N,N-二甲基-10-十一碳烯硫代酰胺 | 73160-88-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代酰胺
• 中文名称: N,N-二甲基-10-十一碳烯硫代酰胺
• 英文名称: undec-10-enethioic acid dimethylamide
• 英文别名: N,N-dimethylundec-10-enethioamide
• CAS: 73160-88-0
• 化学式: C₁₃H₂₅NS
• 分子量: 227.414
• InChiKey: CQNKMGYDXMXJBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-二甲基-10-十一碳烯硫代酰胺 、 乙酸烯丙酯 在 bis(η3-allyl-μ-chloropalladium(II)) 、 1,4-双(二苯基膦)丁烷 、 sodium t-butanolate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以76%的产率得到N,N-dimethyl-2-prop-2-enylundec-10-enethioamide
  参考文献：
  名称：

  Pd-catalyzed allylic alkylation of thioamides

  摘要：

  This work describes the first Pd-catalyzed allylic alkylation of thioamides. Various thioamides were efficiently alpha-allylated in high yields and with excellent selectivity for monoallylation under mild reaction conditions. The process not only provides a facile method for the synthesis of functionalized thioamides, but also presents a useful transformation for synthetically important thioamides. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.081

文献信息

• SYNTHESIS OF DIHYDRO-1,3-OXAZINES FROM THIOAMIDES
  作者：Toshiro Harada、Yoshinao Tamaru、Zen-ichi Yoshida

  DOI：10.1246/cl.1979.1353

  日期：1979.11.5

  A new method converting thioamides to the synthetically useful precursor, 2-substituted dihydro-1,3-oxazine, is described, in which the corresponding S-methyl thiouronium salts are refluxed with 4-amino-4-methyl-2-pentanol in tBuOH or CH2Cl2 to give the products in high yields.

  描述了一种将硫代酰胺转化为合成有用的前体 2-取代二氢-1,3-恶嗪的新方法，其中相应的 S-甲基硫脲盐与 4-氨基-4-甲基-2-戊醇在 tBuOH 中回流或 CH2Cl2 以高产率得到产物。
• Pd-catalyzed asymmetric α-allylic alkylation of thioamides
  作者：Bin Rong、Qin Yang、Yong Liu、Hong Xu、Yifan Hu、Xuejing Cheng、Baoguo Zhao

  DOI：10.1016/j.tetlet.2014.12.031

  日期：2015.1

  This Letter describes the first catalytic asymmetric alpha-allylic alkylation of thioamides. By using 5 mol % Pd-(R)-DM-BINAP complex as the chiral catalyst, various thioamides were efficiently alpha-allylic alkylated with 1,3-diarylallyl carbonates under mild conditions, affording a variety of alpha-substituted thioamides in good yields with high enantioselectivity and moderate diastereoselectivity. This work represents a useful and direct route to prepare chiral functionalized thioamides. (C) 2014 Elsevier Ltd. All rights reserved.
• Pd-catalyzed α-arylation of thioamides
  作者：Hailei Yu、Xuliang Liu、Lei Ding、Qin Yang、Bin Rong、Ang Gao、Baoguo Zhao、Haifeng Yang

  DOI：10.1016/j.tetlet.2013.03.114

  日期：2013.6

  Thioamides are unique and versatile synthetic building blocks with S, N, and alpha-C three adjacent nucleophile centers, however, they are rarely used as carbon nucleophiles for transition-metal-catalyzed C-C coupling reactions. This Letter describes the first Pd-catalyzed alpha-arylation of thioamides and demonstrated the feasibility of the application of thioamides in coupling chemistry. By the coupling process, a variety of alpha-arylated thioamides were prepared in moderate to good yields under mild reaction conditions, which provides an alternative way to access functionalized thioamides as well as a new synthetic transformation for thioamides. High chemoselectivity for thioamide over amide was observed in the reaction. (C) 2013 Elsevier Ltd. All rights reserved.
• HARADA T.; TAMARU Y.; YOSHIDA Z., TETRAHEDRON LETT., 1979, NO 37, 3525-3528
  作者：HARADA T.、 TAMARU Y.、 YOSHIDA Z.

  DOI：——

  日期：——
• HARADA TOSHIRO; TAMARU YOSHINAO; YOSHIDA ZEN-ICHI, CHEM. LETT., 1979, NO 11, 1353-1356
  作者：HARADA TOSHIRO、 TAMARU YOSHINAO、 YOSHIDA ZEN-ICHI

  DOI：——

  日期：——