methyl (1S,2R)-1-benzamido-2-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>cyclopropanecarboxylate | 154799-43-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (1S,2R)-1-benzamido-2-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>cyclopropanecarboxylate
• 英文别名: methyl (1S,2R)-1-benzamido-2<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>cyclopropanecarboxylate；methyl (1S,2R) 2<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>-1-benzamidocyclopropancarboxylate；(1S,2R)-methyl-1-benzamido-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclopropanecarboxylate；methyl (1S,2R) 2((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-benzamidocyclopropancarboxylate；methyl (1S,2R)-1-benzamido-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclopropane-1-carboxylate
• CAS: 154799-43-6
• 化学式: C₁₇H₂₁NO₅
• 分子量: 319.357
• InChiKey: FHGROLJSRUCECW-AHIWAGSCSA-N

物化性质

• 沸点：
  476.1±45.0 °C(predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (1S,2R)-1-benzamido-2-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>cyclopropanecarboxylate 在 盐酸 、 四氯化碳 、 sodium hydroxide 、 sodium tetrahydroborate 、 sodium periodate 、 三苯基膦 、 methyloxirane 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 为溶剂， 反应 93.0h， 生成 (1S,2R)-allonorcoronamic acid
  参考文献：
  名称：

  A straightforward synthesis of (−)-(1S,2R)-Allonorcoronamic acid using D-mannitol as the chiral source

  摘要：

  （−)-(1S,2R)-异冠型RNA烷酸以对映体纯净形式合成，源自甲基 (1S,2R)-1-苯酰胺-2-[(S)-2,2-二甲基-1,3-二氧戊环-4-基]环丙烷羧酸酯，该化合物通过手性氮杂环酮上进行甲基插入法，手性氮杂环酮由1,2-O-异丙叉-D-甘露糖醛酸衍生而来。

  DOI：

  10.1016/0957-4166(95)00269-u
• 作为产物：
  描述：

  Z-2-phenyl-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylen>-5(4H)-oxazolone 在 sodium methylate 、 sodium hydride 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 methyl (1S,2R)-1-benzamido-2-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>cyclopropanecarboxylate
  参考文献：
  名称：

  手性恶唑酮与氧代砜亚砜环丙烷化反应的研究

  摘要：

  研究了由1,2-O-异亚丙基-D-甘油醛衍生的手性Z-恶唑酮对作为环丙烷化剂的亚砜基phon的行为。描述了产物比例对溶剂和温度的依赖性。

  DOI：

  10.1016/0040-4020(95)00033-5

文献信息

• Study of the reaction of a chiral oxazolone with oxosulphonium methylides as cyclopropanating agents
  作者：Carlos Cativiela、María D. Díaz-de-Villegas、Ana I. Jiménez

  DOI：10.1016/0040-4020(95)00033-5

  日期：1995.3

  The behaviour of the chiral Z-oxazolone derived from 1,2-O-isopropylidene-D-glyceraldehyde towards oxosulphonium methylides as cyclopropanating agents has been studied. The solvent and temperature dependence of the ratio of the products is described.

  研究了由1,2-O-异亚丙基-D-甘油醛衍生的手性Z-恶唑酮对作为环丙烷化剂的亚砜基phon的行为。描述了产物比例对溶剂和温度的依赖性。
• A simple synthesis of (−)-(1S,2R)-allocoronamic acid in its enantiomerically pure form
  作者：Carlos Cativiela、María D. Díaz-de-Villegas、Ana I. Jiménez

  DOI：10.1016/0957-4166(94)00373-j

  日期：1995.1

  (−)-(1S,2R)-Allocoronamic acid was synthesized in its enantiomerically pure form by starting from the chiral azlactone derived from 1,2-O-isopropylidene-D-glyceraldehyde in an overall yield of 37 %.

  通过从衍生自1,2-O-异亚丙基-D-甘油醛的手性氮杂内酯为原料，以对映体纯的形式合成（-）-（1S，2R）-别香醛酸，总产率为37％。
• 1,3-Dipolar cycloaddition of diazomethane with a chiral azlactone
  作者：Carlos Cativiela、María D Díaz-de-Villegas、Ana I Jiménez、Fernando Lahoz

  DOI：10.1016/s0040-4039(00)75853-9

  日期：1994.1

  The chiral Z-azlactone derived from 1,2-O-isopropylidene-D-glyceraldehyde reacted with diazomethane to afford stereoselectively and diastereoselectively a cis spiro-azlactone. Solvent and temperature dependence of the ratio of the products is described
• Atmospheric pressure chemical ionization multi-stage mass spectrometry in the characterization of stereoisomeric synthons of cyclopropane amino acids
  作者：Simone Cristoni、Carlos Cativiela、Ana I. Jim�nez、Pietro Traldi

  DOI：10.1002/(sici)1096-9888(200002)35:2<199::aid-jms930>3.0.co;2-6

  日期：2000.2

  The mass spectrometric behaviour of (1S,2R)-, (1R,2R)-, (1R,2S)- and (1S,2S)-2-[(S)-2,2-dimethyl-1, 3-dioxolan-4-yl]-1-spiro-¿4'[2'-phenyl-5'(4'H)-oxazolone]¿ cyclopropane (2) and (1S,2R)-, (1R,2R)-, (1R,2S)- and (1S, 2S)-methyl-1-benzamido-2-[(S)-2,2-dimethyl-1, 3-dioxolan-4-yl]cyclopropanecarboxylate (3) was studied under atmospheric pressure ionization conditions and by multi-stage mass spectrometric (MS(n)) experiments performed with an ion trap. Interestingly, by using methanol as solvent, compounds 2 lead to [M + H + CH(3)OH](+) ions which, as proved by collisional experiments, exhibit the same structure of the corresponding compound 3. MS/MS of [MH](+) ions allows a clear characterization of the different stereoisomers, which give rise to specific fragmentation pathways, rationalized with respect to the structure of the neutral molecules.
• A straightforward synthesis of (−)-(1S,2R)-Allonorcoronamic acid using D-mannitol as the chiral source
  作者：Carlos Cativiela、María D. Díaz-de-Villegas、Ana I. Jiménez

  DOI：10.1016/0957-4166(95)00269-u

  日期：1995.8

  (-)-(1S,2R)-Allonorcoronamic acid was synthesized in its enantiomerically pure form from methyl (1S,2R)-1-benzamido-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclopropanecarboxylate, which is easily obtained by methylene insertion on the chiral azlactone derived from 1,2-O-isopropylidene-D-glyceraldehyde.

  （−)-(1S,2R)-异冠型RNA烷酸以对映体纯净形式合成，源自甲基 (1S,2R)-1-苯酰胺-2-[(S)-2,2-二甲基-1,3-二氧戊环-4-基]环丙烷羧酸酯，该化合物通过手性氮杂环酮上进行甲基插入法，手性氮杂环酮由1,2-O-异丙叉-D-甘露糖醛酸衍生而来。