(S)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)but-2-yn-1-one | 1242095-77-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)but-2-yn-1-one
• 英文别名: 1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]but-2-yn-1-one
• CAS: 1242095-77-7
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: YITWERLGGCOODL-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (S)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)but-2-yn-1-one 在 三乙烯二胺 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.33h， 生成 (1S,2E)-1-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-(pivaloyloxy)but-2-en-1-yl 2-[{(R)-3-bromo-2-methyl-5-[(triisopropylsilyl)oxy]pentan-2-yl}oxy]acetate
  参考文献：
  名称：

  Stereoselective Synthesis of the A-Ring of Armatol A from a Bromo-substituted Chiral Building Block Based on Ireland-Claisen Rearrangement and Ring-Closing Olefin Metathesis

  摘要：

  The stereoselective synthesis of the A-ring of armatol A, a natural polycyclic ether triterpene from the red alga Chondria armata, was achieved in a non-biomimetic way. The synthesis employed Ireland-Claisen rearrangement of an ester, prepared from a bromo-substituted chiral building block, for the construction of C6 and C7 stereocenters and a relay ring-closing olefin metathesis for the seven-membered ring formation.

  DOI：

  10.3987/com-14-13143
• 作为产物：
  描述：

  L-甘油醛缩丙酮 在 戴斯-马丁氧化剂 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二溴乙烷 为溶剂， 反应 4.5h， 生成 (S)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)but-2-yn-1-one
  参考文献：
  名称：

  Stereoselective Synthesis of the A-Ring of Armatol A from a Bromo-substituted Chiral Building Block Based on Ireland-Claisen Rearrangement and Ring-Closing Olefin Metathesis

  摘要：

  The stereoselective synthesis of the A-ring of armatol A, a natural polycyclic ether triterpene from the red alga Chondria armata, was achieved in a non-biomimetic way. The synthesis employed Ireland-Claisen rearrangement of an ester, prepared from a bromo-substituted chiral building block, for the construction of C6 and C7 stereocenters and a relay ring-closing olefin metathesis for the seven-membered ring formation.

  DOI：

  10.3987/com-14-13143

文献信息

• An improved synthesis of the C42–C52 segment of ciguatoxin 3C
  作者：Takafumi Saito、Kenshu Fujiwara、Yusuke Sano、Takuto Sato、Yoshihiko Kondo、Uichi Akiba、Yusuke Ishigaki、Ryo Katoono、Takanori Suzuki

  DOI：10.1016/j.tetlet.2018.02.052

  日期：2018.4

  intermediate C42–C52 (L-ring) segment was problematic. Therefore, a new and improved procedure for the C42–C52 segment, having modified protecting groups, was developed. The new route includes a chirality transferring Ireland-Claisen rearrangement for the construction of the vicinal dimethyl branching at C47–48, a one-pot cyclization process for the establishment of the stereocenters at C45 and C46 as

  在我们先前报道的构建雪茄毒素3C（CTX3C）IJKLM环的方法中，中间C42–C52（L环）链段的冗长合成过程存在问题。因此，针对C42–C52片段开发了一种经过改进的新方法，该方法具有修饰的保护基。新路线包括手性转移爱尔兰-克莱森重排，用于在C47-48处建立邻位二甲基支化；一锅环化过程，用于在C45和C46处建立立体中心，以及γ-羟基δ-内酯框架对应于L环，以及布朗的不对称巴豆基硼酸酯，用于在C43和C44处安装立体中心。新的C42–C52片段已与先前报道的C32–C41（I形环）片段成功配对，以生产IJKLM环。
• Studies toward the total synthesis of armatol F: stereoselective construction of the C6 and C7 stereocenters and formation of the A-ring skeleton
  作者：Kenshu Fujiwara、Yuta Hirose、Daisuke Sato、Hidetoshi Kawai、Takanori Suzuki

  DOI：10.1016/j.tetlet.2010.06.026

  日期：2010.8

  Armatol F, isolated from the red alga Chondria armata as a polyether triterpene, has a solitary oxepane (A-ring) and a fused tricyclic ether moiety (BCD-ring). The A-ring features a rare cis-relationship between the hydroxy group at the quaternary carbon C6 and the carbon chain at C7. As part of our program toward the total synthesis of armatol F, a new stereoselective method for the construction of

  从红藻软骨藻中分离出来的作为聚醚三萜的Armatol F具有孤立的环氧庚烷（A环）和稠合的三环醚部分（BCD环）。A环的特征是在季碳C6的羟基和C7的碳链之间罕见的顺式关系。作为我们对armatol F进行全合成的计划的一部分，基于手性传递的Ireland-Claisen重排，开发了一种用于构建C6和C7立体中心的新的立体选择性方法。还通过包括闭环烯烃复分解的方法由重排产物合成了A-环骨架。
• Stereoselective Synthesis of the A-Ring of Armatol A from a Bromo-substituted Chiral Building Block Based on Ireland-Claisen Rearrangement and Ring-Closing Olefin Metathesis
  作者：Kenshu Fujiwara、Yuta Hirose、Takafumi Saito、Ryo Katoono、Takanori Suzuki

  DOI：10.3987/com-14-13143

  日期：——

  The stereoselective synthesis of the A-ring of armatol A, a natural polycyclic ether triterpene from the red alga Chondria armata, was achieved in a non-biomimetic way. The synthesis employed Ireland-Claisen rearrangement of an ester, prepared from a bromo-substituted chiral building block, for the construction of C6 and C7 stereocenters and a relay ring-closing olefin metathesis for the seven-membered ring formation.