(S)-4-hydroxy-2-methylcyclopent-2-en-1-one | 143562-63-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-4-hydroxy-2-methylcyclopent-2-en-1-one
• 英文别名: (4S)-4-hydroxy-2-methylcyclopent-2-en-1-one
• CAS: 143562-63-4
• 化学式: C₆H₈O₂
• 分子量: 112.128
• InChiKey: QSAULTQZSJKLPS-RXMQYKEDSA-N

物化性质

• 沸点：
  243.0±39.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-4-hydroxy-2-methylcyclopent-2-en-1-one 在 咪唑 、 过氧乙酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 正丁基锂 、 cerium(III) chloride 、 amberlyst-15 、 [(bicyclo[2.2.1]hepta-2,5-diene)(1,4-bis(diphenylphosphino)butane)rhodium(I)] tetrafluoroborate 、 Celite 、 四丁基氟化铵 、 水 、 氢气 、 sodium acetate 、 triphenylmethylium hexachloroantimonate(V) 、 mercuric triflate 、 二异丁基氢化铝 、 对甲苯磺酸 、 N,N-二甲基苯胺 、 三乙胺 、 N,N-二异丙基乙胺 、 pyridinium chlorochromate 、 silver(l) oxide 、 zinc dibromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 xylene 为溶剂， -78.0~50.0 ℃ 、6.89 MPa 条件下， 反应 179.58h， 生成 帚天人菊素C
  参考文献：
  名称：

  Tanis, Steven P.; Robinson, Edward D.; McMills, Mark C., Journal of the American Chemical Society, 1992, vol. 114, # 22, p. 8349 - 8362

  摘要：

  DOI：
• 作为产物：
  描述：

  4-methoxy-3-methyl-2-oxocyclopent-3-en-1-yl acetate 在 lithium aluminium tetrahydride 、 pig liver esterase 、 potassium phosphate buffer 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 16.0h， 生成 (S)-4-hydroxy-2-methylcyclopent-2-en-1-one
  参考文献：
  名称：

  A new and efficient chemoenzymatic route to both enantiomers of α′-acetoxy-α-methyl and γ-hydroxy-α-methyl cyclic enones

  摘要：

  A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting alpha'-acetoxy-alpha-methyl and gamma-hydroxy-alpha-methyl cyclic enones starting from alpha-methyl-beta-methoxy cyclic enones is reported. Manganese(Ill) acetate-mediated acetoxylation followed by the enzyme-mediated hydrolysis of alpha'-acetoxy enone provides acetoxy enones 1a and 2a and hydroxy enones 1b and 2b with high enantiomeric excesses in good yields. The reduction of the acetoxy and hydroxy enones furnished both enantiomers of gamma-hydroxy-alpha-methyl cyclic enones 3 and 4 in a high enantiomeric excess. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.12.006

文献信息

• A convenient preparation of (S)-(−)-4-hydroxy-2-methylcyclopent-2-en-1-one and its application as a chiral synthetic equivalent of 2-methylcyclopent-2-en-1-one in the terpenoid synthesis
  作者：Karol Michalak、Jerzy Wicha

  DOI：10.1016/j.tet.2014.06.006

  日期：2014.8

  from 1-(2-furyl)ethanol using modified Piancatelli rearrangement and enzymatic kinetic resolution of the racemate was developed. An application of O-protected derivatives of 4-hydroxy-2-methylcyclopent-2-en-1-one to terpenoid synthesis through tandem conjugate addition of allyl-metal reagents, enolate trapping, and consecutive Mukaiyama–Michael addition was studied. An optically active azulene derivative

  开发了一种通过修饰的Piancatelli重排和消旋体的酶促动力学拆分从1-（2-呋喃基）乙醇制备（S）-4-羟基-2-甲基环戊-2-烯-1-酮的方法。通过串联共轭添加烯丙基金属试剂，烯醇盐捕集和连续Mukaiyama-Michael加成反应，研究了O-保护的4-羟基-2-甲基环戊-2-烯-1-酮在萜类化合物合成中的应用。有效地合成了可用于类萜合成的旋光性z青烯衍生物。
• Studies towards dynamic kinetic resolution of 4-hydroxy-2-methylcyclopent-2-en-1-one and its E - O -trityloxime
  作者：Karol Michalak、Jerzy Wicha、Jacek Wójcik

  DOI：10.1016/j.tet.2016.06.047

  日期：2016.8

  Dynamic kinetic resolution through metal complex induced racemization and Candida antarctica lipase mediated enantioselective acetylation of a model hydroxy-ketone: 4-hydroxy-2-methylcyclopent-2-en-1-one and its selected derivatives, has been studied. Racemization of the hydroxy-ketone was efficiently affected by [RuCl2(cymene)]2 complex–triethylamine while Shvo's catalyst triggered an intramolecular

  研究了通过金属络合物诱导的消旋和南极假丝酵母脂肪酶介导的模型羟基酮的对映选择性乙酰化的动力学动力学拆分：4-羟基-2-甲基环戊-2-烯-1-酮及其选择的衍生物。[RuCl 2（cymene ）] 2络合物三乙胺有效地影响了羟基酮的外消旋作用，而Shvo的催化剂引发了分子内的氧化还原过程。在与[RuCl 2（cymene）] 2外消旋相容的条件下，南极衣藻的4-羟基-2-甲基环戊-2-烯-1-酮的动力学拆分未能达到效率阈值。但是，其O的动态动力学分辨率[RuCl 2（cymene ）] 2-三乙胺和南极弯曲杆菌脂肪酶-乙酸异丙烯酯的组合成功实现了对苯三甲肟。
• An Enantioselective Total Synthetic Approach to (+)-Heptemerone G and (+)-Guanacastepene A from 2-Furyl Methyl Carbinol
  作者：Jerzy Wicha、Karol Michalak

  DOI：10.1055/s-0033-1338857

  日期：——

  An enantioselective synthesis of the key bicyclic building block for (+)-heptemerone G and (+)-guanacastepene A construction has been accomplished. 2-Furyl methyl carbinol was used as the starting material and (S)-4-hydroxy-2-methylcyclopent-2-en-1-one as the primal optically active intermediate.
• Tanis, Steven P.; Robinson, Edward D.; McMills, Mark C., Journal of the American Chemical Society, 1992, vol. 114, # 22, p. 8349 - 8362
  作者：Tanis, Steven P.、Robinson, Edward D.、McMills, Mark C.、Watt, William

  DOI：——

  日期：——
• A new and efficient chemoenzymatic route to both enantiomers of α′-acetoxy-α-methyl and γ-hydroxy-α-methyl cyclic enones
  作者：Ayhan S. Demir、Hamide Fındık、Elif Köse

  DOI：10.1016/j.tetasy.2003.12.006

  日期：2004.3

  A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting alpha'-acetoxy-alpha-methyl and gamma-hydroxy-alpha-methyl cyclic enones starting from alpha-methyl-beta-methoxy cyclic enones is reported. Manganese(Ill) acetate-mediated acetoxylation followed by the enzyme-mediated hydrolysis of alpha'-acetoxy enone provides acetoxy enones 1a and 2a and hydroxy enones 1b and 2b with high enantiomeric excesses in good yields. The reduction of the acetoxy and hydroxy enones furnished both enantiomers of gamma-hydroxy-alpha-methyl cyclic enones 3 and 4 in a high enantiomeric excess. (C) 2003 Elsevier Ltd. All rights reserved.