(1R,2S,3R,4S)-3-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>-bicyclo<2.2.1>-hept-5-en-2-spiro<4'<2'-phenyl-5'(4'H)-oxazolone>> | 155932-76-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,2S,3R,4S)-3-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>-bicyclo<2.2.1>-hept-5-en-2-spiro<4'<2'-phenyl-5'(4'H)-oxazolone>>
• 英文别名: (1R,2S,3R,4S)-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>-bicyclo<2.2.1>hept-5-en-2-spiro-<4'-<2'-phenyl-5'(4'H)-oxazolone>>；(1R,2S,3R,4S)-3-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>bicyclo<2.2.1>hept-5-en-2-spiro-<4'<2'-phenyl-5'(4'H)-oxazolone>>；(1R,2S,3R,4S)-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-bicyclo[2.2.1]hept-5-en-2-spiro-[4'-(2'-phenyl-5'(4'H)-oxazolone)]；(1'S,4S,4'R,6'R)-6'-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylspiro[1,3-oxazole-4,5'-bicyclo[2.2.1]hept-2-ene]-5-one
• CAS: 155932-76-6
• 化学式: C₂₀H₂₁NO₄
• 分子量: 339.391
• InChiKey: QWCAGRGKZSOAGK-YXTCSXCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2S,3R,4S)-3-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>-bicyclo<2.2.1>-hept-5-en-2-spiro<4'<2'-phenyl-5'(4'H)-oxazolone>> 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 28.5h， 生成 methyl (1S,2S,3R,4R)-2-benzamido-3-(1,2-dihydroxyethyl)bicyclo[2.2.1]heptane-2-carboxylate
  参考文献：
  名称：

  Diastereoselective synthesis of (1S,2S,3R,4R) and (1R,2S,3R,4S)-bicyclo[2.2.1]hept-2-amino-2,3-dicarboxylic acids: New conformationally-constrained (S)-aspartic acid analogues

  摘要：

  The title compounds were prepared from key intermediates readily obtained by the stereoselective Diels-Alder reaction of (Z)-2-phenyl-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylene]-5(4H)-oxazolone, a chiral az-lactone derived from (R)-glyceraldehyde and cyclopentadiene. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00172-3
• 作为产物：
  描述：

  环戊二烯 、 Z-2-phenyl-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylen>-5(4H)-oxazolone 以 二氯甲烷 为溶剂， 反应 96.0h， 生成 (1S,2S,3R,4R)-3-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>-bicyclo<2.2.1>-hept-5-en-2-spiro<4'<2'-phenyl-5'(4'H)-oxazolone>> 、 (1R,2S,3R,4S)-3-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>-bicyclo<2.2.1>-hept-5-en-2-spiro<4'<2'-phenyl-5'(4'H)-oxazolone>>
  参考文献：
  名称：

  Asymmetric Diels-Alder reaction of a chiral azlactone

  摘要：

  The chilal Z-azlactone derived from 1,2-O-isopropylidene-D-glyceraldehyde underwent facial diastereoselective Diels-Alder reaction with cyclopentadiene. Catalyst and temperature dependence of the product ratio is described The absolute configuration of the major compound was established by an X-ray crystallographic analysis.

  DOI：

  10.1016/s0957-4166(00)86161-3

文献信息

• Diels-Alder reactions of (E)-2-phenyl-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylen]-5(4H)-oxazolone with heterogeneous catalysts
  作者：Carlos Cativiela、JoséM Fraile、JoséI García、Ma Pilar López、JoséA Mayoral、Elisabet Pires

  DOI：10.1016/0957-4166(96)00295-9

  日期：1996.8

  Diels-Alder reactions of (E)-2-Phenyl-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylen]-5(4H)-oxazolone with 2,3-dimethylbutadiene, cyclopentadiene, and 2-methyl-1,3-butadiene (isoprene) are catalysed by silica gel and aluminium, titanium, and zinc catalyst supported on silica gel. Overall conversion and asymmetric induction are obtained with very low percentages of E/Z isomerisation. The best results are obtained with ZnCl2 supported on silica gel, and by carrying out the reaction without a solvent. The stereochemistry of the major cycloadducts has been determined by single crystal X-ray structure determination and AM1 calculations of the corresponding transition structures. Copyright (C) 1996 Elsevier Science Ltd
• Study of the asymmetric diels-alder reaction of a chiral azlactone
  作者：Elena Buñuel、Carlos Cativiela、Maria D. Diaz-de-Villegas、José I. Garcia

  DOI：10.1016/0957-4166(94)80040-5

  日期：1994.4

  The chiral Z-azlactone derived from 1,2-O-isopropylidene-D-glyceraldehyde underwent diastereoselective Diels-Alder reaction with cyclopentadiene. Catalyst, temperature and solvent dependence of the product ratio is described.
• Diastereoselective synthesis of (1S,2S,3R,4R) and (1R,2S,3R,4S)-bicyclo[2.2.1]hept-2-amino-2,3-dicarboxylic acids: New conformationally-constrained (S)-aspartic acid analogues
  作者：Elena Buñuel、Carlos Cativiela、Maria D. Diaz-de-Villegas

  DOI：10.1016/0957-4166(96)00172-3

  日期：1996.5

  The title compounds were prepared from key intermediates readily obtained by the stereoselective Diels-Alder reaction of (Z)-2-phenyl-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylene]-5(4H)-oxazolone, a chiral az-lactone derived from (R)-glyceraldehyde and cyclopentadiene. Copyright (C) 1996 Elsevier Science Ltd
• Asymmetric Diels-Alder reaction of a chiral azlactone
  作者：Elena Buñuel、Carlos Cativiela、Maria D. Diaz-de-Villegas

  DOI：10.1016/s0957-4166(00)86161-3

  日期：1994.1

  The chilal Z-azlactone derived from 1,2-O-isopropylidene-D-glyceraldehyde underwent facial diastereoselective Diels-Alder reaction with cyclopentadiene. Catalyst and temperature dependence of the product ratio is described The absolute configuration of the major compound was established by an X-ray crystallographic analysis.