(NE,R,1S,2R,3S,4R)-N-benzylidene-4,7,7-trimethyl-3-phenylmethoxybicyclo[2.2.1]heptane-2-sulfinamide | 155234-15-4

• 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: (NE,R,1S,2R,3S,4R)-N-benzylidene-4,7,7-trimethyl-3-phenylmethoxybicyclo[2.2.1]heptane-2-sulfinamide
• CAS: 155234-15-4
• 化学式: C₂₄H₂₉NO₂S
• 分子量: 395.566
• InChiKey: FWYICSCGFWQFKA-QFNBXIIBSA-N

物化性质

• 沸点：
  527.4±52.0 °C(predicted)
• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  magnesium,2-methylpropane,bromide 、 (NE,R,1S,2R,3S,4R)-N-benzylidene-4,7,7-trimethyl-3-phenylmethoxybicyclo[2.2.1]heptane-2-sulfinamide 以 四氢呋喃 为溶剂， 反应 1.0h， 以50%的产率得到(R,1S,2R,3S,4R)-N-[(1S)-2,2-dimethyl-1-phenylpropyl]-4,7,7-trimethyl-3-phenylmethoxybicyclo[2.2.1]heptane-2-sulfinamide
  参考文献：
  名称：

  Application of New Camphor-Derived Mercapto Chiral Auxiliaries to the Synthesis of Optically Active Primary Amines

  摘要：

  A series of enantiomerically pure sulfinimines carrying new camphor-based mercapto chiral auxiliaries are subjected to asymmetric alkylation. Such reaction offers an excellent route to the preparation of optically active primary amines. Also reported here is an unprecedented Grignard addition of a chiral sulfenimine leading to a single enantiomer of the corresponding sulfenamide and thence produced enantiopure amine after acidic aqueous workup. The chiral auxiliary can be recovered in high yield.

  DOI：

  10.1021/jo00083a037
• 作为产物：
  描述：

  (1R,2S,3R)-3-mercapto-1,7,7-trimethylbicyclo{2.2.1}heptan-2-ol 在 N-氯代丁二酰亚胺 、 偶氮二异丁腈 、 二苯基硅烷 、 氨 、 对甲苯磺酸 、 间氯过氧苯甲酸 、 三丁基氧化锡 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 32.67h， 生成 (NE,R,1S,2R,3S,4R)-N-benzylidene-4,7,7-trimethyl-3-phenylmethoxybicyclo[2.2.1]heptane-2-sulfinamide
  参考文献：
  名称：

  Application of New Camphor-Derived Mercapto Chiral Auxiliaries to the Synthesis of Optically Active Primary Amines

  摘要：

  A series of enantiomerically pure sulfinimines carrying new camphor-based mercapto chiral auxiliaries are subjected to asymmetric alkylation. Such reaction offers an excellent route to the preparation of optically active primary amines. Also reported here is an unprecedented Grignard addition of a chiral sulfenimine leading to a single enantiomer of the corresponding sulfenamide and thence produced enantiopure amine after acidic aqueous workup. The chiral auxiliary can be recovered in high yield.

  DOI：

  10.1021/jo00083a037

文献信息

• Application of New Camphor-Derived Mercapto Chiral Auxiliaries to the Synthesis of Optically Active Primary Amines
  作者：Teng-Kuei Yang、Ruey-Yuan Chen、Dong-Sheng Lee、Wen-Shiuan Peng、Yao-Zhong Jiang、Ai-Qiao Mi、Ting-Ting Jong

  DOI：10.1021/jo00083a037

  日期：1994.2

  A series of enantiomerically pure sulfinimines carrying new camphor-based mercapto chiral auxiliaries are subjected to asymmetric alkylation. Such reaction offers an excellent route to the preparation of optically active primary amines. Also reported here is an unprecedented Grignard addition of a chiral sulfenimine leading to a single enantiomer of the corresponding sulfenamide and thence produced enantiopure amine after acidic aqueous workup. The chiral auxiliary can be recovered in high yield.