(3aS,6R,7aR)-hexahydro-1-<(ζ)-(hydroxy)(methoxy)acetyl>-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazole 2,2-dioxide | 196933-71-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3aS,6R,7aR)-hexahydro-1-<(ζ)-(hydroxy)(methoxy)acetyl>-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazole 2,2-dioxide
• 英文别名: N-glyoxyloyl-(2R)-bornane-10,2-sultam methyl hemiacetal；(2R)-N-glyoxyloylbornane-10,2-sultam；(3aS,6R,7aR)-hexahydro-1-[(ζ)-(hydroxy)(methoxy)acetyl]-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazole 2,2-dioxide；1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-2-hydroxy-2-methoxyethanone；1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-2-hydroxy-2-methoxyethanone
• CAS: 196933-71-8
• 化学式: C₁₃H₂₁NO₅S
• 分子量: 303.379
• InChiKey: JTMSVAFVXBFFIR-AAUWTOINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aS,6R,7aR)-hexahydro-1-<(ζ)-(hydroxy)(methoxy)acetyl>-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazole 2,2-dioxide 110.0 ℃ 、13.33 Pa 条件下， 反应 2.0h， 生成 (2R)-N-glyoxylbornane-10,2-sultam
  参考文献：
  名称：

  不对称[4 + 2]的环戊二烯环加成到Ñ '-tosylimine的ñ -glyoxyloyl-（2 - [R）-bornane-10,2-磺内酰胺

  摘要：

  描述了使用改良的福尔摩斯方法首次合成N-乙二酰氯（-2 R）-降冰片烷10,2-磺胺的N'-甲苯胺。所述Ñ '-tosylimine被用作与环戊二烯的路易斯酸催化的非对映选择性亚氨基Diels-Alder反应亲双烯体，得到具有良好的非对映异构过量cycloadducts。不对称感应的方向取决于所用的路易斯酸。

  DOI：

  10.1016/s0957-4166(97)00305-4
• 作为产物：
  描述：

  (1S)-N-crotyl-2,10-camphorsultam 以90%的产率得到
  参考文献：
  名称：

  Freund Ralf, Allagiannis Christos, Schoenholzer Peter, Bernauer Karl, Helv. chim. acta, 77 (1994) N 3, S 615-621

  摘要：

  DOI：

文献信息

• Derivatives of (2<i>R</i>)-<i>N</i>-Glyoxylbornane-10,2-sultam and Their Use as auxiliaries in the diastereoselective spirocyclization of 2-substituted tryptamines
  作者：Ralf Freund、Christos Allagiannis、Peter Schönholzer、Karl Bernauer

  DOI：10.1002/hlca.19940770304

  日期：1994.5.11

  prepared from crotonamide 5 (Scheme 2). Particularly hemiacetal 7, but also 6 and the ‘dimer’ 8 (obtained from 7) may serve as homochiral auxiliaries. The structure of 8 was determined by X-ray analysis. By arenesulfonyl halides, tryptimines 12–14 of 4 were diastereoselectively transformed into spirotricycles 15–17 and 19.

  由巴豆酰胺5（方案2）制备乙醛酰胺4的粗水合物6和结晶半缩醛7。特别是半缩醛7，但也可以是6和'二聚体' 8（由7获得）可以用作同手性助剂。通过X射线分析确定8的结构。由芳烃磺酰基卤化物，tryptimines 12-14的4进行非对映选择性转化为spirotricycles 15-17和19。
• Highly stereoselective addition of 2-trimethylsilyloxyfuran to N-glyoxyloyl-(2R)-bornane-10,2-sultam
  作者：Tomasz Bauer

  DOI：10.1016/0957-4166(96)00097-3

  日期：1996.4

  Eu(fod)3-catalyzed stereoselective nucleophilic addition of 2-trimethylsilyloxyfuran to N-glyoxyloyl-(2R)-bornane-10,2-sultam yields g-substituted butenolides with high diastereoselectivity.

  Eu（fod）3催化的2-三甲基甲硅烷基氧基呋喃向N-乙氧基乙酰基-（2 R）-降冰片烷10,2-sultam的立体选择性亲核加成反应生成高非对映选择性的g-取代丁烯内酯。
• Pictet-Spengler Reaction of Biogenic Amines with (2R)-N-Glyoxyloylbornane-10,2-sultam. Enantioselective Synthesis of (S)-(+)-N-Methylcalycotomine and (R)-(+)-Xylopinine
  作者：Zbigniew Czarnocki、Zbigniew Arazny

  DOI：10.3987/com-99-8681

  日期：——

  The Pictet-Spengler reaction of (2R)-N-glyoxyloylbornane-10,2-sultam with dopamine hydrochloride gave the condensation product, which was further converted into (S)-(+)-N)-methylcalycotomine and (R)-(+)-xylopinine of high enantiomeric purity.
• Lee, Jung Gyu; Choi, Kyung Il; Pae, Ae Nim, Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, # 10, p. 1314 - 1317
  作者：Lee, Jung Gyu、Choi, Kyung Il、Pae, Ae Nim、Koh, Hun Yeong、Kang, Yonghan、Cho, Yong Seo

  DOI：——

  日期：——
• Asymmetric [4+2] cycloaddition of cyclopentadiene to N′-tosylimine of N-glyoxyloyl-(2R)-bornane-10,2-sultam
  作者：Tomasz Bauer、Sławomir Szymański、Artur Jeżewski、Przemysław Gluziński、Janusz Jurczak

  DOI：10.1016/s0957-4166(97)00305-4

  日期：1997.8

  The first synthesis of the N′-tosylimine of N-glyoxyloyl-(2R)-bornane-10,2-sultam using a modified Holmes method is described. The N′-tosylimine was used as a dienophile in the Lewis acid-catalyzed diastereoselective imino-Diels-Alder reaction with cyclopentadiene to give cycloadducts with good diastereoisomeric excess. The direction of the asymmetric induction depends on the Lewis acid used.

  描述了使用改良的福尔摩斯方法首次合成N-乙二酰氯（-2 R）-降冰片烷10,2-磺胺的N'-甲苯胺。所述Ñ '-tosylimine被用作与环戊二烯的路易斯酸催化的非对映选择性亚氨基Diels-Alder反应亲双烯体，得到具有良好的非对映异构过量cycloadducts。不对称感应的方向取决于所用的路易斯酸。