3-((R)-4-Methyl-2-trimethylsilanyl-1-oxa-spiro[2.5]oct-4-yl)-propionitrile | 207725-74-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-((R)-4-Methyl-2-trimethylsilanyl-1-oxa-spiro[2.5]oct-4-yl)-propionitrile
• 英文别名: 3-[(4R)-4-methyl-2-trimethylsilyl-1-oxaspiro[2.5]octan-4-yl]propanenitrile
• CAS: 207725-74-4
• 化学式: C₁₄H₂₅NOSi
• 分子量: 251.444
• InChiKey: DBGHRLRJHCZGOC-ROKHWSDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-((R)-4-Methyl-2-trimethylsilanyl-1-oxa-spiro[2.5]oct-4-yl)-propionitrile 在 三氟化硼乙醚 、 氢溴酸 、 氯化铵 、 臭氧 、 锌 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 2.6h， 生成 (5aR,9aR)-3-methoxy-3,5a-dimethyl-4,5,6,7,8,9-hexahydrobenzo[c]dioxepine-9a-carbaldehyde
  参考文献：
  名称：

  Artemisinin tricyclic analogs: Role of a methyl group at C-5a

  摘要：

  New artemisinin tricyclic analogs, bearing a methyl group at C-5a were synthetized through ozonation of vinylsilanes. Presence of such a substituent was detrimental to the antimalarial activity of these trioxanes, thus reinforcing the hypothesis that tight hemin-trioxane complexes are involved in the activation phase of these compounds. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00390-6
• 作为产物：
  描述：

  3-[(1R)-2-hydroxy-2-[hydroxy(trimethylsilyl)methyl]-1-methylcyclohexyl]propanenitrile 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以75%的产率得到3-((R)-4-Methyl-2-trimethylsilanyl-1-oxa-spiro[2.5]oct-4-yl)-propionitrile
  参考文献：
  名称：

  Artemisinin tricyclic analogs: Role of a methyl group at C-5a

  摘要：

  New artemisinin tricyclic analogs, bearing a methyl group at C-5a were synthetized through ozonation of vinylsilanes. Presence of such a substituent was detrimental to the antimalarial activity of these trioxanes, thus reinforcing the hypothesis that tight hemin-trioxane complexes are involved in the activation phase of these compounds. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00390-6

文献信息

• The asymmetric Michael reaction involving chiral imines: Use of acrylonitrile as acceptor and subsequent functionalization of the adducts
  作者：Didier Desmaële、Fatima Zouhiri、Jean d'Angelo

  DOI：10.1016/0957-4166(94)80071-5

  日期：1994.9

  Condensation of chiral imines 1 and acrylonitrile led to adduct (R)-6 with an ee greater than or equal to 95 %. This adduct has then been converted into chiral synthons 9, 11, 12 and 17.