(4R,5R)-5-(hept-6-enoyl)-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide | 1446403-76-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-5-(hept-6-enoyl)-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide
• 英文别名: (4R,5R)-5-hept-6-enoyl-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide
• CAS: 1446403-76-4
• 化学式: C₁₅H₂₅NO₄
• 分子量: 283.368
• InChiKey: UOWQBIAUAMGTSH-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5R)-5-(hept-6-enoyl)-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide 在 cerium(III) chloride heptahydrate 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以94%的产率得到(4R,5S)-5-((R)-1-hydroxyhept-6-en-1-yl)-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide
  参考文献：
  名称：

  Enantiospecific formal total synthesis of (+)-aspicilin

  摘要：

  An enantiospecific formal total synthesis of the macrolide (+)-aspicilin is accomplished from chiral pool tartaric acid. Key features of the synthesis include desymmetrization of the bis-dimethyl amide of tartaric acid and further elaboration to the title compound using olefin cross-metathesis and Yamaguchi macrolactonization as the pivotal steps. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.041
• 作为产物：
  描述：

  magnesium,hex-1-ene,bromide 、 (4R,5R)-4,5-二(二甲氨基羰基)-2,2-二甲基二氧 以 四氢呋喃 为溶剂， 以82%的产率得到(4R,5R)-5-(hept-6-enoyl)-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide
  参考文献：
  名称：

  Enantiospecific formal total synthesis of (+)-aspicilin

  摘要：

  An enantiospecific formal total synthesis of the macrolide (+)-aspicilin is accomplished from chiral pool tartaric acid. Key features of the synthesis include desymmetrization of the bis-dimethyl amide of tartaric acid and further elaboration to the title compound using olefin cross-metathesis and Yamaguchi macrolactonization as the pivotal steps. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.041

文献信息

• Enantiospecific formal total synthesis of (+)-aspicilin
  作者：Vasudeva Rao Gandi

  DOI：10.1016/j.tet.2013.05.041

  日期：2013.8

  An enantiospecific formal total synthesis of the macrolide (+)-aspicilin is accomplished from chiral pool tartaric acid. Key features of the synthesis include desymmetrization of the bis-dimethyl amide of tartaric acid and further elaboration to the title compound using olefin cross-metathesis and Yamaguchi macrolactonization as the pivotal steps. (C) 2013 Elsevier Ltd. All rights reserved.