(+)-(2S,3S)-3-Hydroxy-2-methyl-2-propyl-cyclopentanon | 80888-39-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-(2S,3S)-3-Hydroxy-2-methyl-2-propyl-cyclopentanon
• 英文别名: (2S,3S)-3-hydroxy-2-methyl-2-propylcyclopentanone；cis-3-Hydroxy-2-propyl-2-methylcyclopentanone；(2S,3S)-3-hydroxy-2-methyl-2-propylcyclopentan-1-one
• CAS: 80888-39-7
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: KAJKOFDGOSLJQC-CBAPKCEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  (+)-(2S,3S)-3-Hydroxy-2-methyl-2-propyl-cyclopentanon 、 (R)-(-)-α-甲氧基-α-(三氟甲基)苯乙酰氯 以90%的产率得到
  参考文献：
  名称：

  BROOKS, D. W.;MAZDIYASNI, H.;GROTHAUS, P. G., J. ORG. CHEM., 52,(1987) N 15, 3223-3232

  摘要：

  DOI：
• 作为产物：
  描述：

  cis-(+/-)-3-hydroxy-2-methyl-2-propargylcyclopentanone 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 为溶剂， 生成 (+)-(2S,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

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
• Comparative reductive desymmetrization of 2,2-disubstituted-cycloalkane-1,3-diones
  作者：Jeremy M. Carr、Timothy S. Snowden

  DOI：10.1016/j.tet.2008.01.065

  日期：2008.3

  Reductive desymmetrization of 2-methyl-2-substituted-cycloalkane-1,3-diones can be effected using either NaBH(4) in DME or lithium tri-tert-butoxyaluminum hydride (LTBA) in THF at -60 degrees C. The former is a new approach that offers slightly greater diastereoselectivity in the reduction of 2,2-disubstituted-cyclopentane- 1,3-diones while LTBA is superior with 2,2-disubstituted-cyclohexane- 1,3-diones. Both conditions minimize subsequent reduction to diols thereby furnishing high yields of 1,3-ketols. Particularly rapid monoreductions are observed with 2-methyl-2-nitroethylcyclopentane-1,3-dione and 2-cyanoethyl-2-methylcyclopentane-1,3-dione when treated with NaBH(4) in DME at -60 degrees C. As expected, diastereoselectivity varies considerably with the substitution at C-2. (C) 2008 Elsevier Ltd. All rights reserved.
• Chiral cyclopentanoid synthetic intermediates via asymmetric microbial reduction of prochiral 2,2-disubstituted cyclopentanediones
  作者：Dee W. Brooks、Paul G. Grothaus、William L. Irwin

  DOI：10.1021/jo00135a039

  日期：1982.7
• Schwarz; Truckenbrodt; Meyer, Journal fur praktische Chemie (Leipzig 1954), 1981, vol. 323, # 5, p. 729 - 736
  作者：Schwarz、Truckenbrodt、Meyer、et al.

  DOI：——

  日期：——