(2S,5S)-2,5-diphenyl-1,3-dioxolan-4-one | 90581-53-6

• 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: (2S,5S)-2,5-diphenyl-1,3-dioxolan-4-one
• 英文别名: trans-2,5-diphenyl-1,3-dioxolan-4-one；2,5-diphenyl-1,3-dioxolan-4-one；(2R,5S)-2,5-diphenyl-1,3-dioxolan-4-one
• CAS: 90581-53-6
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: ZETHIMXJYSHLHZ-DZGCQCFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,5S)-2,5-diphenyl-1,3-dioxolan-4-one 在 lithium diisopropyl amide 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 6.0h， 生成 格隆溴铵杂质22
  参考文献：
  名称：

  Optical Resolution, Stereoselective Synthesis, and Crystal Structure of 9α‐(3‐Azabicyclo[3,3,1]nonanyl)‐2′‐cyclopentyl‐2′‐hydroxy‐2′‐phenylacetate

  摘要：

  9 alpha-(3-Azabicyclo[3,3, 1] nonanyl)-2'-cyclopentyl-2'-hydroxy-2'-phenylacetate (1) was synthesized and its enantiomers were obtained by the optical resolution of racemates with the chiral host N-p-toluenesulfonylglutamic acid. Optical pure 1 was also effective diastereoselective synthesized using benzaldehye as steric hindrance agent from the chiral starting material, (S) or (R)-mandelic acid. The structure of the title compound was first elucidated by X-ray analysis.

  DOI：

  10.1081/scc-200057293
• 作为产物：
  描述：

  (S)-(+)-扁桃酸 、 苯甲醛 在 三氟甲磺酸 作用下， 以 正戊烷 为溶剂， 反应 24.0h， 以80%的产率得到(2S,5S)-2,5-diphenyl-1,3-dioxolan-4-one
  参考文献：
  名称：

  Optical Resolution, Stereoselective Synthesis, and Crystal Structure of 9α‐(3‐Azabicyclo[3,3,1]nonanyl)‐2′‐cyclopentyl‐2′‐hydroxy‐2′‐phenylacetate

  摘要：

  9 alpha-(3-Azabicyclo[3,3, 1] nonanyl)-2'-cyclopentyl-2'-hydroxy-2'-phenylacetate (1) was synthesized and its enantiomers were obtained by the optical resolution of racemates with the chiral host N-p-toluenesulfonylglutamic acid. Optical pure 1 was also effective diastereoselective synthesized using benzaldehye as steric hindrance agent from the chiral starting material, (S) or (R)-mandelic acid. The structure of the title compound was first elucidated by X-ray analysis.

  DOI：

  10.1081/scc-200057293

文献信息

• (α-Alkylation of α-heterosubstituted carboxylic acids without racemization
  作者：Dieter Seebach、Reto Naef、Giorgio Calderari

  DOI：10.1016/s0040-4020(01)82417-0

  日期：1984.1

  α-Hydroxy- and α-mercapto-carboxylic acids are condensed with pivalaldehyde to give 2-t-butyl-5-substituted-l,3-dioxolanones or 1,3-oxathiolanones (2); the predominate CK-isomers are separated by crystallization. The cis-disubstituted heterocycles 2 derived from lactic, mandelic and malic acid furnish, after deprotonation with LDA, reaction with electrophiles such as alkyl halides, aldehydes and ketones

  将α-羟基和α-巯基羧酸与新戊醛缩合，生成2-叔丁基-5-取代的-1,3-二氧戊环酮或1,3-氧杂硫杂环戊酮（2）；主要的CK异构体通过结晶分离。的顺式二取代的杂环2从乳酸，扁桃酸和苹果酸配料衍生，用LDA，与亲电子试剂如烷基卤化物，醛和酮，去质子化反应后，水解α-α支链羟基-羧酸（3，6，8，9，10）。这些归因于质子在α-CO位置上的整体置换而保留了构型。旋光羧酸是α-烷基化的，没有消旋作用，也没有使用手性助剂（“手性的自我复制”方案I）。非对映选择性（ds）通常> 95％（表1、2和20-25）。
• Convenient synthesis of O-functionalized mandelic acids via Lewis acid mediated transformation of 1,3-dioxolan-4-ones
  作者：Vitaly A. Shcherbinin、Valery V. Konshin

  DOI：10.1016/j.tet.2019.05.025

  日期：2019.6

  An efficient method for the synthesis of O-substituted mandelic acids containing alkenyl, alkynyl, methoxycarbonyl, or phenacyl fragments via the Lewis acid-catalyzed reaction of 1,3-dioxolan-4-ones with different C-nucleophiles is proposed.

  提出了一种有效的方法，该方法通过路易斯酸催化的1，3-二氧戊环-4-酮与不同的C-亲核试剂的反应，合成含有烯基，炔基，甲氧羰基或苯甲酰基片段的O-取代的扁桃酸。
• MASHRAQUE, S. H.;KELOGG, R. M., J. ORG. CHEM., 1984, 49, N 13, 2513-2516
  作者：MASHRAQUE, S. H.、KELOGG, R. M.

  DOI：——

  日期：——
• Optical Resolution, Stereoselective Synthesis, and Crystal Structure of 9α‐(3‐Azabicyclo[3,3,1]nonanyl)‐2′‐cyclopentyl‐2′‐hydroxy‐2′‐phenylacetate
  作者：Yan‐Qing Liu、He Liu、Bo‐hua Zhong、Yu‐Lin Deng、Ke‐liang Liu

  DOI：10.1081/scc-200057293

  日期：2005.5.1

  9 alpha-(3-Azabicyclo[3,3, 1] nonanyl)-2'-cyclopentyl-2'-hydroxy-2'-phenylacetate (1) was synthesized and its enantiomers were obtained by the optical resolution of racemates with the chiral host N-p-toluenesulfonylglutamic acid. Optical pure 1 was also effective diastereoselective synthesized using benzaldehye as steric hindrance agent from the chiral starting material, (S) or (R)-mandelic acid. The structure of the title compound was first elucidated by X-ray analysis.