(R)-(+)-3-Propylcyclohexanone | 73959-35-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-(+)-3-Propylcyclohexanone
• 英文别名: (3R)-3-propylcyclohexan-1-one
• CAS: 73959-35-0
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: JTWWWMMYLTUDHS-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-(+)-3-Propylcyclohexanone 在 HLAD-NADH 作用下， 以 乙醇 、 水 为溶剂， 生成 (1S,3R)-3-n-propylcyclohexanol
  参考文献：
  名称：

  Osselaer, T. A. Van; Lemiere, G. L.; Lepoivre, J. A., Bulletin des Societes Chimiques Belges, 1980, vol. 89, # 2, p. 133 - 150

  摘要：

  DOI：
• 作为产物：
  描述：

  3-丙基环己酮 生成 (R)-(+)-3-Propylcyclohexanone
  参考文献：
  名称：

  Osselaer, T. A. Van; Lemiere, G. L.; Lepoivre, J. A., Bulletin des Societes Chimiques Belges, 1980, vol. 89, # 2, p. 133 - 150

  摘要：

  DOI：

文献信息

• Catalytic asymmetric conjugate addition of grignard reagents mediated by copper(I)-chiral bidentate phosphine complex
  作者：Motomu Kanai、Kiyoshi Tomioka

  DOI：10.1016/0040-4039(95)00759-6

  日期：1995.6

  A catalytic amount of a chiral phosphine 1-copper iodide complex catalyzes the conjugate addition of organomagnesium chlorides to cycloalkenones and pentenolide to give the corresponding addition products in 94-72% ee.

  催化量的手性膦1-铜碘化物配合物催化有机氯化镁与环烯酮和戊烯内酯的共轭加成，从而得到94-72％ee的相应加成产物。
• Catalytic enantioselective conjugate addition of Grignard reagents to cyclic α,β-unsaturated carbonyl compounds
  作者：Motomu Kanai、Yuichi Nakagawa、Kiyoshi Tomioka

  DOI：10.1016/s0040-4020(99)00095-2

  日期：1999.3

  A catalytic asymmetric conjugate addition reaction of organocopper reagents, generated from copper salt, a chiral phosphine, and Grignard reagent, with cyclohexenone is highly dependent on the counter anion of copper species, solvents, Grignard reagents, and the structure of the chiral phosphine. The reaction using the combination of 8 mol% of copper iodide, 32 mol% of the amidophosphine 3, and 1.2

  由铜盐，手性膦和格氏试剂与环己烯酮产生的有机铜试剂的催化不对称共轭加成反应高度依赖于铜离子，溶剂，格氏试剂和手性膦结构的抗衡阴离子。在-78°C下，使用8摩尔％的碘化铜，32摩尔％的氨基膦3和1.2当量的有机氯化镁与环己烯酮在乙醚中的混合物进行反应，得到3-取代的环己酮，其ee最高为92％，ee为90 ％ 屈服。
• Highly Enantio- and s-trans CC Bond Selective Catalytic Hydrogenation of Cyclic Enones: Alternative Synthesis of (−)-Menthol
  作者：Takashi Ohshima、Hiroshi Tadaoka、Kiyoto Hori、Noboru Sayo、Kazushi Mashima

  DOI：10.1002/chem.200701505

  日期：2008.2.27

  % ee). To obtain high enantio- and s-trans selectivities, the addition of a halogen source to the cationic Rh complex was the essential step. With the key step of the s-trans selective asymmetric hydrogenation of piperitenone, we demonstrated a new synthetic method for optically pure (-)-menthol via three atom-economical hydrogenations. Moreover, we found that the complete s-trans and s-cis C=C bond

  通过使用阳离子Rh（I）配合物，（S）-5,5'-双di（3,5-二叔丁基-4-甲氧基苯基膦基） } -4,4'-bi-1,3-苯并二甲苯（DTBM-SEGPHOS）和（CH2CH2PPh3Br）2。环状烯酮上s-顺式C ＝ C键异亚丙基部分的存在影响氢化的对映选择性。因此，同时包含s-顺式和s-反式烯酮的3-烷基-6-异亚丙基-2-环己烯-1-酮的氢化以优异的对映选择性（至多98％ee）进行。为了获得高对映体和s-反式选择性，将卤素源添加到阳离子Rh络合物中是必不可少的步骤。在哌啶酮的反式选择性不对称加氢的关键步骤中，我们展示了一种通过三个原子经济的氢化反应制备光学纯的（-）-薄荷醇的新合成方法。此外，我们发现，完整s-反和s-顺C = C键的选择性的反应也是由手性配体和卤化物两者的适当选择来实现。
• Asymmetric induction in manganese(III)-based oxidative free-radical cyclizations of phenylmenthyl acetoacetates and 2,5-dimethylpyrrolidine acetoacetamides
  作者：Qingwei Zhang、Raju M. Mohan、Laura Cook、Sophia Kazanis、Daniel Peisach、Bruce M. Foxman、Barry B. Snider

  DOI：10.1021/jo00079a006

  日期：1993.12

  Mn(III)-based oxidative free-radical cyclization of phenylmenthyl ester 1e afforded 90% of 13 with 86% de. Cyclization of 31b provided 56% of (+)-podocarpic acid precursor 32e with 82% de. The direction of de was opposite in these two cases. Oxidative cyclization of a-methyl beta-keto ester 44b gave a 1:1.6 mixture of 46b and 47b while alpha-propyl beta-keto ester 44d produced a > 10:1 mixture of 46d and 47d indicating that the extent and direction of de is dependent on the size of the alpha-substituent The reaction proceeds through transition states 12 and 56 with large alpha-substituents and through transition states 19 and 57 with small a-substituents. The de depends on the double-bond substitution pattern as shown by the decreased de with 37b and 37d, and selectivity in the 5-exo cyclization of 64b, 65b, 70b, and 71b is low.
• Osselaer, T. A. Van; Lemiere, G. L.; Lepoivre, J. A., Bulletin des Societes Chimiques Belges, 1980, vol. 89, # 2, p. 133 - 150
  作者：Osselaer, T. A. Van、Lemiere, G. L.、Lepoivre, J. A.、Alderweireldt, F. C.

  DOI：——

  日期：——