N-hydroxyundecanamide | 15311-99-6

• 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: N-hydroxyundecanamide
• 英文别名: Undecanamide, N-hydroxy-
• CAS: 15311-99-6
• 化学式: C₁₁H₂₃NO₂
• 分子量: 201.309
• InChiKey: NRFHAFBKEFEPQH-UHFFFAOYSA-N

物化性质

• 密度：
  0.942±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  N-hydroxyundecanamide 在 C₃₇H₄₈ClIrN₂O₂S 、 四(3,5-二(三氟甲基)苯基)硼酸钠 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 (+)-5(R)-n-Heptyl-2-pyrrolidinone
  参考文献：
  名称：

  Strategic Approach to the Metamorphosis of γ-Lactones to NH γ-Lactams via Reductive Cleavage and C–H Amidation

  摘要：

  A new approach has elaborated on the conversion of γ-lactones to the corresponding NH γ-lactams that can serve as γ-lactone bioisosteres. This approach consists of reductive C-O cleavage and an Ir-catalyzed C-H amidation, offering a powerful synthetic tool for accessing a wide range of valuable NH γ-lactam building blocks starting from γ-lactones. The synthetic utility was further demonstrated by the late-stage transformation of complex bioactive molecules and the asymmetric transformation.

  DOI：

  10.1021/acs.orglett.9b02673
• 作为产物：
  描述：

  桃醛 在 hafnium tetrakis(trifluoromethanesulfonate) 、 草酰氯 、 palladium on activated carbon 、 盐酸羟胺 、 氢气 、 potassium carbonate 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 135.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 生成 N-hydroxyundecanamide
  参考文献：
  名称：

  Strategic Approach to the Metamorphosis of γ-Lactones to NH γ-Lactams via Reductive Cleavage and C–H Amidation

  摘要：

  A new approach has elaborated on the conversion of γ-lactones to the corresponding NH γ-lactams that can serve as γ-lactone bioisosteres. This approach consists of reductive C-O cleavage and an Ir-catalyzed C-H amidation, offering a powerful synthetic tool for accessing a wide range of valuable NH γ-lactam building blocks starting from γ-lactones. The synthetic utility was further demonstrated by the late-stage transformation of complex bioactive molecules and the asymmetric transformation.

  DOI：

  10.1021/acs.orglett.9b02673

文献信息

• Photoorganocatalytic One-Pot Synthesis of Hydroxamic Acids from Aldehydes
  作者：Giorgos N. Papadopoulos、Christoforos G. Kokotos

  DOI：10.1002/chem.201600333

  日期：2016.5.10

  An efficient one‐pot synthesis of hydroxamic acids from aldehydes and hydroxylamine is described. A fast, visible‐light‐mediated metal‐free hydroacylation of dialkyl azodicarboxylates was used to develop the subsequent addition of hydroxylamine hydrochloride. A range of aliphatic and aromatic aldehydes were employed in this reaction to give hydroxamic acids in high to excellent yields. Application

  描述了一种有效的一锅法从醛和羟胺合成异羟肟酸的方法。快速，可见光介导的偶氮二羧酸二烷基酯的无金属加氢酰化反应用于随后添加盐酸羟胺的过程。在该反应中使用了一系列脂族和芳族醛，以高产率或优异产率得到异羟肟酸。在抗癌药伏立诺他的合成中证明了当前方法的应用。
• Cross metathesis-mediated synthesis of hydroxamic acid derivatives
  作者：Shital Kumar Chattopadhyay、Subhankar Ghosh、Suman Sil

  DOI：10.3762/bjoc.14.285

  日期：——

  An alternative synthesis of α,ß-unsaturated hydroxamates via cross metathesis between a class-I olefin and N-benzyloxyacrylamide is reported. The reaction proceeds better in the presence of Grubbs' second generation catalyst within short time and in good yields (57-85%) with a range of substrates. Subsequent hydrogenation of each of the CM products delivers the title compounds in moderate to very good

  据报道，通过I类烯烃和N-苄氧基丙烯酰胺之间的交叉复分解，可以合成α，ß-不饱和异羟肟酸酯。在格拉布斯第二代催化剂的存在下，该反应在短时间内以多种底物在较高收率下（57-85％）更好地进行。随后，每种CM产品的氢化反应都会以中等至非常高的收率（70-89％）提供标题化合物。该协议的一个重要证明是生物活性环状肽Chap-31的异常氨基酸成分的制备。
• ANTIMICROBIAL COMPOSITION INCLUDING A DIHYDROXAMIC ACID AND METHODS OF INHIBITING MICROBIAL GROWTH UTILIZING THE SAME
  申请人：Kimberly-Clark Worldwide, Inc.

  公开号：US20200120929A1

  公开（公告）日：2020-04-23

  Antimicrobial compositions and methods for inhibiting microbial growth are disclosed. The antimicrobial compositions can include an antimicrobial agent that includes a dihydroxamic acid having a carbon chain length less than or equal to 7.
• [EN] ANTIMICROBIAL COMPOSITION INCLUDING A DIHYDROXAMIC ACID AND METHODS OF INHIBITING MICROBIAL GROWTH UTILIZING THE SAME<br/>[FR] COMPOSITION ANTIMICROBIENNE COMPRENANT UN ACIDE DIHYDROXAMIQUE ET MÉTHODES D'INHIBITION DE LA PROLIFÉRATION MICROBIENNE L'UTILISANT
  申请人：KIMBERLY CLARK CO

  公开号：WO2019005064A1

  公开（公告）日：2019-01-03

  Antimicrobial compositions and methods for inhibiting microbial growth are disclosed. The antimicrobial compositions can include an antimicrobial agent that includes a dihydroxamic acid having a carbon chain length less than or equal to 7.