cis 2-bromocyclopentanol | 20377-79-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis 2-bromocyclopentanol
• 英文别名: cis-2-bromocyclopentanol；cis-2-Bromcyclopentanol；cis-2-Hydroxycyclopentylbromid；(1S,2R)-2-Bromo-cyclopentanol；(1S,2R)-2-bromocyclopentan-1-ol
• CAS: 20377-79-1；28435-62-3；74305-04-7；87014-72-0；122673-88-5；122673-92-1
• 化学式: C₅H₉BrO
• 分子量: 165.03
• InChiKey: BQVWZYQFAVLQKE-UHNVWZDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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：

  cis 2-bromocyclopentanol 在 吡啶 、 Burkholderia cepacia Amano PS lipase 作用下， 以 四氢呋喃 、 甲基叔丁基醚 为溶剂， 反应 16.0h， 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：

  2-bromocyclopentanone 在 sodium tetrahydroborate 、 Burkholderia cepacia Amano PS lipase 作用下， 以 甲醇 、 甲基叔丁基醚 为溶剂， 反应 16.0h， 生成 cis 2-bromocyclopentanol
  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

• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Sn: Org.Comp.12, 1.4.1.1.1.5.2.1.7, page 69 - 97
  作者：

  DOI：——

  日期：——
• Reactions dh́alohydrines cyclaniques avec des alcoxytriorganoetains
  作者：Bernard Delmond、Jean-Claude Pommier

  DOI：10.1016/s0040-4039(00)70815-x

  日期：——
• Halogénoalcoxyétains
  作者：Bernard Delmond、Jean-Claude Pommier、Jacques Valade

  DOI：10.1016/s0022-328x(00)86886-2

  日期：1972.2
• Enzymatic preparation of (1S,2R)- and (1R,2S)-stereoisomers of 2-halocycloalkanols
  作者：Olga O. Kolodiazhna、Anastasy O. Kolodiazhna、Oleg I. Kolodiazhnyi

  DOI：10.1016/j.tetasy.2012.11.011

  日期：2013.1

  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.