tert-butyl (2S,3S)-3-cyclohexyl-3-hydroxy-2-methylpropanoate | 127422-17-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: tert-butyl (2S,3S)-3-cyclohexyl-3-hydroxy-2-methylpropanoate
• 英文别名: (2S,3S)-tert-butyl 3-cyclohexyl-3-hydroxy-2-methylpropanoate
• CAS: 127422-17-7
• 化学式: C₁₄H₂₆O₃
• 分子量: 242.359
• InChiKey: UWZZFTHJJHATDD-CMPLNLGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  tert-butyl 3-cyclohexyl-3-hydroxy-2-methylpropanoate 在 Jones’ reagent 、 tetrabutylammonium borohydride 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 1.5h， 生成 tert-butyl (2S,3S)-3-cyclohexyl-3-hydroxy-2-methylpropanoate
  参考文献：
  名称：

  氯化锰（II）或四丁基硼氢化铵催化的硼氢化钠立体选择性还原2-甲基-3-氧代酯（或酰胺）。实用的赤型和苏型-3-羟基-2-甲基酯（或酰胺）的制备方法

  摘要：

  赤-3-羟基-2- methylpropionates或赤-3-羟基-2-甲基丙酰胺用高立体选择性加入NaBH制备4减少在相应的2-甲基-3-氧代酯或2-甲基-3-氧代酰胺的催化量的氯化锰（II）的存在。另一方面，用n -Bu 4 NBH 4还原这些底物选择性地提供了苏式异构体。还描述了在1N HCl-MeOH中用NaBH 3 CN对2-甲基-3-氧代酰胺的赤型选择性还原。

  DOI：

  10.1016/s0040-4020(01)81804-4

文献信息

• High Performance of Rh(Phebox) Catalysts in Asymmetric Reductive Aldol Reaction:  High Anti-Selectivity
  作者：Hisao Nishiyama、Takushi Shiomi、Yasunori Tsuchiya、Isamu Matsuda

  DOI：10.1021/ja050698m

  日期：2005.5.1

  Chiral rhodium(bisoxazolinylphenyl) complexes (1 mol %) efficiently catalyze the asymmetric reductive aldol reaction of aldehydes and alpha,beta-unsaturated esters at 50 degrees C for ca. 0.5-1.0 h with several hydrosilanes to give the corresponding beta-hydroxypropionates with extremely high anti-selectivity (up to 98%) and enantioselectivity (up to 96% ee). The stereochemical outcome is likely due

  手性铑(双恶唑啉基苯基) 配合物 (1 mol %) 有效地催化醛和 α，β-不饱和酯在 50 摄氏度的不对称还原醛醇反应约。使用几种氢硅烷反应 0.5-1.0 小时，得到具有极高抗选择性（高达 98%）和对映选择性（高达 96% ee）的相应 β-羟基丙酸酯。立体化学结果可能是由于涉及铑-(E)-烯醇化物的椅子状循环过渡态。
• New process for enantioselective nucleophilic addition to aldehydes to form secondary alcohols
  作者：E.J. Corey、Sung Soo Kim

  DOI：10.1016/s0040-4039(00)97452-5

  日期：——

  New methodology is described for the enantioselective conversion of aldehydes to anti aldols 4 and homoallylic alcohols 7.

  新的方法是为醛以对映选择性转换描述抗醛醇4和高烯丙基醇7。
• Copper-ClickFerrophos-Complex-Catalyzed Enantioselective Reductive Aldol Reaction
  作者：Shin-ichi Fukuzawa、Minoru Kato、Hiroshi Oki、Kenichi Ogata

  DOI：10.1055/s-0029-1216724

  日期：——

  ClickFerrophos families and tested for the Cu(I)-catalyzed asymmetric reductive aldol reaction of ketones and aldehydes with an acrylic ester in the presence of phenylsilane. The Cu(I)-ClickFerrophos complex is efficient for the reaction of ketones with methyl acrylate to afford the erythro adducts both highly diastereo- and enantioselectively; the diastereomeric ratio of erythrolthreo is improved when compared

  我们已经制备了几个 ClickFerrophos 家族，并在苯基硅烷的存在下测试了酮和醛与丙烯酸酯的 Cu(I) 催化的不对称还原醛醇反应。Cu(I)-ClickFerrophos 配合物对于酮与丙烯酸甲酯的反应是有效的，以提供高度非对映选择性和对映选择性的赤型加合物；与类似的 Taniaphos 相比，erythrolthreo 的非对映体比例得到改善。
• (Diisopinocampheyl)borane-Mediated Reductive Aldol Reactions of Acrylate Esters: Enantioselective Synthesis of <i>Anti</i>-Aldols
  作者：Christophe Allais、Philippe Nuhant、William R. Roush

  DOI：10.1021/ol401679g

  日期：2013.8.2

  The (diisopinocampheyl)borane promoted reductive aldol reaction of acrylate esters 4 is described. Isomerization of the kinetically formed Z(O)-enolborinate 5Z to the thermodynamic E(O)-enolborinate 5E via 1,3-boratropic shifts, followed by treatment with representative achiral aldehydes, leads to anti-alpha-methyl-beta-hydroxy esters 9 or 10 with excellent diastereo- (up to >= 20:1 dr) and enantioselectivity (up to 87% ee). The results of double asymmetric reactions of 5E with several chiral aldehydes are also presented.
• Asymmetric Aldol Reaction with Diisopinocampheyl Enolborinates of Propionates
  作者：P. Veeraraghavan Ramachandran、Debarshi Pratihar

  DOI：10.1021/ol802850w

  日期：2009.4.2

  A convenient and general, reagent-controlled, diastereo- and enantioselective aldol reaction of diisopinocampheylboron enolates of esters, followed by reduction, has been developed as an alternative to crotylboration-ozonolysis. This protocol was then exploited for the double diastereoselective synthesis of the C11-C17 subunit of (-)-dictyostatin.