(1S,2S)-2-bromocyclopentan-1-ol | 122673-92-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S)-2-bromocyclopentan-1-ol
• 英文别名: (1S,2S)-2-bromocyclopentanol；trans-2-Brom-cyclopentan-1-ol
• CAS: 122673-92-1
• 化学式: C₅H₉BrO
• 分子量: 165.03
• InChiKey: BQVWZYQFAVLQKE-WHFBIAKZSA-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：

  (1S,2S)-2-bromocyclopentan-1-ol 、 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 甲醇 、 (S,S,S)-tri(2-propanol)amine-zirconium 、 Dowex 30 、 3-溴丙烯 作用下， 以 氯苯 为溶剂， 反应 48.0h， 生成 (1S,2S)-2-bromocyclopentan-1-ol
  参考文献：
  名称：

  Desymmetrization of Meso Epoxides with Halides:  A New Catalytic Reaction Based on Mechanistic Insight

  摘要：

  DOI：

  10.1021/ja981031l

文献信息

• Asymmetric Synthesis using Organoboranes. Relative Effectiveness of the B-Halobis(terpenyl)boranes for the Enantioselective Halogenative Cleavage of Representative meso-Epoxides
  作者：Chandra D. Roy、Herbert C. Brown

  DOI：10.1071/ch07118

  日期：——

  A comparative study of the relative effectiveness of various Ter2BX, such as dEap2BX, lEap2BX, 2-dIcr2BX, 4-dIcr2BX, and lCleap2BX along with dIpc2BX for the asymmetric ring opening of three representative meso-epoxides (cyclohexene, cyclopentene, and cis-2,3-butene oxides) is reported. Among all the reagents studied, 2-dIcr2BCl (78–80%) demonstrated significant improvement in enantiomeric excess over

  比较研究各种 Ter2BX，如 dEap2BX、lEap2BX、2-dIcr2BX、4-dIcr2BX 和 lCleap2BX 以及 dIpc2BX 对三种代表性中间环氧化物（环己烯、环戊烯和 cis-2）的不对称开环的相对有效性,3-丁烯氧化物）被报道。在所研究的所有试剂中，2-dIcr2BCl (78–80%) 与先前探索的试剂 dIpc2BCl (41%) 相比，对映体过量有显着改善，特别是对于内消旋环己烯氧化物。尽管所有这三种试剂 dIpc2BBr、dEap2BBr 和 2-dIcr2BBr 都从内消旋环己烯氧化物中提供了相当的对映体富集的 2-溴环己烷-1-醇 (76-86%)，但基于芳烃的试剂 2-dIcr2BBr 在内消旋环戊烯氧化物 (67%) 和内消旋顺式 2 的对映体过量，3-氧化丁烯 (78%) 比使用先前报道的试剂 dIpc2BBr (分别为 57% 和 61%)
• Asymmetric ring opening of meso-epoxides with B-halobis(2-isocaranyl)boranes 2-dIcr2BX
  作者：Chandra D. Roy、Herbert C. Brown

  DOI：10.1016/j.tetasy.2006.06.044

  日期：2006.8

  Hydroboration of commercially available (+)-2-carene (96% ee) with either BH2Cl center dot SMe2 or BC13/Me3SiH, provides chemically pure B-chlorobis(2-isocaranyl)borane (2-(d)Icr(2)BCl) whereas B-bromobis(2-isocaranyl)borane (2-(d)Icr(2)BBr) could only be prepared by Matteson's BBr3/Me3SiH procedure in high chemical yield and purity. The enantionteric excess achieved with 2-(d)Icr(2)BCl (78%), was significantly higher than those realized with the previously explored reagent, (IPC2BCl)-I-d (41%), especially for meso-cyclohexene oxide. The new reagent, 2-(d) Icr(2)BBr also showed considerable improvements in enantiomeric excesses, in the cases of meso-cyclopentene oxide (67%) and meso-cis-2,3-butene oxide (78%) than those achieved with the previously reported reagent, (IPC2BBr)-I-d (57% and 61%, respectively). (c) 2006 Elsevier Ltd. All rights reserved.
• STORK, GILBERT;KEITZ, PAUL F., TETRAHEDRON LETT., 30,(1989) N0, C. 6981-6984
  作者：STORK, GILBERT、KEITZ, PAUL F.

  DOI：——

  日期：——
• 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.
• Desymmetrization of Meso Epoxides with Halides:  A New Catalytic Reaction Based on Mechanistic Insight
  作者：William A. Nugent

  DOI：10.1021/ja981031l

  日期：1998.7.1