(4R,5R)-4-ethynyl-2,2,5-trimethyl-1,3-dioxolane | 469903-96-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-4-ethynyl-2,2,5-trimethyl-1,3-dioxolane
• CAS: 469903-96-6
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: WMYINBBZTHWKOC-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R,5R)-4-ethynyl-2,2,5-trimethyl-1,3-dioxolane 在 正丁基锂 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 反应 2.0h， 生成 (S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-1-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-pent-1-yn-3-one
  参考文献：
  名称：

  Approach towards C12 oxo analogues of the side chain of pumiliotoxin B/allopumiliotoxin 339A and B

  摘要：

  A route towards the synthesis of analogues of pumiliotoxin and allopumiliotoxin side-chain is described. The C I 5,C 16 diol was introduced by asymmetric dihydroxylation using AD-mix beta of C10,C17 enynone intermediate 14, or of C13,C17 precursor 17, or by using a chiron-based route from 24. The trisubstituted alkene functionality was established using arylthio conjugate addition to ynones 16 and 27, followed by a copper-catalyzed stereoretentive reaction with methylmagnesium bromide. The approach enables access to C12 oxo systems and offers an approach towards new C14 analogues. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01071-7
• 作为产物：
  描述：

  (E)-trimethyl(pent-3-en-1-yn-1-yl)silane 在 camphor-10-sulfonic acid 、 四丁基氟化铵 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 叔丁醇 作用下， 以 丙酮 为溶剂， 反应 32.0h， 生成 (4R,5R)-4-ethynyl-2,2,5-trimethyl-1,3-dioxolane
  参考文献：
  名称：

  Approach towards C12 oxo analogues of the side chain of pumiliotoxin B/allopumiliotoxin 339A and B

  摘要：

  A route towards the synthesis of analogues of pumiliotoxin and allopumiliotoxin side-chain is described. The C I 5,C 16 diol was introduced by asymmetric dihydroxylation using AD-mix beta of C10,C17 enynone intermediate 14, or of C13,C17 precursor 17, or by using a chiron-based route from 24. The trisubstituted alkene functionality was established using arylthio conjugate addition to ynones 16 and 27, followed by a copper-catalyzed stereoretentive reaction with methylmagnesium bromide. The approach enables access to C12 oxo systems and offers an approach towards new C14 analogues. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01071-7