(E)-(4R)-2-benzenesulfonyl-4,6-dimethyl-non-6-en-3-one | 193416-19-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-(4R)-2-benzenesulfonyl-4,6-dimethyl-non-6-en-3-one
• 英文别名: (E,4R)-2-(benzenesulfonyl)-4,6-dimethylnon-6-en-3-one
• CAS: 193416-19-2
• 化学式: C₁₇H₂₄O₃S
• 分子量: 308.442
• InChiKey: QCRQYYDMHNQTMJ-NRJVKQNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  51.21
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-(4R)-2-benzenesulfonyl-4,6-dimethyl-non-6-en-3-one 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以89%的产率得到(E)-(4R)-4,6-dimethyl-non-6-en-3-one
  参考文献：
  名称：

  的不对称合成（ - ） - denticulatins甲乙经由一组选择性醛醇缩合内消旋二醛与手性Ñ -propionylsultam

  摘要：

  的醛醇缩合内消旋二醛3与手性获得的borylenolate Ñ -propionylsultam 4倍的产率有效地乳醇5与同时产生的5立构centers.Dithioketalization / ø -desilylation的5得到无环二醇9被转换为海洋聚丙1A和1B通过在N-丙酰基甲苯磺酰胺11的不对称烷基化和羟醛偶联10 + 15→16。

  DOI：

  10.1016/0040-4039(95)00787-d
• 作为产物：
  描述：

  (E)-1-bromo-2-methyl-2-pentene 在 六甲基磷酰三胺 、 正丁基锂 、 四甲基乙二胺 、 sodium hexamethyldisilazane 作用下， 反应 23.0h， 生成 (E)-(4R)-2-benzenesulfonyl-4,6-dimethyl-non-6-en-3-one
  参考文献：
  名称：

  Enantioselective total synthesis of (−)-denticulatins A and B using a novel group-selective aldolization of a meso dialdehyde as a key step

  摘要：

  The diastereoselective synthesis of (-)-denticulatin A (1a) was achieved for the first time in 9 steps (41% yield) based on a novel group-selective aldolization of a meso dialdehyde as a key step. The inherent chirality present in bornanesultam 4 was thus transmitted to the five stereocenters spanning C-4-C-8 in key intermediate 8. In addition, denticulatin B (1b) was obtained from the common intermediate 8 en route to denticulatin A in 10 steps and 35% overall yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00617-0

文献信息

• Asymmetric synthesis of (−)-denticulatins A and B via group-selective aldolization of a meso dialdehyde with a chiral N-propionylsultam
  作者：Wolfgang Oppolzer、Jef De Brabander、Eric Walther、Gérald Bernardinelli

  DOI：10.1016/0040-4039(95)00787-d

  日期：1995.6

  Aldolization of meso dialdehyde 3 with a borylenolate obtained from chiral N-propionylsultam 4 yields efficiently lactols 5 with simultaneous generation of five stereogenic centers.Dithioketalization/O-desilylation of 5 affords acyclic diol 9 which is converted into the marine polypropionates 1a and 1bvia the asymmetric alkylation of N-propionyltoluenesultam 11 and the aldol coupling 10 + 15 → 16.

  的醛醇缩合内消旋二醛3与手性获得的borylenolate Ñ -propionylsultam 4倍的产率有效地乳醇5与同时产生的5立构centers.Dithioketalization / ø -desilylation的5得到无环二醇9被转换为海洋聚丙1A和1B通过在N-丙酰基甲苯磺酰胺11的不对称烷基化和羟醛偶联10 + 15→16。
• Enantioselective total synthesis of (−)-denticulatins A and B using a novel group-selective aldolization of a meso dialdehyde as a key step
  作者：Jef De Brabander、Wolfgang Oppolzer

  DOI：10.1016/s0040-4020(97)00617-0

  日期：1997.7

  The diastereoselective synthesis of (-)-denticulatin A (1a) was achieved for the first time in 9 steps (41% yield) based on a novel group-selective aldolization of a meso dialdehyde as a key step. The inherent chirality present in bornanesultam 4 was thus transmitted to the five stereocenters spanning C-4-C-8 in key intermediate 8. In addition, denticulatin B (1b) was obtained from the common intermediate 8 en route to denticulatin A in 10 steps and 35% overall yield. (C) 1997 Elsevier Science Ltd.