(3bR,4aR)-2-(3,4,4-trime-3b,4,4a,5-tetrahydrocyclopropa[3,4]cyclopenta[1,2-c]pyrazol-1-yl)-ethanol | 200882-13-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (3bR,4aR)-2-(3,4,4-trime-3b,4,4a,5-tetrahydrocyclopropa[3,4]cyclopenta[1,2-c]pyrazol-1-yl)-ethanol
• 英文别名: 2-[(3bS,4aR)-3,4,4-trimethyl-3b,4,4a,5-tetrahydro-1H-cyclopropa[3,4]cyclopenta[1,2-c]pyrazol-1-yl]ethanol；2-[(2S,4R)-3,3,9-trimethyl-7,8-diazatricyclo[4.3.0.02,4]nona-1(6),8-dien-7-yl]ethanol
• CAS: 200882-13-9
• 化学式: C₁₂H₁₈N₂O
• 分子量: 206.288
• InChiKey: ZONATEUBOAGVSK-LDYMZIIASA-N

物化性质

• 沸点：
  335.2±30.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  水 、 三丁氧基氧化钒 、 (3bR,4aR)-2-(3,4,4-trime-3b,4,4a,5-tetrahydrocyclopropa[3,4]cyclopenta[1,2-c]pyrazol-1-yl)-ethanol 以 二氯甲烷 为溶剂， 以99%的产率得到[VO2((3bR,4aR)-2-(3,4,4-trimethyl-3b,4,4a,5-tetrahydrocyclopropa[3,4]cyclopenta[1,2-c]pyrazol-1-yl)-ethanol)(n-BuOH)]
  参考文献：
  名称：

  Stereoselective oxidation of linalool with tert-butyl hydroperoxide, catalyzed by a vanadium(V) complex with a chiral terpenoid ligand

  摘要：

  Stereoselective epoxidation of (-)-(R)-linalool by tert-butylhydroperoxide (TBHP) catalyzed by a vanadium(V) complex formed by interaction of [VO(acac)(2)] or [VO(On-Bu)(3)] with a new chiral terpenoid ligand (L) is reported. Moderate diastereomeric excess (de 56%) was attained in toluene at 20 degreesC. V-51, C-13 and O-17 NMR spectroscopic monitoring of the studied catalytic system showed that a new complex 1 forms quantitatively upon interaction of [VO(On-Bu)(3)] with L in CH2O2. Compound 1 is a mononuclear complex of vanadium(V), which incorporates the tridentate chiral ligand L, as well as V=O moieties. It has been shown that TBHP binds to 1 giving a 1.TBHP adduct with the association constant K = 1.36 +/- 0.111 mol(-1) at room temperature and enthalpy Delta(r) H-298(0) = -6.5 +/- 2.0 kJ mol(-1) and entropy Delta(r) S-298(0) = -20 +/- 6 J mol(-1) K-1. These 29 thermodynamic parameters are typical for outer sphere complexes (OSCs). Adduct 1 .TBHP is suggested to be a precursor of the active intermediate of the stereoselective epoxidation process. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s1381-1169(02)00527-7
• 作为产物：
  描述：

  2-肼基乙醇 、 (1R,5R)-2-Acetyl-6,6-dimethyl-bicyclo[3.1.0]hexan-3-one 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以66%的产率得到(3bR,4aR)-2-(3,4,4-trime-3b,4,4a,5-tetrahydrocyclopropa[3,4]cyclopenta[1,2-c]pyrazol-1-yl)-ethanol
  参考文献：
  名称：

  Synthesis of new chiral N-substituted fused pyrazoles and pyrazolinols

  摘要：

  Treatment of beta-diketones and the corresponding beta-enaminoketones, having modified carane (2-ethyl-6,6-dimethylbicyclo[3.1.0]hexane) and p-menthane (3-ethyl-1-isopropylcyclopentane) skeletons, with aryl-and alkylhydrazines results in regioselective formation of N-substituted pyrazoles or stable pyrazolinols depending on the nature of the substituent at the hydrazine nitrogen. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10239-3

文献信息

• Synthesis of new chiral N-substituted fused pyrazoles and pyrazolinols
  作者：Sergey A. Popov、Makhmut M. Shakirov、Alexey V. Tkachev、Norbert De Kimpe

  DOI：10.1016/s0040-4020(97)10239-3

  日期：1997.12

  Treatment of beta-diketones and the corresponding beta-enaminoketones, having modified carane (2-ethyl-6,6-dimethylbicyclo[3.1.0]hexane) and p-menthane (3-ethyl-1-isopropylcyclopentane) skeletons, with aryl-and alkylhydrazines results in regioselective formation of N-substituted pyrazoles or stable pyrazolinols depending on the nature of the substituent at the hydrazine nitrogen. (C) 1997 Elsevier Science Ltd.
• Stereoselective oxidation of linalool with tert-butyl hydroperoxide, catalyzed by a vanadium(V) complex with a chiral terpenoid ligand
  作者：K.P Bryliakov、E.P Talsi、S.N Stas’ko、O.A Kholdeeva、S.A Popov、A.V Tkachev

  DOI：10.1016/s1381-1169(02)00527-7

  日期：2003.3

  Stereoselective epoxidation of (-)-(R)-linalool by tert-butylhydroperoxide (TBHP) catalyzed by a vanadium(V) complex formed by interaction of [VO(acac)(2)] or [VO(On-Bu)(3)] with a new chiral terpenoid ligand (L) is reported. Moderate diastereomeric excess (de 56%) was attained in toluene at 20 degreesC. V-51, C-13 and O-17 NMR spectroscopic monitoring of the studied catalytic system showed that a new complex 1 forms quantitatively upon interaction of [VO(On-Bu)(3)] with L in CH2O2. Compound 1 is a mononuclear complex of vanadium(V), which incorporates the tridentate chiral ligand L, as well as V=O moieties. It has been shown that TBHP binds to 1 giving a 1.TBHP adduct with the association constant K = 1.36 +/- 0.111 mol(-1) at room temperature and enthalpy Delta(r) H-298(0) = -6.5 +/- 2.0 kJ mol(-1) and entropy Delta(r) S-298(0) = -20 +/- 6 J mol(-1) K-1. These 29 thermodynamic parameters are typical for outer sphere complexes (OSCs). Adduct 1 .TBHP is suggested to be a precursor of the active intermediate of the stereoselective epoxidation process. (C) 2002 Elsevier Science B.V. All rights reserved.