4-(3-chloro-1-propynyl)-5-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-2,2-dimethyl-(4R,5S)-1,3-dioxolane | 354565-98-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(3-chloro-1-propynyl)-5-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-2,2-dimethyl-(4R,5S)-1,3-dioxolane
• 英文别名: (4R,5S)-4-(3-chloroprop-1-ynyl)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolane
• CAS: 354565-98-3
• 化学式: C₁₃H₁₉ClO₄
• 分子量: 274.744
• InChiKey: KEVWBDDJNXNSHE-MXWKQRLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3-chloro-1-propynyl)-5-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-2,2-dimethyl-(4R,5S)-1,3-dioxolane 在 咪唑 、 正丁基锂 、 lithium amide 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 正己烷 、 二氯甲烷 、 氨 、 甲苯 、 乙腈 为溶剂， 反应 40.5h， 生成 1-[1-heptyl-2,8-di(tert-butyldiphenylsilyloxy)-(1R,2R,8R)-9-decen-4,6-diynyloxymethyl]-4-methoxybenzene
  参考文献：
  名称：

  Asymmetric total syntheses of panaxytriol and panaxydol, potent antitumor agents from Panax ginseng

  摘要：

  A stereoselective syntheses of panaxytriol 1 and panaxydol 2 from D-arabinose using base induced double elimination of 4,5-O-isopropylidene propargyl chloride as a key step is described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00423-4
• 作为产物：
  描述：

  2,3-二氟-6-硝基苯胺 在 正丁基锂 、 三苯基膦 作用下， 生成 4-(3-chloro-1-propynyl)-5-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-2,2-dimethyl-(4R,5S)-1,3-dioxolane
  参考文献：
  名称：

  A highly efficient and practical method for the synthesis of chiral polyhydroxy diacetylenic alcohols

  摘要：

  An efficient protocol for the synthesis of chiral polyhydroxy diacetylenic alcohols from chiral 4,5-O-isopropylidene propargyl chlorides using strong bases is described and is useful for the synthesis of biologically active natural products. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00580-9

文献信息

• A highly efficient and practical method for the synthesis of chiral polyhydroxy diacetylenic alcohols
  作者：J.S Yadav、Arup Maiti

  DOI：10.1016/s0040-4039(01)00580-9

  日期：2001.6

  An efficient protocol for the synthesis of chiral polyhydroxy diacetylenic alcohols from chiral 4,5-O-isopropylidene propargyl chlorides using strong bases is described and is useful for the synthesis of biologically active natural products. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Asymmetric total syntheses of panaxytriol and panaxydol, potent antitumor agents from Panax ginseng
  作者：J.S Yadav、Arup Maiti

  DOI：10.1016/s0040-4020(02)00423-4

  日期：2002.6

  A stereoselective syntheses of panaxytriol 1 and panaxydol 2 from D-arabinose using base induced double elimination of 4,5-O-isopropylidene propargyl chloride as a key step is described. (C) 2002 Elsevier Science Ltd. All rights reserved.