3-(phenylthio)-5,6,4a,8a-tetrahydro-5,5-dimethylnaphthalene-1,8-(4H,7H)-dione | 105090-18-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(phenylthio)-5,6,4a,8a-tetrahydro-5,5-dimethylnaphthalene-1,8-(4H,7H)-dione
• 英文别名: 3-phenylthio-5,6,4a,8a-tetrahydro-5,5-dimethyl-(4H,7H)naphthalen-1,8-dione；4,4-dimethyl-6-phenylsulfanyl-3,4a,5,8a-tetrahydro-2H-naphthalene-1,8-dione
• CAS: 105090-18-4
• 化学式: C₁₈H₂₀O₂S
• 分子量: 300.422
• InChiKey: FAKIRXZAAORPLM-UHFFFAOYSA-N

物化性质

• 熔点：
  124-126 °C(Solv: hexane (110-54-3))
• 沸点：
  445.3±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 苄基氯甲基醚 、 3-(phenylthio)-5,6,4a,8a-tetrahydro-5,5-dimethylnaphthalene-1,8-(4H,7H)-dione 生成 8a-<<(benzyloxy)methoxy>methyl>-5,5-dimethyl-3-(phenylthio)-4a,5,6,8a-tetrahydronaphthalene-1,8(4H,7H)-dione
  参考文献：
  名称：

  Angular hydroxymethylation of functionalized decalin systems

  摘要：

  Functionalized beta-dicarbonyl bicyclic compounds 5 and 17 were hydroxymethylated at the angular position as the (benzyloxy)methoxy derivatives with diisopropylethylamine (DIPEA) and benzyl chloromethyl ether in the presence of paraformaldehyde. The stereochemistry of cis-8a-[[(benzyloxy)methoxy]methyl]-3-(phenylthio)-4a,5,6,8a-tetrahydronaphthalene-1,8(4H,7H)-dione (12) was confirmed by X-ray analysis of the ethylene ketal 16.

  DOI：

  10.1021/jo00010a023
• 作为产物：
  描述：

  4,4-二甲基-2-环己基-1-酮 在 potassium tert-butylate 、 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 3-(phenylthio)-5,6,4a,8a-tetrahydro-5,5-dimethylnaphthalene-1,8-(4H,7H)-dione
  参考文献：
  名称：

  A new 4C + 2C annelation reaction based on tandem Michael-Claisen condensation. 1. General scope

  摘要：

  DOI：

  10.1021/jo00377a020

文献信息

• A new 4C + 2C annelation reaction based on tandem Michael-Claisen condensation. 1. General scope
  作者：Tak Hang Chan、C. V. C. Prasad

  DOI：10.1021/jo00377a020

  日期：1987.1
• CHAN, T. H.;SCHWERDTFEGER, A. E., J. ORG. CHEM., 56,(1991) N0, C. 3294-3298
  作者：CHAN, T. H.、SCHWERDTFEGER, A. E.

  DOI：——

  日期：——
• CHAN TAK HANG; PRASAD C. V. C., J. ORG. CHEM., 52,(1987) N 1, 110-119
  作者：CHAN TAK HANG、 PRASAD C. V. C.

  DOI：——

  日期：——
• Chan, T. H.; Guertin, K. R.; Prasad, C. V. C., Canadian Journal of Chemistry, 1990, vol. 68, # 7, p. 1170 - 1177
  作者：Chan, T. H.、Guertin, K. R.、Prasad, C. V. C.、Thomas, A. W.、Strunz, G. M.、Salonius, A.

  DOI：——

  日期：——
• Angular hydroxymethylation of functionalized decalin systems
  作者：T. H. Chan、A. E. Schwerdtfeger

  DOI：10.1021/jo00010a023

  日期：1991.5

  Functionalized beta-dicarbonyl bicyclic compounds 5 and 17 were hydroxymethylated at the angular position as the (benzyloxy)methoxy derivatives with diisopropylethylamine (DIPEA) and benzyl chloromethyl ether in the presence of paraformaldehyde. The stereochemistry of cis-8a-[[(benzyloxy)methoxy]methyl]-3-(phenylthio)-4a,5,6,8a-tetrahydronaphthalene-1,8(4H,7H)-dione (12) was confirmed by X-ray analysis of the ethylene ketal 16.