N,N-diethylundec-10-ynamide | 600710-41-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N,N-diethylundec-10-ynamide
• 英文别名: Undec-10-insaeure-diaethylamid；N,N-Diaethyl-undec-10-inamid
• CAS: 600710-41-6
• 化学式: C₁₅H₂₇NO
• 分子量: 237.385
• InChiKey: UCRCIBLZLIFZMT-UHFFFAOYSA-N

物化性质

• 沸点：
  343.7±25.0 °C(Predicted)
• 密度：
  0.898±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  17.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N,N-diethylundec-10-ynamide 在 三乙基硼 、 dichlorogallane 、 盐酸 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 以89%的产率得到N,N-diethylundec-10-enamide
  参考文献：
  名称：

  Triethylborane-Mediated Hydrogallation and Hydroindation:  Novel Access to Organogalliums and Organoindiums

  摘要：

  Hydrogallation of carbon-carbon multiple bonds proceeds in the presence of triethylborane as a radical initiator. Several functionalities do not interfere with this reaction. Resulting alkenyl- and alkylgallium species can be trapped by several electrophiles. Highly regioselective radical addition of an indium hydride reagent to alkynes is also achieved. Various functionalities are tolerant under the reaction conditions. The reaction proceeds with complete anti stereoselectivity. Alkenylindiums obtained via hydroindation can be employed for the following cross-coupling reaction with aryl halides in one pot.

  DOI：

  10.1021/jo0344790
• 作为产物：
  描述：

  undec-10-ynoyl chloride 、 二乙胺 在 苯 作用下， 生成 N,N-diethylundec-10-ynamide
  参考文献：
  名称：

  Antifungal Agents¹

  摘要：

  DOI：

  10.1021/ja01614a013

文献信息

• 一种含碳碳三键和/或碳氮三键的不饱和有机 化合物的还原氘化方法
  申请人：中国农业大学

  公开号：CN110294660B

  公开（公告）日：2021-09-24

  本发明的目的在于提供一种含碳碳三键和/或碳氮三键的不饱和有机化合物的还原氘化方法，该方法将碱金属媒介的单电子转移反应应用于碳碳三键或碳氮三键的还原中，能够在碱金属试剂、氘供体试剂、有机溶剂存在的条件下将炔烃类和腈类化合物分别转化为氘代烯烃(或烷烃)类和α,α‑二氘代胺类化合物。有机化合物中的卤素取代基在本反应条件下也会被还原生成相应的氘代化合物。本发明所述炔烃、腈、有机卤化物的新型还原方法产率和氘代率高、操作安全简单、原料易得，反应时间短，制备过程中没有使用过渡金属催化剂、昂贵且易燃的金属氘化物及可燃气体氘气等，且不产生有害副产物。
• Transition-Metal-Free, Selective Reductive Deuteration of Terminal Alkynes with Sodium Dispersions and EtOD-<i>d</i>₁
  作者：Minhui Han、Yuxuan Ding、Yuhao Yan、Hengzhao Li、Shihui Luo、Adila Adijiang、Yun Ling、Jie An

  DOI：10.1021/acs.orglett.8b01036

  日期：2018.5.18

  A transition-metal-free single electron transfer reaction has been developed for the synthesis of [D3]-alkenes from terminal alkynes using sodium dispersions as the electron donor and EtOD-d1 as the deuterium source. Both reagents are cost-effective and bench-stable. This practical method exhibits remarkable terminal alkyne selectivity and exclusive alkene selectivity. Excellent deuterium incorporations

  已经开发了无过渡金属的单电子转移反应，用于使用钠分散体作为电子供体，并使用EtOD- d 1作为氘源，从末端炔烃中合成[D 3 ]-烯烃。两种试剂均具有成本效益且稳定。这种实用的方法表现出显着的末端炔烃选择性和专有的烯烃选择性。在没有烯烃异构化的情况下，在各种末端炔烃中都实现了出色的氘掺入和收率。值得注意的是，该反应高度依赖溶剂。ñ正己烷提供了独特的增强，这个还原过程氘。
• Mild and Selective Hydrozirconation of Amides to Aldehydes Using Cp₂Zr(H)Cl:  Scope and Mechanistic Insight
  作者：Jared T. Spletstoser、Jonathan M. White、Ashok Rao Tunoori、Gunda I. Georg

  DOI：10.1021/ja066362+

  日期：2007.3.1

  An investigation of the use of Cp2Zr(H)Cl (Schwartz's reagent) to reduce a variety of amides to the corresponding aldehydes under very mild reaction conditions and in high yields is reported. A range of tertiary amides, including Weinreb's amides, can be converted directly to the corresponding aldehydes with remarkable chemoselectivity. Primary and secondary amides proved to be viable substrates for reduction as well, although the yields were somewhat diminished as compared to the corresponding tertiary amides. Results from NMR experiments suggested the presence of a stable, 18-electron zirconacycle intermediate that presumably affords the aldehyde upon water or silica gel workup. A series of competition experiments revealed a preference of the reagent for substrates in which the lone pair of the nitrogen is electron releasing and thus more delocalized across the amide bond by resonance. This trend accounts for the observed excellent selectivity for tertiary amides versus esters. Experiments regarding the solvent dependence of the reaction suggested a kinetic profile similar to that postulated for the hydrozirconation of alkenes and alkynes. Addition of p-anisidine to the reaction intermediate resulted in the formation of the corresponding imine mimicking the addition of water that forms the aldehyde.