| 170877-44-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 170877-44-8
• 化学式: C₂₂H₂₇NO₅
• 分子量: 385.46
• InChiKey: SOHHNUUOBBMKHH-VBGUPWIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  73.86
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  A New Conformationally Restricted Aspartic Acid Analogue with a Bicyclo[2.2.2]octane Skeleton

  摘要：

  The bicyclo[2.2.2]octane cage in (2R,3S)-3-benzamido-3-methoxycarbonylbicyclo [2.2.2] octane-2-carboxylic acid, C18H21NO5, has approximate D-3 symmetry and the three six-membered rings of this fragment all deviate slightly from ideal boat conformations. The values determined for the torsion angles about the N-C alpha (psi) and C alpha-CO (psi) bonds correspond to a semi-extended conformation for the amino acid residue, The crystal structure is stabilized by two intermolecular hydrogen bonds (O-H .. O and N-H ... O) involving the carboxylic acid, the benzamido and the methyl ester groups.

  DOI：

  10.1107/s0108270196004696
• 作为产物：
  描述：

  sodium methylate 、 (1R,2S,3R,4S)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-bicyclo[2.2.2]-oct-5-en-2-spiro(4'(2'-phenyl-5'(4'H)-oxazolone)) 以 甲醇 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  A New Conformationally Restricted Aspartic Acid Analogue with a Bicyclo[2.2.2]octane Skeleton

  摘要：

  The bicyclo[2.2.2]octane cage in (2R,3S)-3-benzamido-3-methoxycarbonylbicyclo [2.2.2] octane-2-carboxylic acid, C18H21NO5, has approximate D-3 symmetry and the three six-membered rings of this fragment all deviate slightly from ideal boat conformations. The values determined for the torsion angles about the N-C alpha (psi) and C alpha-CO (psi) bonds correspond to a semi-extended conformation for the amino acid residue, The crystal structure is stabilized by two intermolecular hydrogen bonds (O-H .. O and N-H ... O) involving the carboxylic acid, the benzamido and the methyl ester groups.

  DOI：

  10.1107/s0108270196004696

文献信息

• Z -2-Phenyl-4-[(S)- 2,2-dimethyl-1,3-dioxolan-4-ylmethylen]-5(4H)-oxazolone as the Dienophile in Asymmetric Diels-Alder Reactions
  作者：Elena Buñuel、Carlos Cativiela、Maria D. Diaz-de-Villegas

  DOI：10.1016/0040-4020(95)00501-x

  日期：1995.8

  Diels-Alder reactions of Z-2-phenyl-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylen]-5(4H)-oxazolone and several cyclic and open chain dienes are studied. Less-reactive dienes required longer reaction times and led to isomerization of the Z-oxazolone and isolation of products derived from the E-isomer; Lewis acid catalysts were used to shorten the reaction times. In all cases high diastereofacial selectivity

  研究了Z-2-苯基-4-[（S）-2,2-二甲基-1,3-二氧戊环-4-基亚甲基] -5（4H）-恶唑酮与几种环状和开链二烯的Diels-Alder反应。反应性较低的二烯需要更长的反应时间，并导致Z-恶唑酮的异构化和E异构体衍生产物的分离；使用路易斯酸催化剂来缩短反应时间。在所有情况下，均观察到高非对映体选择性，并且可以以高光学纯度获得Diels-Alder加合物。加合物的立体化学已通过单晶X射线结构测定，1 H-NMR分析和机理考虑得到阐明。