(2S,3R)-2-hydroxy-3-(methoxymethyl)-N,3-dimethylpentanamide | 402913-55-7

• 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: (2S,3R)-2-hydroxy-3-(methoxymethyl)-N,3-dimethylpentanamide
• CAS: 402913-55-7
• 化学式: C₉H₁₉NO₃
• 分子量: 189.255
• InChiKey: LFAZRZMGPJXAJE-VXNVDRBHSA-N

物化性质

• 沸点：
  371.1±32.0 °C(Predicted)
• 密度：
  1.010±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-hydroxy-3-(methoxymethyl)-N,3-dimethylpentanamide 在 三溴化硼 、 水 、 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (3S,4R)-4-ethyl-3-hydroxy-4-methyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Enantioselective synthesis of β,β-dialkyl α-hydroxy γ-butyrolactones

  摘要：

  An ephedrine-derived morpholine dione is employed in the synthesis of chiral alkylidene morpholinones that are efficiently converted to beta -substituted alpha-gamma -dihydroxy butyramides, precursors of the corresponding butyrolactones. Enantioselective synthesis of a spiro analog of pantolactone as well as a naturally occurring pantolactone homolog is achieved with this protocol. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01979-7
• 作为产物：
  描述：

  (2,1')Z,5S,6R-4,5-dimethyl-2-(1-methylpropylidene)-6-phenylmorpholin-3-one 在 三乙基硅烷 、 硫酸 、 氨 、 sodium 、 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 0.03h， 生成 (2S,3R)-2-hydroxy-3-(methoxymethyl)-N,3-dimethylpentanamide
  参考文献：
  名称：

  Enantioselective synthesis of β,β-dialkyl α-hydroxy γ-butyrolactones

  摘要：

  An ephedrine-derived morpholine dione is employed in the synthesis of chiral alkylidene morpholinones that are efficiently converted to beta -substituted alpha-gamma -dihydroxy butyramides, precursors of the corresponding butyrolactones. Enantioselective synthesis of a spiro analog of pantolactone as well as a naturally occurring pantolactone homolog is achieved with this protocol. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01979-7

文献信息

• Enantioselective synthesis of β,β-dialkyl α-hydroxy γ-butyrolactones
  作者：Sunil V Pansare、Annyt Bhattacharyya

  DOI：10.1016/s0040-4039(01)01979-7

  日期：2001.12

  An ephedrine-derived morpholine dione is employed in the synthesis of chiral alkylidene morpholinones that are efficiently converted to beta -substituted alpha-gamma -dihydroxy butyramides, precursors of the corresponding butyrolactones. Enantioselective synthesis of a spiro analog of pantolactone as well as a naturally occurring pantolactone homolog is achieved with this protocol. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Enantioselective synthesis of pantolactone analogues from an ephedrine-derived morpholine-dione
  作者：Sunil V Pansare、Annyt Bhattacharyya

  DOI：10.1016/s0040-4020(03)00408-3

  日期：2003.4

  An efficient enantioselective synthesis of beta,beta-dialkyl alpha-hydroxy gamma-butyrolactones, analogues of pantolactone, has been developed employing a stereoselective Prins reaction of chiral alkylidene morpholinones, as the key step. Enantioselective synthesis of a naturally occurring pantolactone homologue and a spiro analogue of pantolactone was achieved with this protocol. (C) 2003 Elsevier Science Ltd. All rights reserved.