(2R,3S)-3-hydroxy-2-methyl-2-(2-propenyl)cyclopentan-1-one | 109120-85-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S)-3-hydroxy-2-methyl-2-(2-propenyl)cyclopentan-1-one
• 英文别名: (2R,3S)-3-hydroxy-2-methyl-2-(3-propenyl)cyclopentanone；(2R,3S)-3-Hydroxy-2-methyl-2-(prop-2-enyl)-cyclopentanon；(2R,3S)-2-allyl-3-hydroxy-2-methylcyclopentanone；2-allyl-3-hydroxy-2-methylcyclopentan-1-one；(2R,3S)-3-hydroxy-2-methyl-2-prop-2-enylcyclopentan-1-one
• CAS: 109120-85-6
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: DKKOSAKIPMMIFY-IONNQARKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (2R,3S)-3-hydroxy-2-methyl-2-(2-propenyl)cyclopentan-1-one 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 为溶剂， 生成 (2R,3S)-3-Hydroxy-2-methyl-2-propyl-cyclopentanon
  参考文献：
  名称：

  Asymmetric microbial reduction of prochiral 2,2,-disubstituted cycloalkanediones

  摘要：

  DOI：

  10.1021/jo00391a009
• 作为产物：
  描述：

  2-甲基-1,3-环戊二酮 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 27.0h， 生成 (2R,3S)-3-hydroxy-2-methyl-2-(2-propenyl)cyclopentan-1-one
  参考文献：
  名称：

  Asymmetric microbial reduction of prochiral 2,2,-disubstituted cycloalkanediones

  摘要：

  DOI：

  10.1021/jo00391a009

文献信息

• Stereoselective Reduction of Prochiral Cyclic 1,3-Diketones Using Different Biocatalysts
  作者：Martina Letizia Contente、Federica Dall’Oglio、Francesca Annunziata、Francesco Molinari、Marco Rabuffetti、Diego Romano、Lucia Tamborini、Dörte Rother、Andrea Pinto

  DOI：10.1007/s10562-019-03015-y

  日期：2020.4

  biocatalytic methods for the stereoselective reduction of cyclic prochiral 1,3-diketones for the production of optically active β -hydroxyketones and/or 1,3-diols. The recombinant ketoreductase KRED1-Pglu (formulated as purified catalyst) and whole cells of wild type Escherichia coli DE3 Star were used as biocatalysts, displaying different and sometimes complementary stereoselectivity, thus allowing the preparation

  摘要 我们开发了立体选择性还原环状前手性 1,3-二酮的生物催化方法，用于生产光学活性 β-羟基酮和/或 1,3-二醇。重组酮还原酶 KRED1-Pglu（配制为纯化催化剂）和野生型大肠杆菌 DE3 Star 的全细胞用作生物催化剂，显示出不同且有时互补的立体选择性，从而允许制备立体化学纯的 β-羟基酮（12-66% 分离）产率，> 99% ee）和 1,3-二醇（40–60% 分离产率，> 99% ee）。图形摘要
• Efforts toward rapid construction of the cortistatin A carbocyclic core via enyne-ene metathesis
  作者：Corinne Baumgartner、Sandy Ma、Qi Liu、Brian M. Stoltz

  DOI：10.1039/c004275g

  日期：——

  Our efforts toward the construction of the carbocylic core of cortistatin A via an enyne-ene metathesis are disclosed. Interestingly, an attempted SN2 inversion of a secondary mesylate in our five-membered D-ring piece gave a product with retention of stereochemistry.

  我们致力于通过烯炔来构建皮质抑素A的糖核核心，烯复分解公开。有趣的是，一次S N 2的反演尝试甲磺酸酯 在我们的五元D形环件中，产品保留了立体化学特性。
• Structure-Guided Directed Evolution of a Carbonyl Reductase Enables the Stereoselective Synthesis of (2<i>S</i>,3<i>S</i>)-2,2-Disubstituted-3-hydroxycyclopentanones via Desymmetric Reduction
  作者：Juan Li、Jinhui Feng、Xi Chen、Jingyao Gong、Yunfeng Cui、Hongliu Zhang、Dandan Bu、Qiaqing Wu、Dunming Zhu

  DOI：10.1021/acs.orglett.0c00892

  日期：2020.5.1

  In this study, an engineered carbonyl reductase (M4) was obtained through structure-guided directed evolution of a carbonyl reductase (SSCR) from Sporobolomyces salmonicolor AKU4429. Mutant M4 showed 23.9-fold enhancement of enzyme activity toward the model substrate 2-methyl-2-benzyl-1,3-cyclopentanedione, affording the (2S,3S)-stereoisomer in >98% ratio. This variant also showed excellent stereoselectivity

  在这项研究中，工程改造的羰基还原酶（M4）是通过结构引导的鲑鱼孢菌AKU4429羰基还原酶（SSCR）的定向进化而获得的。突变体M4对模型底物2-甲基-2-苄基-1,3-环戊二酮显示出23.9倍的酶活性增强，提供（2S，3S）-立体异构体的比率> 98％。该变体对大多数测试底物也显示出优异的立体选择性，为有价值的生物催化剂提供了立体选择性地还原这些环状二酮以接近相应的（2S，3S）-2,2-二取代-3-羟基酮的生物催化剂。
• Directed evolution of an alcohol dehydrogenase for the desymmetric reduction of 2,2-disubstituted cyclopenta-1,3-diones by enzymatic hydrogen transfer
  作者：Hongliu Zhang、Liangyan Zhu、Jinhui Feng、Xiangtao Liu、Xi Chen、Qiaqing Wu、Dunming Zhu

  DOI：10.1039/d2cy00559j

  日期：——

  Chiral 2,2-disubstituted 3-hydroxycycloketones are highly desired intermediates for the construction of complex molecules with multiple chiral centres. Structure-guided directed evolution of the alcohol dehydrogenase TbADH from Thermoanaerobacter brockii was performed to enhance the enzyme activity toward ethyl secodione (1a) in an attempt to use isopropanol for substrate-coupling cofactor regeneration

  手性 2,2-二取代 3-羟基环酮是构建具有多个手性中心的复杂分子的非常理想的中间体。对来自布氏嗜热杆菌的乙醇脱氢酶 TbADH进行结构引导的定向进化，以增强酶对乙基二甲双胍 ( 1a ) 的活性，以尝试使用异丙醇进行底物偶联辅因子再生。调节底物隧道和活性中心中的氨基酸残基导致突变体 Tb2 (N114G/L294P)、Tb3 (N114G/M285L/L294P) 和 Tb4 (W110V/N114G/M285L/L294P) 对1a的活性提高，但活性降低对于异丙醇。突变体 Tb2 催化1a还原生成(13 R ,17使用异丙醇再生 NADPH，收率 94% 和 >99.5% ee 和 de 的S )-乙基 secol。然而，底物偶联 NADPH 再生对变体 Tb3 和 Tb4 无效，因为它们对异丙醇的活性较低。突变体 Tb2 和 Tb3 对一系列 2-methyl-2-benzyl-cyclopenta-1
• Diastereoselective reduction of β-keto carbonyl compounds by cultured plant cells
  作者：Kei Shimoda、Naoji Kubota、Hatsuyuki Hamada、Hiroki Hamada

  DOI：10.1016/j.tetlet.2006.01.005

  日期：2006.3

  The diastereoselective reduction of beta-keto carbonyl compounds such as 2-benzamidomethyl-3-oxobutanoates and 2-methyl-2-(2-propenyl)cyclopentan-1,3-dione by cultured cells of higher plants was investigated. The reduction of the 2-benzamidomethyl-3-oxobutanoates by Parthenocissus tricitspidata diastercoselectively produced the (2R,3S)-2-benzamidomethyl-3-hydroxybutanoates, whereas the reduction by Gossypium hirsultum gave the (2S,3S)-2-benzimidoinethyl-3-hydroxybutanoates. The (2R,3S)l (2S,3S) predominance in the reduction with Nicotiana tabacum, Glycine max, and Catharan thus roseus was reversed by the change in the structure of the alkoxyl group in the substrate. On the other hand, the reduction of 2-methyl-2-(2-propenyl)cyclopelitan-1,3-dione by P. tricuspidata produced (2R,3S)-3-hydroxy-2-methyl-2-(2-propenyl)cyclopent in-1-one, whereas the reaction by N. tabacum, G. max, C roseus' and G. hirsuatum gave (2S,3S)-3-hydroxy-2-methyl-2-(2-propenyl)cyclopentan-1-one. (c) 2006 Elsevier Ltd. All rights reserved.