(R)-4-vinyloxazolidin-2-one | 154334-64-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (R)-4-vinyloxazolidin-2-one
• 英文别名: (4R)-4-ethenyl-1,3-oxazolidin-2-one
• CAS: 154334-64-2
• 化学式: C₅H₇NO₂
• 分子量: 113.116
• InChiKey: WRQDRNWXVRNPFT-SCSAIBSYSA-N

物化性质

• 沸点：
  301.0±22.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-4-vinyloxazolidin-2-one 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 氢气 、 sodium hydride 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 、 mineral oil 为溶剂， 反应 5.5h， 生成 (7R,7aR,Z)-6-ethylidene-7-methyltetrahydropyrrolo[1,2-c]oxazol-3(1H)-one
  参考文献：
  名称：

  Rhodium-catalyzed reductive cyclization of 1,6-enynes and stereoselective synthesis of the putative structure of lucentamycin A and its stereoisomers

  摘要：

  A Rh-catalyzed diastereoselective reductive cyclization, mediated by hydrogen, of optically active 1,6-enynes using chiral BINAP was successfully applied to the total synthesis of four stereoisomers of the proposed structure of lucentamycin A. In order to synthesize two of these four stereoisomers, we successfully constructed chiral proline derivatives bearing cis-carbon substituents at C2 and C3 positions based on Krische's methodology, which has very rarely been reported. Anti-proliferative activities on HCT-116 cell line and NMR data of these four stereoisomers were compared with those of naturally occurring lucentamycine A. The results show that the proposed structure of lucentamycin A needs revision. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.075
• 作为产物：
  描述：

  (R)-2-氨基-3-丁烯-1-醇盐酸盐 在 三光气 、 碳酸氢钠 作用下， 以 水 、 甲苯 为溶剂， 反应 14.0h， 以82%的产率得到(R)-4-vinyloxazolidin-2-one
  参考文献：
  名称：

  通过铑（III）催化的氧化sp2C-H键烯烃简明合成真菌代谢物（+）- Fusarochromanone

  摘要：

  真菌代谢物 (+)-fusarochromanone (FC-101) 的简明合成是通过 N-乙酰氨基色满酮与手性功能化的富电子烯烃的氧化 sp2 C-H 键烯化实现的，由缺电子催化(η5-环戊二烯基)铑(III)配合物，[CpERhCl2]2，在环境条件下作为关键步骤。该协议适用于各种乙酰苯胺和功能化的富电子烯烃，用于合成 fusarochromanone 类似物。

  DOI：

  10.1246/cl.160530

文献信息

• TETRACYCLIC CDK9 KINASE INHIBITORS
  申请人：AbbVie Inc.

  公开号：US20150218165A1

  公开（公告）日：2015-08-06

  Disclosed are compounds of Formula (Ia), and pharmaceutically acceptable salts thereof, wherein X, Y, R 1 , R 2 , R 3A , R 3B , and R 4 are as described herein. The compounds may be used as agents in the treatment of diseases, including cancer. Also disclosed are pharmaceutical compositions comprising one or more compounds of Formula (Ia).

  公开了公式(Ia)的化合物，以及其中X、Y、R1、R2、R3A、R3B和R4如本文所述的药用可接受盐。这些化合物可用作治疗疾病(包括癌症)的药物。还公开了包含一个或多个公式(Ia)化合物的药物组合物。
• Catalytic asymmetric synthesis of stereoisomers of 1-C-n-butyl-LABs for the SAR study of α-glucosidase inhibition
  作者：Yoshihiro Natori、Toshihiro Sakuma、Haruka Watanabe、Hideaki Wakamatsu、Atsushi Kato、Isao Adachi、Hiroki Takahata、Yuichi Yoshimura

  DOI：10.1016/j.tet.2019.04.003

  日期：2019.5

  a diol unit at C2 and C3 to give the desired stereoisomers of L-iminofuranose derivatives. We achieved the preparation of all stereoisomers of 1-C-n-butyl-L-iminofuranose derivatives, with the exception of β-lyxo type iminofuranose. It is noteworthy that a synthetic route for many stereoisomers of iminofuranose derivatives was developed. Unfortunately, none of the L-iminofuranoses obtained showed inhibitory

  我们实现了七个立体异构体的1-合成的C n -使用催化不对称烷基化和Negishi偶联作为关键反应丁基-L- iminofuranose衍生物。基于这些关键反应的合成策略非常有用，因为可以通过切换用于AAA反应的配体的手性来获得α-和β-亚氨基呋喃糖。对α-和β-异构体的常用中间体进行进一步处理，以在C2和C3处安装一个二醇单元，以得到所需的L-亚氨基呋喃糖衍生物的立体异构体。我们实现了1- Cn-的所有立体异构体的制备丁基-L-亚氨基呋喃糖衍生物，但β-lyxo型亚氨基呋喃糖除外。值得注意的是，开发了亚氨基呋喃糖衍生物的许多立体异构体的合成途径。不幸的是，所获得的L-亚氨基呋喃糖酶均未显示出对所检查的α-糖苷酶的抑制活性，例如，麦芽糖酶，蔗糖酶和异麦芽糖酶。
• Progress toward the Total Synthesis of Lucentamycin A: Total Synthesis and Biological Evaluation of 8-<i>epi</i>-Lucentamycin A
  作者：R. Nathan Daniels、Bruce J. Melancon、Emily A. Wang、Brenda C. Crews、Lawrence J. Marnett、Gary A. Sulikowski、Craig W. Lindsley

  DOI：10.1021/jo902115s

  日期：2009.11.20

  Synthetic efforts toward the cytotoxic peptides lucentamycins A−D are described that resulted in the total synthesis and biological evaluation of 8-epi-lucentamycin A in 15 steps with 2.2% overall yield. The key epi-nonproteogenic 3-methyl-4-ethylideneproline was synthesized via a titanium-mediated cycloisomerization reaction.

  描述了对细胞毒性肽 lucentamycins A-D 的合成努力，导致 8- epi- lucentamycin A的全合成和生物学评估分15 个步骤，总产率为 2.2%。关键外延-nonproteogenic 3-甲基-4- ethylideneproline经由钛介导的环异构反应合成。
• An Improved Procedure for the Preparation of the Garner Aldehyde and Its Use for the Synthesis of<i>N</i>-Protected 1-Halo-2-(<i>R</i>)-amino-3-butenes
  作者：Alexander Mckillop、Richard J. K. Taylor、Robert J. Watson、Norman Lewis

  DOI：10.1055/s-1994-25398

  日期：——

  An improved procedure for the preparation of 1,1-dimethylethyl 2,2-dimethyl-4-(S)-formyloxazolidine-3-carboxylate (Garner aldehyde) is described which avoids the need for methyl iodide and benzene. Elaboration of this aldehyde into the novel chiral building blocks mentioned in the title is also described.

  本文介绍了制备 2,2-二甲基-4-(S)-甲酰恶唑烷-3-羧酸 1,1-二甲基乙酯（加纳醛）的改进程序，该程序避免了碘甲烷和苯的使用。此外，还介绍了将这种醛细化为标题中提到的新型手性构件的过程。
• A new synthetic method for an acromelic acid analog, a potent neuroexcitatory kainoid amino acid, via photoinduced benzyl radical cyclization
  作者：Satoshi Itadani、Shigeyuki Takai、Chieko Tanigawa、Kimiko Hashimoto、Haruhisa Shirahama

  DOI：10.1016/s0040-4039(02)01817-8

  日期：2002.10

  A new synthetic method for an acromelic acid analog, MFPA, was developed. The key step is the photoinduced benzyl radical cyclization with excellent stereoselectivity.

  开发了一种新的丙烯醛类似物MFPA的合成方法。关键步骤是光诱导的苄基自由基环化，具有出色的立体选择性。