and pyrroles. Mechanistic studies revealed that this cascade reaction proceeds via not the Lossen rearrangement to form anilides or enamides but C−H bond cleavage

  现已确定，具有两个苯基和一个侧基酰胺部分的环戊二烯基Rh III配合物催化N-新戊酰基苯甲酰胺和丙烯酰胺与炔烃的正式Lossen重排/ [3 + 2]环合级联反应，从而生成取代的吲哚和吡咯。机理研究表明，这种级联反应不是通过洛森重排形成苯胺或酰胺，而是通过CH键断裂，炔烃插入和形式上的洛森重排进行的。
• Crystal and Molecular Structure of Crotonohydroxamic Acid, and a Preliminary Investigation of the Solid-State Reactivity of the Acid and Its Salts
  作者：Magali B. Hickey、Bruce M. Foxman

  DOI：10.1080/15421400590958269

  日期：2005.7.1

  The crystal structure of crotonohydroxamic acid, CH3CH=CHC(O)NHOH 5 contains centrosymmetrically-related pairs of acid molecules, with a short contact of 3.36 angstrom between the alpha-carbon atoms. The observed arrangement provides excellent alignment for a solid-state ene reaction, but, apparently, the threshold temperature for such a process cannot be realized. The hydrogen bonding patterns observed include C(5) chains and both R-2(4) (10) and R-4(4)(18) ring systems. Facile preparation of metal salts of the acid is reported, as well as discussion of the effect of heating and Co-60 gamma-irradiation of the materials.