Dimethylcarbamoylmethyl-((2R,6R)-6-methyl-tetrahydro-pyran-2-yl)-carbamic acid tert-butyl ester | 689248-44-0

• 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: Dimethylcarbamoylmethyl-((2R,6R)-6-methyl-tetrahydro-pyran-2-yl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[2-(dimethylamino)-2-oxoethyl]-N-[(2R,6R)-6-methyloxan-2-yl]carbamate
• CAS: 689248-44-0
• 化学式: C₁₅H₂₈N₂O₄
• 分子量: 300.398
• InChiKey: NQSGCKGGLWYMPV-DGCLKSJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 Dimethylcarbamoylmethyl-((2R,6R)-6-methyl-tetrahydro-pyran-2-yl)-carbamic acid tert-butyl ester 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以42%的产率得到(1-Dimethylcarbamoyl-2-phenyl-ethyl)-((2R,6R)-6-methyl-tetrahydro-pyran-2-yl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  6-Methyl δ-lactol derived chiral glycine equivalents for the asymmetric synthesis of protected α-amino amides

  摘要：

  Two new delta-lactol derived chiral glycine equivalents have been prepared in one-pot processes in good yields from the known 6-methyltetrahydropyran-2-ol. Alkylation proceeds in moderate to good yields and moderate to good selectivities under experimentally simple conditions. The lactol chiral auxiliary is readily removed under mild acidic conditions to give N-Cbz protected alpha-amino amides in good yields. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.026
• 作为产物：
  描述：

  (6R)-6-methyltetrahydropyran-2-ol 以 二氯甲烷 为溶剂， 反应 40.0h， 生成 Dimethylcarbamoylmethyl-((2R,6R)-6-methyl-tetrahydro-pyran-2-yl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  6-Methyl δ-lactol derived chiral glycine equivalents for the asymmetric synthesis of protected α-amino amides

  摘要：

  Two new delta-lactol derived chiral glycine equivalents have been prepared in one-pot processes in good yields from the known 6-methyltetrahydropyran-2-ol. Alkylation proceeds in moderate to good yields and moderate to good selectivities under experimentally simple conditions. The lactol chiral auxiliary is readily removed under mild acidic conditions to give N-Cbz protected alpha-amino amides in good yields. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.026

文献信息

• 6-Methyl δ-lactol derived chiral glycine equivalents for the asymmetric synthesis of protected α-amino amides
  作者：Darren J. Dixon、Richard A.J. Horan、Nathaniel J.T. Monck

  DOI：10.1016/j.tetasy.2004.01.026

  日期：2004.3

  Two new delta-lactol derived chiral glycine equivalents have been prepared in one-pot processes in good yields from the known 6-methyltetrahydropyran-2-ol. Alkylation proceeds in moderate to good yields and moderate to good selectivities under experimentally simple conditions. The lactol chiral auxiliary is readily removed under mild acidic conditions to give N-Cbz protected alpha-amino amides in good yields. (C) 2004 Elsevier Ltd. All rights reserved.