(3αS,4S,7αR)-2,2,4,7α-tetramethyl-6-(phenylsulfonyl)-3α,4,5,7α-tetrahydrobenzo[δ][1,3]dioxole | 82796-48-3

• 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: (3αS,4S,7αR)-2,2,4,7α-tetramethyl-6-(phenylsulfonyl)-3α,4,5,7α-tetrahydrobenzo[δ][1,3]dioxole
• 英文别名: (1S,2R,6S)-2,6-dimethyl-4-(phenylsulfonyl)cyclohex-3-ene-1,2-diol 1,2-diacetonide；(3aS,4S,7aR)-6-(benzenesulfonyl)-2,2,4,7a-tetramethyl-4,5-dihydro-3aH-1,3-benzodioxole
• CAS: 82796-48-3
• 化学式: C₁₇H₂₂O₄S
• 分子量: 322.425
• InChiKey: UGZIXIRIXOABMJ-YLQAJVPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3αS,4S,7αR)-2,2,4,7α-tetramethyl-6-(phenylsulfonyl)-3α,4,5,7α-tetrahydrobenzo[δ][1,3]dioxole 在 potassium osmate(VI) dihydrate 、 N-甲基吗啉氧化物 、 柠檬酸 作用下， 以 水 、 乙腈 为溶剂， 反应 30.0h， 以76%的产率得到(3αR,4R,7S,7αS)-4-hydroxy-2,2,3α,7-tetramethyltetrahydrobenzo[δ][1,3]dioxol-5(6H)-one
  参考文献：
  名称：

  Citric acid mediated catalytic osmylation/oxidative cleavage of electron deficient olefins: a vinyl sulfone study

  摘要：

  The first broad catalytic dihydroxylation of enantiopure cyclic vinyl sulfones followed by oxidative cleavage of the resulting acyloin provides linear termini-differentiated polyketide fragments. This mild vinyl sulfone cleavage provides an effective alternative to the current ozonolysis protocol. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.05.044
• 作为产物：
  描述：

  trans,cis-3,5-dimethyl-1-phenylthio-trans,cis,cis-2,3,4-trihydroxycyclohexane 3,4-acetonide 在 间氯过氧苯甲酸 、 三氯氧磷 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (3αS,4S,7αR)-2,2,4,7α-tetramethyl-6-(phenylsulfonyl)-3α,4,5,7α-tetrahydrobenzo[δ][1,3]dioxole
  参考文献：
  名称：

  Cytochalasin support studies. 5. Conjugate addition of .beta.-oxo ester dianions to vinyl sulfones: a new procedure for seven-ring annulation. Synthesis of a chiral cytochalasin C intermediate via an intramolecular Diels-Alder reaction of a chiral Z diene

  摘要：

  DOI：

  10.1021/ja00385a030

文献信息

• Scarpetti, David; Fuchs, Philip L., Journal of the American Chemical Society, 1990, vol. 112, # 22, p. 8084 - 8090
  作者：Scarpetti, David、Fuchs, Philip L.

  DOI：——

  日期：——
• Intramolecular photocyclization of aryl vinyl sulfones
  作者：C. Li、P.L. Fuchs

  DOI：10.1016/s0040-4039(00)91946-4

  日期：1993.3

  Photocyclizations of aryl vinyl sulfones at 254 nm are described. The photocyclizations proceed stereoselectively. Photochemical desufonylations of N-sulfonyl are also discussed.
• Synthesis via vinyl sulfones. 37. Cytochalasin support studies. 11. .alpha.-Silyl sulfones as latent .alpha.-sulfonyl anions. Fluoride-promoted intramolecular 1,2-additions to aldehydes as the basis of a new cyclopentenylation strategy
  作者：M. B. Anderson、P. L. Fuchs

  DOI：10.1021/jo00288a058

  日期：1990.1
• Cytochalasin support studies. 5. Conjugate addition of .beta.-oxo ester dianions to vinyl sulfones: a new procedure for seven-ring annulation. Synthesis of a chiral cytochalasin C intermediate via an intramolecular Diels-Alder reaction of a chiral Z diene
  作者：S. G. Pyne、D. C. Spellmeyer、S. Chen、P. L. Fuchs

  DOI：10.1021/ja00385a030

  日期：1982.10
• Citric acid mediated catalytic osmylation/oxidative cleavage of electron deficient olefins: a vinyl sulfone study
  作者：Thomas P. Bobinski、Philip L. Fuchs

  DOI：10.1016/j.tetlet.2015.05.044

  日期：2015.7

  The first broad catalytic dihydroxylation of enantiopure cyclic vinyl sulfones followed by oxidative cleavage of the resulting acyloin provides linear termini-differentiated polyketide fragments. This mild vinyl sulfone cleavage provides an effective alternative to the current ozonolysis protocol. (C) 2015 Elsevier Ltd. All rights reserved.