(S)-2-dodecanol | 91681-57-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-2-dodecanol
• 英文别名: (2S)-dodecan-2-ol
• CAS: 91681-57-1
• 化学式: C₁₂H₂₆O
• 分子量: 186.338
• InChiKey: XSWSEQPWKOWORN-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  13
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  对硝基肉桂酸 、 (S)-2-dodecanol 生成
  参考文献：
  名称：

  X-ray and Miscibility Investigations on New Compounds Exhibiting Wide Range Smectic Q Phases

  摘要：

  Four new series of liquid crystals are presented. Six of the new chiral compounds which are members of three different series exhibit wide range SmQ phases while their respective racemates and shorter homologues show SmCA, SmC and SmA phases. X-ray investigations on the SmQ phase of two compounds confirm its three-dimensional tetragonal lattice and show that the lattice parameter c can be both smaller or larger than the parameters a = b.

  DOI：

  10.1080/10587259508038708
• 作为产物：
  描述：

  正辛基镁溴盐 在 dilithium tetrachlorocuprate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 16.0h， 生成 (S)-2-dodecanol
  参考文献：
  名称：

  Pinyarat, Waraporn; Mori, Kenji, Bioscience, Biotechnology and Biochemistry, 1992, vol. 56, # 10, p. 1673

  摘要：

  DOI：

文献信息

• Enantioselective Transfer Hydrogenation of Aliphatic Ketones Catalyzed by Ruthenium Complexes Linked to the Secondary Face of β-Cyclodextrin
  作者：Alain Schlatter、Wolf-D. Woggon

  DOI：10.1002/adsc.200700558

  日期：2008.5.5

  Ruthenium-η-arene complexes attached to the secondary face of β-cyclodextrin catalyze the enantioselective reduction (ee up to 98%) of aliphatic and aromatic ketones in aqueous medium in the presence of sodium formate (HCOONa).

  在甲酸钠（HCOONa）存在下，附着在β-环糊精第二面上的钌-η-芳烃络合物催化水性介质中脂肪族和芳香族酮的对映选择性还原（ee高达98％）。
• Chiral Surfactant-Type Catalyst for Asymmetric Reduction of Aliphatic Ketones in Water
  作者：Jiahong Li、Yuanfu Tang、Qiwei Wang、Xuefeng Li、Linfeng Cun、Xiaomei Zhang、Jin Zhu、Liangchun Li、Jingen Deng

  DOI：10.1021/ja308357y

  日期：2012.11.14

  A novel chiral surfactant-type catalyst is developed. Micelles formed in water by association of the catalysts themselves, and this was confirmed by TEM analyses. Asymmetric transfer hydrogenation of aliphatic ketones catalyzed by the chiral metallomicellar catalyst gave good to excellent conversions and remarkable stereoselectivities (up to 95% ee). Synergistic effects between the metal-catalyzed

  开发了一种新型手性表面活性剂型催化剂。通过催化剂本身的结合在水中形成胶束，这通过 TEM 分析得到证实。由手性金属胶束催化剂催化的脂肪族酮的不对称转移氢化具有良好到优异的转化率和显着的立体选择性（高达 95% ee）。金属催化中心与金属胶束中核心的疏水微环境之间的协同作用导致高对映选择性。
• Palladium-catalyzed asymmetric hydrogenation of simple ketones activated by Brønsted acids
  作者：Xiao-Yu Zhou、Duo-Sheng Wang、Ming Bao、Yong-Gui Zhou

  DOI：10.1016/j.tetlet.2011.03.057

  日期：2011.6

  Homogeneous Pd(OCOCF3)2/(R)-C4-TunePhos has been successfully applied in the asymmetric hydrogenation of simple ketones activated by catalytic amount of Brønsted acid with up to 88% ee.

  均相Pd（OCOCF 3）2 /（R）-C 4 -TunePhos已成功地用于催化量不超过88％ee的布朗斯台德酸活化的简单酮的不对称氢化。
• Enantioselective Reduction of Aliphatic Ketones Using Oxazaborolidine Catalyst Generated In Situ from Chiral Lactam Alcohol and Phenoxyborane
  作者：Yasuhiro Kawanami、Yudai Mikami、Katsuhiro Hoshino、Mikiko Suzue、Izumi Kajihara

  DOI：10.1246/cl.2009.722

  日期：2009.7.5

  Oxazaborolidine catalyst generated in situ from chiral lactam alcohol 3 and p-iodophenoxyborane at room temperature was found to catalyze the enantioselective borane reduction of various prochiral ...

  发现在室温下由手性内酰胺醇 3 和对碘苯氧基硼烷原位生成的氧氮杂硼烷催化剂可催化各种前手性...
• Production of chiral alcohols from racemic mixtures by integrated heterogeneous chemoenzymatic catalysis in fixed bed continuous operation
  作者：Jose Miguel Carceller、Maria Mifsud、Maria J. Climent、Sara Iborra、Avelino Corma

  DOI：10.1039/c9gc04127c

  日期：——

  Valuable chiral alcohols have been obtained from racemic mixtures with an integrated heterogeneous chemoenzymatic catalyst in a two consecutive fixed catalytic bed continuous reactor system. In the first bed the racemic mixture of alcohols is oxidized to the prochiral ketone with a Zr-Beta zeolite and using acetone as the hydrogen acceptor. In the second catalytic bed the prochiral ketone is stereoselectively

  在两个连续的固定催化床连续反应器系统中，从与外消旋混合物与集成的非均相化学酶催化剂中获得了有价值的手性醇。在第一床中，外消旋的醇混合物用Zr-β沸石并使用丙酮作为氢受体氧化为前手性酮。在第二个催化床中，用固定在二维（2D）沸石上的醇脱氢酶（ADH）选择性立体还原前手性酮。在该方法中，第一步中通过丙酮还原而形成的醇（异丙醇）在第二步中还原了辅因子，因此整个反应循环以内部100％的经济性被内部封闭。到（R）或（S对于多种外消旋醇混合物，已经获得了醇。