(4R,5S,6S,7R)-hexahydro-5,6-isopropylidenedioxy-4,7-bis(phenylmethyl)-2H-diazapin-2-one | 180302-24-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂卓
• 英文名称: (4R,5S,6S,7R)-hexahydro-5,6-isopropylidenedioxy-4,7-bis(phenylmethyl)-2H-diazapin-2-one
• 英文别名: (3aS,4R,8R,8aS)-4,5,7,8-tetrabenzyl-2,2-dimethyl-3a,4,8,8a-tetrahydro-[1,3]dioxolo[4,5-e][1,3]diazepin-6-one
• CAS: 180302-24-3
• 化学式: C₃₆H₃₈N₂O₃
• 分子量: 546.709
• InChiKey: NQLONDGQLMIJHU-WZJLIZBTSA-N

物化性质

• 熔点：
  126-129 °C
• 沸点：
  694.3±55.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,5S,6S,7R)-hexahydro-5,6-isopropylidenedioxy-4,7-bis(phenylmethyl)-2H-diazapin-2-one 在 potassium tert-butylate 、 sodium 作用下， 以 四氢呋喃 、 氨 为溶剂， 生成 (3aS,4R,8R,8aS)-5-Allyl-4,7,8-tribenzyl-2,2-dimethyl-hexahydro-1,3-dioxa-5,7-diaza-azulen-6-one
  参考文献：
  名称：

  一类新型的HIV蛋白酶抑制剂非对称环状脲二醇的合成

  摘要：

  通式1的不对称环状脲二醇可以通过衍生自对称二胺2的异脲或通过使用溶解性金属还原从某些对称环状脲8中选择性地除去苄基来制备。

  DOI：

  10.1016/s0040-4039(98)01263-5
• 作为产物：
  描述：

  (1R,1'R)-1,1'-((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(2-phenylethanamine) 在 potassium tert-butylate 、 己酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (4R,5S,6S,7R)-hexahydro-5,6-isopropylidenedioxy-4,7-bis(phenylmethyl)-2H-diazapin-2-one
  参考文献：
  名称：

  一类新型的HIV蛋白酶抑制剂非对称环状脲二醇的合成

  摘要：

  通式1的不对称环状脲二醇可以通过衍生自对称二胺2的异脲或通过使用溶解性金属还原从某些对称环状脲8中选择性地除去苄基来制备。

  DOI：

  10.1016/s0040-4039(98)01263-5

文献信息

• Grignard Addition to Aldonitrones. Stereochemical Aspects and Application to the Synthesis of C₂-Symmetric Diamino Alcohols and Diamino Diols
  作者：Alessandro Dondoni、Daniela Perrone、Marilisa Rinaldi

  DOI：10.1021/jo980980u

  日期：1998.12.1

  A new example of the stereoselective installation of the amino group at a saturated carbon center via organometallic addition of chiral aldehydes to nitrones is illustrated by the synthesis of 1,3-diamino propanol 1 and 1,4-diamino butandiol 2 units. Three diamino alcohol 1 stereotriads were obtained by stereoselective addition of alkylmagnesium halides (benzyl, cyclohexylmethyl, and metallyl) to the N-benzyl nitrones derived from beta-amino-alpha-hydroxy aldehydes followed by reduction of the resulting N-benzylhydroxylamines. Three 1,4-dibenzyl substituted stereoisomers of type 2 with fixed S configuration at C2 and C3 were prepared by sequential and simultaneous amination in two directions starting from L-threose nitrone and L-tartraldehyde bis-nitrone, respectively. The R,S,S,R isomer obtained by the former route was converted into a seven-membered ring cyclic urea (1,3-diazapin-2-one), i.e., a compound that belongs to a class of nonpeptide HIV-1 protease inhibitors.
• Synthesis of unsymmetric cyclic urea diols, a novel class of HIV protease inhibitors
  作者：Benjamin R.P. Stone、Gregory D. Harris、Reginald O. Cann、Thomas E. Smyser、Pat N. Confalone

  DOI：10.1016/s0040-4039(98)01263-5

  日期：1998.8

  Unsymmetric cyclic urea diols of general structure 1 can be prepared either via an isourea derived from the symmetric diamine 2 or by the selective removal of a benzyl group from certain symmetric cyclic ureas 8, employing dissolving metal reduction.

  通式1的不对称环状脲二醇可以通过衍生自对称二胺2的异脲或通过使用溶解性金属还原从某些对称环状脲8中选择性地除去苄基来制备。