cis-3,4,4a,8a-tetrahydro-8a-methylnaphthalene-1,6(2H,5H)-dione | 54584-41-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-3,4,4a,8a-tetrahydro-8a-methylnaphthalene-1,6(2H,5H)-dione
• 英文别名: dl-8aβ-Methyl-3,4,4aβ,8-tetrahydronapthalin-1(2H),6(5H)-dion；(4aR,8aR)-8a-Methyl-3,4,4a,8a-tetrahydronaphthalene-1,6(2H,5H)-dione；(4aR,8aR)-8a-methyl-3,4,4a,5-tetrahydro-2H-naphthalene-1,6-dione
• CAS: 54584-41-7
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: ODAWEHVMAKSXDW-KCJUWKMLSA-N

物化性质

• 沸点：
  307.8±31.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-3,4,4a,8a-tetrahydro-8a-methylnaphthalene-1,6(2H,5H)-dione 在 4-甲基苯磺酸吡啶 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 6.0h， 生成 rac-diethyl ((4aR,8aS)-8a-methyl-3,4,4a,8a-tetrahydro-2H-spiro[naphthalene-1,2'-[1,3]dioxolan]-6-yl) phosphate
  参考文献：
  名称：

  Regiochemistry of vinyl phosphate/.beta.-keto phosphonate rearrangements in functionalized cyclohexanones and decalones

  摘要：

  Diethyl vinyl phosphates derived from simple alkyl-substituted cyclohexanones and cyclohexenones are known to rearrange to beta-keto phosphonates upon treatment with excess LDA. To establish the effect of oxygen-containing functional groups on this transformation, vinyl phosphates containing remote carbonyl groups or acetals have been studied. The rearrangement fails in the presence of unprotected carbonyl groups but proceeds in the presence of acetals. To establish the regiochemistry of this rearrangement in fused-ring systems, representative decalins were studied. Through use of various ketones and enones, the 2- and 4-phosphono 3-keto compounds have been prepared in both cis-and trans-fused decalin series.

  DOI：

  10.1021/jo00027a055
• 作为产物：
  描述：

  (E)-methyl 3-(phenylthio)-4-(3-oxocyclohexyl)but-2-enoate 在 盐酸 、 lithium aluminium tetrahydride 、 正丁基锂 、 四丁基氢氧化铵 、 对甲苯磺酸 、 苯硫酚 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 、 苯 为溶剂， 反应 85.5h， 生成 cis-3,4,4a,8a-tetrahydro-8a-methylnaphthalene-1,6(2H,5H)-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

• Fluoride-promoted Epoxidation of α,β-Unsaturated Compounds
  作者：Masaaki Miyashita、Toshio Suzuki、Akira Yoshikoshi

  DOI：10.1246/cl.1987.285

  日期：1987.2.5

  The epoxidation of α,β-unsaturated compounds using tetrabutylammonium fluoride is described. This method has been demonstrated to be directly applicable to base-sensitive substrates such as cinnamaldehyde and α-phenylcinnamonitrile.

  四丁基氟化铵用于α,β-不饱和化合物的环氧化反应，此方法已被证明可直接应用于对碱敏感的底物，如肉桂醛和α-苯基肉桂腈。
• The organoselenium-mediated reduction of α,β-epoxy ketones, α,β-epoxy esters, and their congeners to β-hydroxy carbonyl compounds: Novel methodologies for the synthesis of aldols and their analogues
  作者：Masaaki Miyashita、Toshio Suzuki、Masahide Hoshino、Akira Yoshikoshi

  DOI：10.1016/s0040-4020(97)00781-3

  日期：1997.9

  Novel methods for the reduction of α,β-epoxy ketones, α,β-epoxy esters (glycidic esters), and their congeners to β-hydroxy carbonyl compounds (aldols) by the use of organoselenium reagents are described. The reagents, a sodium phenylseleno(triethyl)borate complex Na[PhSeB(OEt)3] easily prepared by reduction of (PhSe)2 with NaBH4 in EtOH and benzeneselenol (PhSeH) generated in situ from the borate complex

  描述了通过使用有机硒试剂将α，β-环氧酮，α，β-环氧酯（缩水甘油酯）及其同类物还原为β-羟基羰基化合物（醛醇）的新方法。通过在EtOH中用NaBH 4还原（PhSe）2和原位生成的苯硒酚（PhSeH），可以轻松制备苯基硒基（三乙基）硼酸钠复合物Na [PhSeB（OEt）3 ]通过添加乙酸从硼酸盐配合物中得到的氯已被证明可作为这些转化的极好的还原剂。有机硒介导的α，β-环氧羰基化合物在α-碳上区域特异性还原，从而以优异的收率生产出多种环状（分子内）醇醛和非环状（分子间）醇醛。定量机理研究表明，与常见的电子转移还原剂相比，有机硒介导的还原通过α取代过程进行。
• Facile and Highly Efficient Conjugate Addition of Benzeneselenol to α,β-Unsaturated Carbonyl Compounds
  作者：Masaaki Miyashita、Akira Yoshikoshi

  DOI：10.1055/s-1980-29167

  日期：——
• Diels-Alder reactions of trans-1-methoxy-3-trimethylsilyloxy-1,3-butadiene
  作者：S. Danishefsky、T. Kitahara、C. F. Yan、J. Morris

  DOI：10.1021/ja00517a036

  日期：1979.11
• Sodium phenylseleno(triethoxy)borate, Na+(PhSeB(OEt)3]−: The reactive species generated from (PhSe)2 with NaBH4 in ethanol
  作者：Masaaki Miyashita、Masahide Hoshino、Akira Yoshikoshi

  DOI：10.1016/s0040-4039(00)80092-1

  日期：1988.1