(3R,6S)-2-Benzoyl-3-methyl-6-isopropylcyclohexanone | 155095-12-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,6S)-2-Benzoyl-3-methyl-6-isopropylcyclohexanone
• 英文别名: (3R,6S)-2-benzoyl-6-isopropyl-3-methylcyclohexanone；2-Benzoylmenthon；(3R,6S)-2-benzoyl-3-methyl-6-propan-2-ylcyclohexan-1-one
• CAS: 155095-12-8
• 化学式: C₁₇H₂₂O₂
• 分子量: 258.36
• InChiKey: VPTKSNILIUZETI-JEIKQXNFSA-N

物化性质

• 沸点：
  377.8±35.0 °C(Predicted)
• 密度：
  1.024±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,6S)-2-Benzoyl-3-methyl-6-isopropylcyclohexanone 在 盐酸 、 一水合肼 、 三乙胺 作用下， 生成 2-pivaloyl-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：

  L-薄荷醇 在 silica gel 、 pyridinium chlorochromate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 (3R,6S)-2-Benzoyl-3-methyl-6-isopropylcyclohexanone
  参考文献：
  名称：

  Diastereoselective Aziridination of Chiral Electron-Deficient Olefins with N-Chloro-N-sodiocarbamates Catalyzed by Chiral Quaternary Ammonium Salts

  摘要：

  Chiral quaternary ammonium salt-catalyzed diastereoselective aziridination of electron-deficient olefins that possess a chiral auxiliary with N-chloro-N-sodiocarbamates was developed. The key to high stereoselectivity was found to be the employment of the "matching" stereochemical combination of chiral auxiliary/ammonium salt. For example, when 3-phenyl-(4R,7S)-4-methyl-7-isopropyl-4,S,6,7-tetrahydroindazole (L-menthopyrazole) as a chiral auxiliary and a cinchonidine-derived chiral ammonium salt as a catalyst were applied to the reaction system, perfect diastereoselectivity was realized. Furthermore, the preparation of enantiomerically pure aziridines by removal of the chiral auxiliary was demonstrated.

  DOI：

  10.1021/jo2010632

文献信息

• Asymmetric borane reduction of ketones promoted by menthopyrazole-zncl₂complex
  作者：Choji Kashima、Yoshihiro Tsukamoto、Yohei Miwa、Kohei Higashide

  DOI：10.1002/jhet.5570380308

  日期：2001.5

  The enantioselective reduction of ketones was accomplished by borane in the presence of pyrazole derivatives, particularly 2-methoxymethyl-3-phenyl-1-menthopyrazole (8). The catalysis of zinc chloride makes it possible to lower the reaction temperature below 0 °C, and to promote enantioselectivity.

  在吡唑衍生物，特别是2-甲氧基甲基-3-苯基-1-薄荷基吡唑（8）的存在下，通过硼烷完成对映体酮的对映选择性还原。氯化锌的催化使得可以将反应温度降低至低于0℃，并促进对映选择性。
• Preparation of 2,6-bis(<i>l</i>-menthopyrzol-3-yl)pyridines and their catalytic activity for asymmetric diels alder reaction
  作者：Choji Kashima、Saori Shibata、Hiroyo Yokoyama、Takehiko Nishio

  DOI：10.1002/jhet.5570400505

  日期：2003.9

  of 3-phenyl-l-menthopyrazole (1b) and C2 symmetric ligand in the molecule, should form the C2 symmetric complex in situ with Zn(OTf)2 or Ni(ClO4)2•6H2O. The subsequent complex catalyzed the Diels Alder reaction of 1-acryloyl-3,5-dimethylpyrazole (11a) with cyclopentadiene (12) enantioselectively up to 75 % ee.

  由1-薄荷酮制备3-芳基-1-薄荷脑吡唑1和2及相关化合物，并讨论了它们的对映选择性活性作为手性配体。在这一系列化合物中，具有3-苯基-1-薄荷脑吡唑（1b）和C 2对称配体的结构特征的2,6-双（2-甲基-1-薄荷脑吡唑-3-基）吡啶（8a）在分子中，应与Zn（OTf）2或Ni（ClO 4）2 •6H 2原位形成C 2对称络合物O.随后的络合物催化1-丙烯酰基-3，5-二甲基吡唑（11a）与环戊二烯（12）的对映选择性Diels Alder反应，对映体选择性高达75％ee。
• Diastereoselective .alpha.-Alkylation of 2-Acyl-3-phenyl-l-menthopyrazoles
  作者：Choji Kashima、Iwao Fukuchi、Akira Hosomi

  DOI：10.1021/jo00104a045

  日期：1994.12

  N-Acylpyrazoles were alpha-alkylated in good yields by the treatment with alkyl halides after metalation with LDA or LiHMDS, In the case of chiral N-acylpyrazoles, e.g., 2-acyl-3-phenyl-l-menthopyrazoles (4), the alpha-alkylation was highly diastereoselective. The subsequent alpha-alkylation products could be converted into esters in good yield in the presence of BF3.OEt(2) without the loss of the optical purity.
• Diastereoselective Aziridination of Chiral Electron-Deficient Olefins with <i>N</i>-Chloro-<i>N</i>-sodiocarbamates Catalyzed by Chiral Quaternary Ammonium Salts
  作者：Yuta Murakami、Youhei Takeda、Satoshi Minakata

  DOI：10.1021/jo2010632

  日期：2011.8.5

  Chiral quaternary ammonium salt-catalyzed diastereoselective aziridination of electron-deficient olefins that possess a chiral auxiliary with N-chloro-N-sodiocarbamates was developed. The key to high stereoselectivity was found to be the employment of the "matching" stereochemical combination of chiral auxiliary/ammonium salt. For example, when 3-phenyl-(4R,7S)-4-methyl-7-isopropyl-4,S,6,7-tetrahydroindazole (L-menthopyrazole) as a chiral auxiliary and a cinchonidine-derived chiral ammonium salt as a catalyst were applied to the reaction system, perfect diastereoselectivity was realized. Furthermore, the preparation of enantiomerically pure aziridines by removal of the chiral auxiliary was demonstrated.
• Stereoselective N-acylation of a new chiral auxiliary compound; 3-phenyl-l-menthopyrazole
  作者：Choji Kashima、Iwao Fukuchi、Katsumi Takahashi、Akira Hosomi

  DOI：10.1016/s0040-4039(00)61417-x

  日期：1993.12

  As a new chiral auxiliary compound having a pyrazole ring system, the synthetic utility of (4R,7S)-3-phenyl-4-methyl-7-isopropyl-4,5,6,7-tetrahydroindazole (3-phenyl-l-menthopyrazole), which was prepared from l-menthone, was discussed.

  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。