(E)-6-((R)-4-Methyl-2-oxo-cyclohex-3-enyl)-hex-2-enoic acid methyl ester | 176980-39-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-6-((R)-4-Methyl-2-oxo-cyclohex-3-enyl)-hex-2-enoic acid methyl ester
• 英文别名: methyl (E)-6-[(1R)-4-methyl-2-oxocyclohex-3-en-1-yl]hex-2-enoate
• CAS: 176980-39-5
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: SXBJNYCDNDBZRA-HOSRBBHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-6-((R)-4-Methyl-2-oxo-cyclohex-3-enyl)-hex-2-enoic acid methyl ester 在 甲醇 、 lithium aluminium tetrahydride 、 samarium diiodide 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (1aR,3aR,7S,7aR,7bS)-7-(2-Hydroxy-ethyl)-1a-methyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7a-ol
  参考文献：
  名称：

  Asymmetric Reductive Cyclization. Total Synthesis of (−)-C₁₀-Desmethyl Arteannuin B

  摘要：

  An efficient total synthesis of (-)-C-10-desmethyl arteannuin B (5) has been achieved. The sequence features the use of a chiral auxiliary to introduce absolute asymmetry at an early stage and a stereoselective, chelation-controlled reductive cyclization of 8, using samarium diiodide as the reducing agent. The methodology promises to be applicable to the synthesis of a wide range of analogs capable of being converted to potent antimalarial agents related to artemisinin (1).

  DOI：

  10.1021/jo9600417
• 作为产物：
  描述：

  (R)-(-)-4-(4'-methyl-2'-oxocyclohex-3'-en-1'-yl)butyraldehyde dimethyl acetal 在 sodium hexamethyldisilazane 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.25h， 生成 (E)-6-((R)-4-Methyl-2-oxo-cyclohex-3-enyl)-hex-2-enoic acid methyl ester
  参考文献：
  名称：

  Asymmetric Reductive Cyclization. Total Synthesis of (−)-C₁₀-Desmethyl Arteannuin B

  摘要：

  An efficient total synthesis of (-)-C-10-desmethyl arteannuin B (5) has been achieved. The sequence features the use of a chiral auxiliary to introduce absolute asymmetry at an early stage and a stereoselective, chelation-controlled reductive cyclization of 8, using samarium diiodide as the reducing agent. The methodology promises to be applicable to the synthesis of a wide range of analogs capable of being converted to potent antimalarial agents related to artemisinin (1).

  DOI：

  10.1021/jo9600417

文献信息

• An Improved Workup for Samarium (II) Iodide Reactions
  作者：Michael K. Schwaebe、R. Daniel Little

  DOI：10.1080/00397919708004204

  日期：1997.3

  Abstract We describe a new workup for samarium (II) iodide reactions involving the use of a 10% aqueous potassium carbonate/Rochelle's salt solution. We recommend its use for a wide range of substrates, particularly those where the product is acid labile.

  摘要 我们描述了一种新的碘化钐 (II) 反应后处理，涉及使用 10% 碳酸钾水溶液/罗谢尔盐溶液。我们建议将其用于各种基材，特别是那些产品对酸不稳定的基材。
• Asymmetric Reductive Cyclization. Total Synthesis of (−)-C₁₀-Desmethyl Arteannuin B
  作者：Michael Schwaebe、R. Daniel Little

  DOI：10.1021/jo9600417

  日期：1996.1.1

  An efficient total synthesis of (-)-C-10-desmethyl arteannuin B (5) has been achieved. The sequence features the use of a chiral auxiliary to introduce absolute asymmetry at an early stage and a stereoselective, chelation-controlled reductive cyclization of 8, using samarium diiodide as the reducing agent. The methodology promises to be applicable to the synthesis of a wide range of analogs capable of being converted to potent antimalarial agents related to artemisinin (1).