8β-Hydroxy-4aβ-methyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one | 87262-14-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8β-Hydroxy-4aβ-methyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one
• 英文别名: 8β-hydroxy-10-methyl-Δ^1,9-2-octalone；(4aR,8S)-8-hydroxy-4a-methyl-3,4,5,6,7,8-hexahydronaphthalen-2-one
• CAS: 87262-14-4
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: SLEYQMLVMGAGDK-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8β-Hydroxy-4aβ-methyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one 在 lithium 作用下， 以 四氢呋喃 、 氨 为溶剂， 生成 4a-methyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-2-one
  参考文献：
  名称：

  Reductive alkylation of enediones. 1

  摘要：

  DOI：

  10.1021/ja00523a078
• 作为产物：
  描述：

  4A-甲基-4,4a,5,6,7,8-六氢-3H-萘-2-酮 在 sodium hydroxide 、 间氯过氧苯甲酸 作用下， 生成 8β-Hydroxy-4aβ-methyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one
  参考文献：
  名称：

  The Mechanism of the Microbial Hydroxylation of Steroids. Part 2. Hydroxylation of a Δ⁴-3-Ketosteroid Analog by Rhizopus arrhizus ATCC 11145

  摘要：

  Δ4-3-酮类固醇类似物（±）-4a-甲基-4,4a,5,6,7,8-六氢-2（3H）萘酮（1）被Rhizopusarrhizus ATCC 11145在C-8α和C-8β两个位置羟化。将C-8α与C-8β羟化的比率与2-乙氧基-4a-甲基-3,4,4a,5,6,7-六氢萘（4）的过酸化反应得到的比率进行比较，并提出了一种微生物和化学羟化的机理，其中产物的立体化学是过渡态控制的。讨论了这对微生物C-6β羟化的机理的意义。

  DOI：

  10.1139/v75-284

文献信息

• The Mechanism of the Microbial Hydroxylation of Steroids. Part 2. Hydroxylation of a Δ⁴-3-Ketosteroid Analog by <i>Rhizopus arrhizus</i> ATCC 11145
  作者：Herbert L. Holland、Barbara J. Auret

  DOI：10.1139/v75-284

  日期：1975.7.15

  The Δ⁴-3-ketosteroid analog (± )-4a-methyl-4,4a,5,6,7,8-hexahydro-2(3H) naphthalenone (1) is hydroxylated at both C-8α and C-8β by Rhizopusarrhizus ATCC 11145. The ratio of C-8α to C-8β hydroxylation is compared with that obtained from the peracid oxidation of 2-ethoxy-4a-methyl-3,4,4a,5,6,7-hexahydronaphthalene (4) and a mechanism is proposed for both microbial and chemical hydroxylation in which the stereochemistry of the product is transition state controlled. The significance of this to the mechanism of microbial C-6β hydroxylation of Δ⁴-3-ketosteroids is discussed.

  Δ4-3-酮类固醇类似物（±）-4a-甲基-4,4a,5,6,7,8-六氢-2（3H）萘酮（1）被Rhizopusarrhizus ATCC 11145在C-8α和C-8β两个位置羟化。将C-8α与C-8β羟化的比率与2-乙氧基-4a-甲基-3,4,4a,5,6,7-六氢萘（4）的过酸化反应得到的比率进行比较，并提出了一种微生物和化学羟化的机理，其中产物的立体化学是过渡态控制的。讨论了这对微生物C-6β羟化的机理的意义。
• Parvez, Aslam; Hanson, James R., Journal of Chemical Research, 2004, # 9, p. 647 - 648
  作者：Parvez, Aslam、Hanson, James R.

  DOI：——

  日期：——
• Microbial hydroxylation and functionalization of synthetic polycyclic enones
  作者：Abderrahmane Hammoumi、Jean-Pierre Girault、Robert Azerad、Gilbert Revial、Jean d'Angelo

  DOI：10.1016/s0957-4166(00)80241-4

  日期：1993.6

  The regio- and stereoselective hydroxylation of variously substituted asymmetric 4a-methyl octalenones by selected fungal strains has been shown to afford, sometimes in high yields, several optically pure derivatives, generally hydroxylated in the B-ring. The potential of this method for the preparation of functionalized (hydroxylated) chiral synthons is evaluated and discussed.
• Microbial hydroxylation and functionalization of synthetic bicyclic enones
  作者：A. Hammoumi、G. Revial、J. D'Angelo、J.P. Girault、R. Azerad

  DOI：10.1016/s0040-4039(00)74851-9

  日期：1991.1

  The regio- and stereoselective hydroxylation of substituted octalones by various fungal strains has been evaluated. Several hydroxylated derivatives have been obtained and the potential of this method for the preparation of useful chiral synthons is discussed.
• Studies on the Biosynthesis of Taxol: Total Synthesis of Taxa-4(20),11(12)-diene and Taxa-4(5),11(12)-diene. The First Committed Biosynthetic Intermediate
  作者：Steven M. Rubenstein、Robert M. Williams

  DOI：10.1021/jo00127a029

  日期：1995.11

  The total synthesis of taxa-4(20),11(12)-diene and taxa-4(5),11(12)-diene is described.