[(Z)-6,6-dimethoxyhex-3-enyl] methanesulfonate | 220456-05-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: [(Z)-6,6-dimethoxyhex-3-enyl] methanesulfonate
• CAS: 220456-05-3
• 化学式: C₉H₁₈O₅S
• 分子量: 238.305
• InChiKey: ICPGGHXDLGAZHN-PLNGDYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(Z)-6,6-dimethoxyhex-3-enyl] methanesulfonate 在 palladium hydroxide - carbon 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 二甲基硫 、 三光气 、 盐酸羟胺 、 氨 、 水 、 氢气 、 sodium 、 三氯化铁 、 四丁基碘化铵 、 sodium hydride 、 二异丁基氢化铝 、 对甲苯磺酸 、 臭氧 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 邻二氯苯 、 乙腈 、 paraffin 、 叔丁醇 为溶剂， -78.0~325.0 ℃ 、101.33 kPa 条件下， 反应 59.5h， 生成
  参考文献：
  名称：

  Further Studies on Total Synthesis of Sarain A. Efforts Toward Annulation of the Macrocyclic Rings

  摘要：

  Studies have been conducted on testing strategies for annulation of the two macrocyclic rings onto the central tricyclic nucleus of sarain A (1). In particular, methodology has been developed for introduction into the core of C-3' and C-3 substituents, which are necessary for construction of the "eastern" and "western" macrocyclic rings of I, respectively. Formation of the western ring has been successfully addressed via a ring-closing olefin metathesis strategy utilizing the Grubbs ruthenium catalyst. With this macrocyclization approach, a key intermediate lactam has been prepared which will be utilized in a total synthesis of the natural product.

  DOI：

  10.1021/jo981821d
• 作为产物：
  描述：

  methyl (Z)-6,6-dimethoxyhex-3-enoate 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.84h， 生成 [(Z)-6,6-dimethoxyhex-3-enyl] methanesulfonate
  参考文献：
  名称：

  Further Studies on Total Synthesis of Sarain A. Efforts Toward Annulation of the Macrocyclic Rings

  摘要：

  Studies have been conducted on testing strategies for annulation of the two macrocyclic rings onto the central tricyclic nucleus of sarain A (1). In particular, methodology has been developed for introduction into the core of C-3' and C-3 substituents, which are necessary for construction of the "eastern" and "western" macrocyclic rings of I, respectively. Formation of the western ring has been successfully addressed via a ring-closing olefin metathesis strategy utilizing the Grubbs ruthenium catalyst. With this macrocyclization approach, a key intermediate lactam has been prepared which will be utilized in a total synthesis of the natural product.

  DOI：

  10.1021/jo981821d

文献信息

• Further Studies on Total Synthesis of Sarain A. Efforts Toward Annulation of the Macrocyclic Rings
  作者：Osamu Irie、Kiyohiro Samizu、James R. Henry、Steven M. Weinreb

  DOI：10.1021/jo981821d

  日期：1999.1.1

  Studies have been conducted on testing strategies for annulation of the two macrocyclic rings onto the central tricyclic nucleus of sarain A (1). In particular, methodology has been developed for introduction into the core of C-3' and C-3 substituents, which are necessary for construction of the "eastern" and "western" macrocyclic rings of I, respectively. Formation of the western ring has been successfully addressed via a ring-closing olefin metathesis strategy utilizing the Grubbs ruthenium catalyst. With this macrocyclization approach, a key intermediate lactam has been prepared which will be utilized in a total synthesis of the natural product.