(S)-(-)-N,N-dimethyl-N'-<2,(3,3-dimethyl-1-methoxybutyl)>formamidine | 138215-43-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-(-)-N,N-dimethyl-N'-<2,(3,3-dimethyl-1-methoxybutyl)>formamidine
• 英文别名: N,N-dimethyl-N'-(leucinol-methyl-ether) formamidine
• CAS: 138215-43-7
• 化学式: C₁₀H₂₂N₂O
• 分子量: 186.297
• InChiKey: UGTCNGWQUVEJCB-FJUNDMEASA-N

物化性质

• 沸点：
  227.2±42.0 °C(Predicted)
• 密度：
  0.86±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  24.83
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-(-)-N,N-dimethyl-N'-<2,(3,3-dimethyl-1-methoxybutyl)>formamidine 在 正丁基锂 作用下， 以 甲苯 为溶剂， 反应 43.33h， 生成
  参考文献：
  名称：

  Chiral formamidines. The total asymmetric synthesis of (-)-8-azaestrone and related (-)-8-aza-12-oxo-17-desoxoestrone

  摘要：

  Attachment of the chiral formamidine moiety to 6-methoxy-1,2,3,4-tetrahydroisoquinoline afforded the key chiral, nonracemic precursor 8, upon which the azasteroid skeleton was constructed. Asymmetric alkylation with alpha-halo esters or beta-halo ethers gave 15 and 22, respectively, in high ee's. Cyclization, following enamine formation with cyclopentanedione or cyclopentanone, led to the chiral steroidal skeletons 6 and 5, respectively. The final stereocenters, leading to 8-azaestrone 4 with unnatural absolute configuration (antipodal), were accomplished by intramolecular alkylation of (+)-6b and subsequent reduction and ether cleavage. For the 12-oxosteroid 3, the methyl at C-13 was inserted by initial conjupte reduction of the enone 5 with a copper hydride reagent method) requiring the presence of a silyl chloride affording 21. The addition of methyl iodide to C-13 occurred after transforming the triethylsilyl enol ether, 21, to its lithium enolate. Stereochemical assignments for both azasteroids 3 and 4 were confirmed by spectroscopic means including circular dichroism curves.

  DOI：

  10.1021/jo00043a036
• 作为产物：
  描述：

  L-叔亮氨醇 在 potassium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.33h， 生成 (S)-(-)-N,N-dimethyl-N'-<2,(3,3-dimethyl-1-methoxybutyl)>formamidine
  参考文献：
  名称：

  Chiral formamidines. The total asymmetric synthesis of (-)-8-azaestrone and related (-)-8-aza-12-oxo-17-desoxoestrone

  摘要：

  Attachment of the chiral formamidine moiety to 6-methoxy-1,2,3,4-tetrahydroisoquinoline afforded the key chiral, nonracemic precursor 8, upon which the azasteroid skeleton was constructed. Asymmetric alkylation with alpha-halo esters or beta-halo ethers gave 15 and 22, respectively, in high ee's. Cyclization, following enamine formation with cyclopentanedione or cyclopentanone, led to the chiral steroidal skeletons 6 and 5, respectively. The final stereocenters, leading to 8-azaestrone 4 with unnatural absolute configuration (antipodal), were accomplished by intramolecular alkylation of (+)-6b and subsequent reduction and ether cleavage. For the 12-oxosteroid 3, the methyl at C-13 was inserted by initial conjupte reduction of the enone 5 with a copper hydride reagent method) requiring the presence of a silyl chloride affording 21. The addition of methyl iodide to C-13 occurred after transforming the triethylsilyl enol ether, 21, to its lithium enolate. Stereochemical assignments for both azasteroids 3 and 4 were confirmed by spectroscopic means including circular dichroism curves.

  DOI：

  10.1021/jo00043a036

文献信息

• The asymmetric synthesis of 1-alkyl-2,3,4,5-tetrahydro-benzazepines and benzo[β]-1-azabicyclo[5,3,1]decanes
  作者：A.I Meyers、Richard H Hutchings

  DOI：10.1016/s0040-4020(01)80537-8

  日期：1993.2

  The metalation-alkylation of benzazepine formamidines gives high yields and good diastereoselectivity of 1-substituted derivatives. Removal of the chiral auxiliary leads to the title compounds in 84-96% ee and represents the first chiral benzazepines prepared via asymmetric synthesis.
• C2 symmetric amines. III. An asymmetric synthesis of (S,S)-1,3-dialkyl lsoindolines by sequential formamidine alkylation
  作者：A.I Meyers、Braulio Santiago

  DOI：10.1016/0040-4039(95)01182-h

  日期：1995.8