2-乙酰基-3-苯基-l-薄荷吡唑 | 155095-22-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-乙酰基-3-苯基-l-薄荷吡唑
• 英文名称: 2-acetyl-3-phenyl-l-menthopyrazole
• 英文别名: 2-acetyl-7-isopropyl-4-methyl-3-phenyl-4,5,6,7-tetrahydro-2H-indazole；1-[(4R,7S)-4-methyl-3-phenyl-7-propan-2-yl-4,5,6,7-tetrahydroindazol-2-yl]ethanone
• CAS: 155095-22-0
• 化学式: C₁₉H₂₄N₂O
• 分子量: 296.412
• InChiKey: MTZOTXMZQHBAQM-CJNGLKHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-乙酰基-3-苯基-l-薄荷吡唑 在 乙酰氯 作用下， 生成 1-acetyl-3-phenyl-l-menthopyrazole
  参考文献：
  名称：

  一种新的手性辅助化合物的立体选择性N-酰化；3-苯基-1-薄荷脑吡唑

  摘要：

  作为具有吡唑环系统中的新的手性助剂化合物，的合成实用程序（4R，7S）-3-苯基-4-甲基-7-异丙基-4,5,6,7- tetrahydroindazole（3-苯基升-讨论了由1-薄荷酮制备的薄荷脑吡唑。

  DOI：

  10.1016/s0040-4039(00)61417-x
• 作为产物：
  描述：

  (-)-薄荷酮 在 盐酸 、 一水合肼 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 2-乙酰基-3-苯基-l-薄荷吡唑
  参考文献：
  名称：

  一种新的手性辅助化合物的立体选择性N-酰化；3-苯基-1-薄荷脑吡唑

  摘要：

  作为具有吡唑环系统中的新的手性助剂化合物，的合成实用程序（4R，7S）-3-苯基-4-甲基-7-异丙基-4,5,6,7- tetrahydroindazole（3-苯基升-讨论了由1-薄荷酮制备的薄荷脑吡唑。

  DOI：

  10.1016/s0040-4039(00)61417-x

文献信息

• Asymmetric reaction of diethylzinc with aldehydes catalyzed by <i>l</i> ‐menthopyrazole derivatives
  作者：Choji Kashima、Kohei Higashide、Yohei Miwa、Yoshihiro Tsukamoto

  DOI：10.1002/jhet.5570390511

  日期：2002.9

  N-Hydroxyalkyl-1-menthopyrazoles acted as a chiral catalyst for the diethylzinc (1) addition to aromatic aldehydes, and 1-aryl-1-propanols were afforded enantioselectively. These reactions were carried out optimally in toluene at 40 °C in the presence of 30 mol% of (2′S)-2-(2-phenyl-2-hydroxyethyl)-3-phenyl-1-men-thopyrazole ((S)-16d) to afford optically active 1-aryl-1-propanols up to 70% ee (S).

  Ñ -Hydroxyalkyl- 1 -menthopyrazoles充当用于二乙基锌（手性催化剂1）除了芳香醛和1-芳基-1-丙醇进行对映选择性地得到。这些反应在30摩尔％（2'S）-2-（2-苯基-2-羟乙基）-3-苯基-1-men-吡唑（（S）-16d），得到高达70％ee（S）的旋光1-芳基-1-丙醇。
• Resolution of secondary alcohols using 2-acyl-3-phenyl-l-menthopyrazoles as enantioselective acylating agents
  作者：Choji Kashima、Saori Mizuhara、Yohei Miwa、Yukihiro Yokoyama

  DOI：10.1016/s0957-4166(02)00472-x

  日期：2002.8

  The chelation of AlCl3 with N-acylpyrazoles leads to structural fixation of the acyl moiety and an acceleration in the rate of acylation of secondary alcohols. The chiral environment of the fixed acyl moiety of 2-acyl-3-phenyl-1-menthopyrazole 2 causes diastereofacial selectivity in the reaction with secondary alcohols, and thus 2 behaves as an enantioselective acylating agent. By the use of 2.4 molar equivalents of racemic 1-phenylethanol 3a, 2-acetyl-3-phenyl-1-menthopyrazole 2a afforded (S)-1-phenylethyl acetate (S)-4aa enantioselectively and unreacted 3a was recovered with (R)-configuration. Furthermore, the inverse configurational preferences were observed to give (R)-4aa and (S)-3a by the addition of strongly basic amines, which sometimes behaved as catalysts for enolate formation from 2 and AlCl3. These dramatic changes in stereoselective preference should be useful properties of 2-acyl-3-phenyl-1-menthopyrazole 2 as an enantioselective acylating agent. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Stereocontrolled Aldol Reaction of N-Acylpyrazoles with Aldehydes Using LDA or MgBr2-DIEA
  作者：Choji Kashima、Iwao Fukuchi、Katsumi Takahashi、Kiyoshi Fukusaka、Akira Hosomi

  DOI：10.3987/com-97-s(n)31

  日期：——

  The aldol reaction of 1-acyl-3,5-dimethylpyrazoles (1) was kinetically controlled with syn stereoselectivity through lithium enolate intermediate using LDA. On the contrary, the anti stereoselective aldol reaction of 1 was caused by the action of DIEA in the presence of MgBr2 under the thermodynamic control. in the formation of syn-aldol products using 3-phenyl-1-menthopyrazole as a chiral auxiliary, the diastereoselectivity was observed up to 81% de with the predominant configuration of 2'S form.