(3aR,6S,6aR)-6-(but-3-enyl)-2,2-dimethyldihydro-3aH-cyclopenta[d][1,3]dioxol-4(5H)-one | 1535192-86-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,6S,6aR)-6-(but-3-enyl)-2,2-dimethyldihydro-3aH-cyclopenta[d][1,3]dioxol-4(5H)-one
• 英文别名: (3aR,6S,6aR)-6-but-3-enyl-2,2-dimethyl-3a,5,6,6a-tetrahydrocyclopenta[d][1,3]dioxol-4-one
• CAS: 1535192-86-9
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: PHPSISLCYUIMOU-GDPRMGEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aR,6S,6aR)-6-(but-3-enyl)-2,2-dimethyldihydro-3aH-cyclopenta[d][1,3]dioxol-4(5H)-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以95%的产率得到(3aS,4S,6S,6aR)-6-(but-3-enyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol
  参考文献：
  名称：

  The metathesis reaction for side chain construction in carbocyclic sinefungin analogue synthesis

  摘要：

  The naturally occurring nucleoside sinefungin has found considerable use in biological investigations. More extensive sinefungin studies have been limited because few analogues have been reported due to the synthetic challenges associated with such studies. Reported herein are preparative ways to two carbocyclic sinefungin analogues: 6'-deaminocarbocyclic sinefungin and (S)-6'-hydroxy-6'-deamino-carbocyclic sinefimgin. The synthetic routes were made efficient and practical by the application of two metathesis reactions employing second generation Grubbs catalyst. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.030
• 作为产物：
  描述：

  2-环戊烯酮 、 3-Butenylmagnesium bromide 在 二甲基硫 、 六甲基磷酰三胺 、 三甲基氯硅烷 作用下， 以 四氢呋喃 为溶剂， 反应 2.83h， 以88%的产率得到(3aR,6S,6aR)-6-(but-3-enyl)-2,2-dimethyldihydro-3aH-cyclopenta[d][1,3]dioxol-4(5H)-one
  参考文献：
  名称：

  The metathesis reaction for side chain construction in carbocyclic sinefungin analogue synthesis

  摘要：

  The naturally occurring nucleoside sinefungin has found considerable use in biological investigations. More extensive sinefungin studies have been limited because few analogues have been reported due to the synthetic challenges associated with such studies. Reported herein are preparative ways to two carbocyclic sinefungin analogues: 6'-deaminocarbocyclic sinefungin and (S)-6'-hydroxy-6'-deamino-carbocyclic sinefimgin. The synthetic routes were made efficient and practical by the application of two metathesis reactions employing second generation Grubbs catalyst. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.030

文献信息

• NOVEL MONOCYCLIC AND BICYCLIC RING SYSTEM SUBSTITUTED CARBANUCLEOSIDE ANALOGUES FOR USE AS PRMT5 INHIBITORS
  申请人：Janssen Pharmaceutica NV

  公开号：US20190263833A1

  公开（公告）日：2019-08-29

  The present invention relates to novel novel monocyclic and bicyclic ring system substituted carbanucleoside analogues of Formula (I) wherein the variables have the meaning defined in the claims. The compounds according to the present invention are useful as PRMT5 inhibitors. The invention further relates to pharmaceutical compositions comprising said compounds as an active ingredient as well as the use of said compounds as a medicament.