(1R)-1-羟基-4-甲氧基-2-氧代环戊-3-烯-1-羧酸甲酯 | 76280-92-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (1R)-1-羟基-4-甲氧基-2-氧代环戊-3-烯-1-羧酸甲酯
• 英文名称: (S)-(-)-Kjellmanianone
• 英文别名: (S)-(+)-Kjellmanianone；methyl (1S)-1-hydroxy-4-methoxy-2-oxocyclopent-3-ene-1-carboxylate
• CAS: 76280-92-7
• 化学式: C₈H₁₀O₅
• 分子量: 186.164
• InChiKey: YGCFLXLGPRNGTJ-QMMMGPOBSA-N

物化性质

• 沸点：
  319.0±42.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  S-(2,6-dimethylphenyl) 4-methoxy-2-oxocyclopent-3-ene-1-carbothioate 在 manganese(IV) oxide 、 silver trifluoroacetate 、 copper(II) bis(trifluoromethanesulfonate) 、 (R,R)-2,2'-异亚丙基双(4-苯基-2-恶唑啉) 、 molybdenum hexacarbonyl 作用下， 以 四氢呋喃 、 氯仿 、 水 、 乙腈 为溶剂， 反应 56.0h， 生成 (1R)-1-羟基-4-甲氧基-2-氧代环戊-3-烯-1-羧酸甲酯
  参考文献：
  名称：

  Catalytic Enantioselective O-Nitrosocarbonyl Aldol Reaction of β-Dicarbonyl Compounds

  摘要：

  The first example of a Cu-catalyzed asymmetric O-nitrosocarbonyl aldol reaction is described. This novel protocol allows convenient access to highly enantioenriched alpha-hydroxy-beta-ketoesters including the antibacterial natural. product kjellmanianone (up to 99% ee). MnO2 was introduced. as a:mild efficient oxidant for the in situ generation of nitrosocarbonyl species from hydroxamic acid derivatives.

  DOI：

  10.1021/ja309311z

文献信息

• Diterpenoid Alkaloid Lappaconine Derivative Catalyzed Asymmetric α-Hydroxylation of β-Dicarbonyl Compounds with Hydrogen Peroxide
  作者：Zhi Li、Mingming Lian、Fan Yang、Qingwei Meng、Zhanxian Gao

  DOI：10.1002/ejoc.201402019

  日期：2014.6

  Scheme 1. Diterpenoid alkaloid lappaconine and preparation of lappaconine derivatives.[a] State Key Laboratory of Fine ChemicalsSchool of Pharmaceutical Science and TechnologyDalian University of TechnologyNo. 2 Linggong Road, Ganjingzi District, Dalian, LiaoningProvince 116012, P. R. ChinaE-mail: [e-mail]://ceb.dlut.edu.cn/index.html[b] Department of Pharmaceutics, Daqing CampusHarbin

  方案1.二萜生物碱拉帕康宁及其衍生物的制备[a]精细化工国家重点实验室大连理工大学药学院No. 辽宁省大连市甘井子区灵工路 2 号 116012 邮箱：[e-mail]://ceb.dlut.edu.cn/index.html[b] 大庆校区药学系哈尔滨医科大学 中国黑龙江省大庆市高新区信阳路 1 号 163319 本文的支持信息可在 WWW 上获得，网址为 http://dx.doi.org/10.1002/ejoc.201402019。
• Enantioselective synthesis of (+)-kjellmanianone
  作者：Bang-Chi Chen、Michael C. Weismiller、Franklin A. Davis、Diane Boschelli、James R. Empfield、Amos B. Smith

  DOI：10.1016/s0040-4020(01)80914-5

  日期：1991.1

  An asymmetric synthesis of the highly oxygenated cyclopentanoid antibiotic (+)-kjellmanianone (1) has been achieved. The key step entailed enantioselective hydroxylation of the prochiral sodium enolate of β-keto ester 2 with the new, enantiomerically pure N-sulfonyloxaziridine 7b, affording 1 in 68.5% ee (60% yield). Possible transition state structures for the asymmetric oxidation are evaluated.

  已经实现了高度氧化的环戊烷类抗生素（+）-kjellmanianone（1）的不对称合成。关键步骤是用新的对映体纯的N-磺酰基氧氮丙啶7b将β-酮酸酯2的前手性烯醇钠的对映体选择性羟基化，得到1的68.5％ee（收率60％）。对不对称氧化的可能过渡态结构进行了评估。
• Catalytic Enantioselective <i>O</i>-Nitrosocarbonyl Aldol Reaction of β-Dicarbonyl Compounds
  作者：Mahiuddin Baidya、Kimberly A. Griffin、Hisashi Yamamoto

  DOI：10.1021/ja309311z

  日期：2012.11.14

  The first example of a Cu-catalyzed asymmetric O-nitrosocarbonyl aldol reaction is described. This novel protocol allows convenient access to highly enantioenriched alpha-hydroxy-beta-ketoesters including the antibacterial natural. product kjellmanianone (up to 99% ee). MnO2 was introduced. as a:mild efficient oxidant for the in situ generation of nitrosocarbonyl species from hydroxamic acid derivatives.