3,3-dimethylbut-1-en-2-yl dimethylcarbamate | 1527478-08-5

• 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: 3,3-dimethylbut-1-en-2-yl dimethylcarbamate
• 英文别名: 3,3-dimethylbut-1-en-2-yl N,N-dimethylcarbamate
• CAS: 1527478-08-5
• 化学式: C₉H₁₇NO₂
• 分子量: 171.239
• InChiKey: BPBLNNAWZYYVPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  4-methyl-penta-2,3-dienoic acid ethyl ester 、 3,3-dimethylbut-1-en-2-yl dimethylcarbamate 在 四氢吡喃 、 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper diacetate 作用下， 反应 24.0h， 以57%的产率得到(2E,4Z)-ethyl 5-(dimethylcarbamoyloxy)-6,6-dimethyl-3-(prop-1-en-2-yl)hepta-2,4-dienoate
  参考文献：
  名称：

  Rh(III)-Catalyzed C–H Activation with Allenes To Synthesize Conjugated Olefins

  摘要：

  Rh-III-catalyzed C-H activation with allenes produces highly unsaturated conjugated olefins. The reaction is applicable to both olefin and arene C(sp(2))-H and is compatible with a variety of functional groups. The products can be further transformed into other important skeletons through Diels-Alder reaction and intramolecular transesterification.

  DOI：

  10.1021/ol403407q
• 作为产物：
  描述：

  频哪酮 、 二甲氨基甲酰氯 在 sodium hydride 、 二甲基亚砜 作用下， 反应 0.25h， 以33%的产率得到3,3-dimethylbut-1-en-2-yl dimethylcarbamate
  参考文献：
  名称：

  Rh(III)-Catalyzed C–H Activation with Allenes To Synthesize Conjugated Olefins

  摘要：

  Rh-III-catalyzed C-H activation with allenes produces highly unsaturated conjugated olefins. The reaction is applicable to both olefin and arene C(sp(2))-H and is compatible with a variety of functional groups. The products can be further transformed into other important skeletons through Diels-Alder reaction and intramolecular transesterification.

  DOI：

  10.1021/ol403407q

文献信息

• Rhodium‐Catalyzed Vinylic C–H Functionalization of Enol Carbamates with Maleimides
  作者：Satyasheel Sharma、Sang Hoon Han、Hyeim Jo、Sangil Han、Neeraj Kumar Mishra、Miji Choi、Taejoo Jeong、Jihye Park、In Su Kim

  DOI：10.1002/ejoc.201600558

  日期：2016.7

  The rhodium(III)-catalyzed direct C–H functionalization of enol carbamates with a range of maleimides is described. With the assistance of the carbamoyl directing group, this reaction provides biologically relevant succinimide compounds by proceeding through a C–Rh addition and subsequent protonation pathway.

  描述了铑 (III) 催化的烯醇氨基甲酸酯与一系列马来酰亚胺的直接 C-H 官能化。在氨基甲酰基导向基团的帮助下，该反应通过 C-Rh 加成和随后的质子化途径提供生物相关的琥珀酰亚胺化合物。
• Using Rh(III)-Catalyzed C–H Activation as a Tool for the Selective Functionalization of Ketone-Containing Molecules
  作者：Mélissa Boultadakis-Arapinis、Matthew N. Hopkinson、Frank Glorius

  DOI：10.1021/ol500258q

  日期：2014.3.21

  Due to the strong potential of C H activation in many areas of organic chemistry, the use of a pre-existing carbonyl group for the installation of a directing group to enable selective and predictable alpha-alkenylation with activated olefins as coupling partners is described. This Heck-type reaction would then lead either to beta,gamma-unsaturated ketones or to variously substituted 1,4-butadienes depending on the conditions used for the cleavage of the directing group.