(R)-(+)-2-methylcyclododecanone | 77857-75-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-(+)-2-methylcyclododecanone
• 英文别名: (R)-2-methylcyclododecanone；(2R)-2-methylcyclododecan-1-one
• CAS: 77857-75-1
• 化学式: C₁₃H₂₄O
• 分子量: 196.333
• InChiKey: JJUNXABENLJLAY-GFCCVEGCSA-N

物化性质

• 沸点：
  80-90 °C(Press: 0.1 Torr)
• 密度：
  0.855±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 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)-(+)-2-methylcyclododecanone 、 间氯过氧苯甲酸 生成 (R)-13-Methyl-oxacyclotridecan-2-one
  参考文献：
  名称：

  MEYERS A. I.; WILLIAMS D. R.; WHITE S.; ERICKSON G. W., J. AMER. CHEM. SOC., 1981, 103, NO 11, 3088-3093

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基环十二碳壬 在 高氯酸 作用下， 以 四氯化碳 为溶剂， 反应 24.0h， 生成 (R)-(+)-2-methylcyclododecanone
  参考文献：
  名称：

  Matsumoto, Kazutsugu; Tsutsumi, Seiji; Ihori, Tamiko, Journal of the American Chemical Society, 1990, vol. 112, # 26, p. 9614 - 9619

  摘要：

  DOI：

文献信息

• Cu−Catalyzed Enantioselective Conjugate Addition of Alkylzincs to Cyclic Nitroalkenes:  Catalytic Asymmetric Synthesis of Cyclic α-Substituted Ketones
  作者：Courtney A. Luchaco-Cullis、Amir H. Hoveyda

  DOI：10.1021/ja020605q

  日期：2002.7.1

  highly enantioselective (>/=92% ee) catalytic method for conjugate addition of alkylzinc reagents to cyclic nitroalkenes is reported. Reactions are promoted in the presence of 0.5-5 mol % (CuOTf)2.C6H6 and 1-10 mol % of chiral amino acid-based phosphine ligands at 0 degrees C in toluene. The Cu-catalyzed reactions can be effectively carried out with small-, medium-, and large-ring nitroalkenes. Depending

  报道了一种高效且高度对映选择性 (>/=92% ee) 的催化方法，用于将烷基锌试剂与环状硝基烯烃共轭加成。反应在 0.5-5 mol% (CuOTf)2.C6H6 和 1-10 mol% 手性氨基酸基膦配体的存在下在 0 摄氏度的甲苯中得到促进。Cu催化的反应可以与小环、中环和大环硝基烯烃有效地进行。根据所使用的反应条件，本协议可以很容易地访问硝基或相应的 α 取代酮产品。
• An asymmetric synthesis of acyclic and macrocyclic .alpha.-alkyl ketones. The role of (e)- and (z)-lithioenamines
  作者：A. I. Meyers、Donald R. Williams、Steven White、Gary W. Erickson

  DOI：10.1021/ja00401a029

  日期：1981.6
• Asymmetric Hydrogenation of Olefins with Aprotic Oxygen Functionalities Catalyzed by BINAP-Ru(II) Complexes
  作者：Tetsuo Ohta、Tsutomu Miyake、Nobuo Seido、Hidenori Kumobayashi、Hidemasa Takaya

  DOI：10.1021/jo00107a014

  日期：1995.1

  Cyclic alpha,beta-unsaturated ketones, alkylidene lactones, and alkenyl ethers have been hydrogenated in high enantiomeric excesses by use of BINAP-Ru(II) complexes (BINAP = 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) as catalysts. 2-Alkylidenecyclopentanones were hydrogenated in the presence of [RuCl(BINAP)(benzene)]Cl, Ru2Cl4(BINAP)2(NEt(3)), or Ru(OCO CH3 )(2)(BINAP) in up to 98% ee, while in the case of 2-benzylidene- and 2-(3-phenylpropylidene)cyclopentanones, enantiomeric excesses of the hydrogenation were below 50% under the same conditions. The sense of asymmetric induction as well as the enantioselectivity (95% ee) obtained in the hydrogenation of (E)-2-propylidene-gamma-butyrolactone were the same as those of the (Z)-isomer. Lactones, 2- and 4-alkylidene-gamma-butyrolactones, were converted to the corresponding saturated gamma-butyrolactones in 95% ee. Hydrogenation of diketene with the catalytic system derived from RuCl[(S)-BINAP](benzene)}Cl and triethylamine or complex Ru2Cl4[(S)-BINAP](2)(NEt(3)) established a new synthetic route to (R)-4-methyl-2-oxetanone, a promising monomer of biodegradable polymers, in up to 97% selectivity and 92% ee. Alkenyl ethers, 2-methylenetetrahydrofuran, and 2-methyl-3,4-dihydrofuran have also been hydrogenated to give 2-methyltetrahydrofuran in 91 and 87% ee, respectively.
• MATSUMOTO, KAZUTSUGU;TSUTSUMI, SEIJI;IHORI, TAMIKO;OHTA, HIROMICHI, J. AMER. CHEM. SOC., 112,(1990) N6, C. 9614-9619
  作者：MATSUMOTO, KAZUTSUGU、TSUTSUMI, SEIJI、IHORI, TAMIKO、OHTA, HIROMICHI

  DOI：——

  日期：——