(1S,2S)-2-iodocyclopentanol | 122673-93-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S)-2-iodocyclopentanol
• 英文别名: trans-2-Iod-cyclopentan-1-ol；(1S,2S)-2-iodocyclopentan-1-ol
• CAS: 122673-93-2
• 化学式: C₅H₉IO
• 分子量: 212.03
• InChiKey: TVKJMPYMACHDDR-WHFBIAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,2S)-2-iodocyclopentanol 、 甲氧基-三氟甲基苯 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Enzymatic preparation of (1S,2R)- and (1R,2S)-stereoisomers of 2-halocycloalkanols

  摘要：

  The stereoisomers of cis-2-halocycloalkanols were resolved by a kinetically controlled transesterification with vinyl acetate in the presence of lipases in organic media. High enantioselectivities (ee >98%) and good isolated yields were obtained for all substrates using the appropriate lipase. Burkholderia cepacia lipase was the most efficient enzyme for the resolution of these substrates. The enantiomeric purities of the compounds were defined by derivatization with Mosher's acid and the absolute configurations were determined by chemical correlation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.11.011
• 作为产物：
  描述：

  1,2-环氧环戊烷 在 Burkholderia cepacia Amano PS lipase 、 水 、 lithium iodide 作用下， 以 甲基叔丁基醚 为溶剂， 反应 15.0h， 生成 (1S,2S)-2-iodocyclopentanol
  参考文献：
  名称：

  Enzymatic preparation of (1S,2R)- and (1R,2S)-stereoisomers of 2-halocycloalkanols

  摘要：

  The stereoisomers of cis-2-halocycloalkanols were resolved by a kinetically controlled transesterification with vinyl acetate in the presence of lipases in organic media. High enantioselectivities (ee >98%) and good isolated yields were obtained for all substrates using the appropriate lipase. Burkholderia cepacia lipase was the most efficient enzyme for the resolution of these substrates. The enantiomeric purities of the compounds were defined by derivatization with Mosher's acid and the absolute configurations were determined by chemical correlation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.11.011

文献信息

• Simple, Catalytic Enantioselective Syntheses of Estrone and Desogestrel
  作者：Qi-Ying Hu、Pankaj D. Rege、E. J. Corey

  DOI：10.1021/ja048808x

  日期：2004.5.1

  Highly enantioselective and very short syntheses of the bioactive forms of estrone (3) and desogestrel (4) are described using a chiral oxazaborolidinium catalyst (2) in the key initial step. Enantiomerically pure estrone was synthesized in eight steps from the readily available starting materials diene 5 and alpha,beta-enal 6 via intermediates 8 and 9. Desogestrel was synthesized using a similar strategy

  在关键的初始步骤中使用手性 oxazaborolidinium 催化剂 (2) 描述了雌酮 (3) 和去氧孕烯 (4) 的生物活性形式的高度对映选择性和非常短的合成。对映异构纯雌酮是从容易获得的起始材料二烯 5 和 α,β-烯醛 6 经中间体 8 和 9 合成的，分八步合成。使用类似的策略从二烯 5 和 α,β-烯醛 11 经中间体 12-合成去氧孕烯17. 还介绍了手性催化剂 2 及其对映异构体的有效合成。