(2RS,3SR)-3-cyclohexyl-3-hydroxy-N,N,2-trimethylpropanamide | 138201-37-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2RS,3SR)-3-cyclohexyl-3-hydroxy-N,N,2-trimethylpropanamide
• 英文别名: erythro-3-hydroxy-3-cyclohexyl-2,N,N-trimethylpropionamide；3-cyclohexyl-3-hydroxy-2,N,N-trimethylpropionamide；(2S,3R)-3-cyclohexyl-3-hydroxy-N,N,2-trimethylpropanamide
• CAS: 138201-37-3；138201-38-4
• 化学式: C₁₂H₂₃NO₂
• 分子量: 213.32
• InChiKey: FFLXGTSHTCTHAN-ONGXEEELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N,N-二甲基丙酰胺 在 sodium tetrahydroborate 、 Jones’ reagent 、 manganese(ll) chloride 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 0.17h， 生成 (2RS,3SR)-3-cyclohexyl-3-hydroxy-N,N,2-trimethylpropanamide
  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

• Highly Diastereoselective Synthesis of β-Hydroxy Amides from β-Keto Amides
  作者：Giuseppe Bartoli、Marcella Bosco、Enrico Marcantoni、Massimo Massaccesi、Samuele Rinaldi、Letizia Sambri

  DOI：10.1055/s-2004-829192

  日期：——

  β-Hydroxy amides with stereodefined geometry represent an important unit present in various natural products. The diastereoselective preparation of amides carrying a secondary or tertiary alcohol in β-position is described here.

  具有立体定义几何形状的 β-羟基酰胺代表存在于各种天然产物中的重要单元。此处描述了在 β 位携带仲醇或叔醇的酰胺的非对映选择性制备。
• A practical and stereoselective reduction of 3-keto-2-methyl esters or 3-keto-2-methyl amides into erythro-3-hydroxy-2-methyl esters or erythro-3-hydroxy-2-methyl amides with NaBH4 catalyzed by MnCl2
  作者：Hideaki Fujii、Koichiro Oshima、Kiitiro Utimoto

  DOI：10.1016/0040-4039(91)80775-2

  日期：1991.10

  Erythro-3-hydroxy-2-methylpropionates or erythro-3-hydroxy-2-methylpropionamides were prepared with high stereoselectivity by NaBH4 reduction of the corresponding 3-keto esters or 3-keto amides in the presence of a catalytic amount of MnCl2.

  在催化量的MnCl 2存在下，通过NaBH 4还原相应的3-酮基酯或3-酮基酰胺，以高立体选择性制备赤型-3-羟基-2-甲基丙酸酯或赤型3-羟基-2-甲基丙酰胺。。
• Crossed aldol reaction using cross-linked polymer-bound lithium dialkylamide
  作者：Atsushi Seki、Fusae Ishiwata、Youichi Takizawa、Masatoshi Asami

  DOI：10.1016/j.tet.2004.04.026

  日期：2004.5

  Cross-linked polymer-bound lithium dialkylamides were employed in crossed aldol reaction of various carbonyl compounds with aldehydes to afford the corresponding beta-hydroxycarbonyl compounds. The introduction of spacer chains to the polymer-bound lithium dialkylamide between the base moiety and the polystyrene backbone effectively enhanced yields of the desired aldol adducts. Sometimes better yields were obtained by using the polymer-bound reagent having an appropriate spacer-chain with those obtained using lithium diisopropylamide under homogeneous conditions. Repeated use of these polymeric reagents was demonstrated with no loss of efficiency. (C) 2004 Elsevier Ltd. All rights reserved.
• One-pot highly stereoselective reduction of β-keto amides to syn -γ-aminols
  作者：Giuseppe Bartoli、Marcella Bosco、Renato Dalpozzo、Enrico Marcantoni、Massimo Massaccesi、Samuele Rinaldi、Letizia Sambri

  DOI：10.1016/s0040-4039(01)01904-9

  日期：2001.12

  In the presence of titanium tetrachloride, the borane/tetrahydrofuran complex can reduce 2-methyl-3-oxoamides into the corresponding syn-aminols in good yields and high diastereoselectivity. The use of borane/dimethyl sulfide instead of BH3/THF allows a partial reduction to syn-beta -hydroxyamides. (C) 2001 Elsevier Science Ltd. All rights reserved.