7-(2',2'-dimethylpropylenedioxy)-6-methylbicyclo[4.4.0]-1-decen-3-one | 42829-94-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-(2',2'-dimethylpropylenedioxy)-6-methylbicyclo[4.4.0]-1-decen-3-one
• 英文别名: 1,1-(2,2-Dimethylpropan-1,3-diyldioxy)-6-oxo-8a-methyl-Δ^4a(5)-octalin；4'a,5,5-trimethylspiro[1,3-dioxane-2,5'-4,6,7,8-tetrahydro-3H-naphthalene]-2'-one
• CAS: 42829-94-7
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: SDWKIHTZBFGXEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  19.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  7-(2',2'-dimethylpropylenedioxy)-6-methylbicyclo[4.4.0]-1-decen-3-one 在 盐酸 、 正丁基锂 、 lithium 、 L-Selectride 、 臭氧 、 溶剂黄146 、 N,N-二异丙基乙胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 氨 、 丙酮 为溶剂， 生成 trans-acetonyl-2 decahydro-1,2,3,4,4a,5,6,7,8,8a (methoxy-2 ethoxy methoxy)-6α methyl-8aβ naphtalene
  参考文献：
  名称：

  A→B→C→D型C-或D-类固醇的全合成，包括用于构建D环的还原性烷基化步骤

  摘要：

  外消旋C-也不d-homosteroid化合物的立体有择全合成，其具有六个不对称碳原子和其中介绍的自然- -结构，在从维兰德-米舍尔酮开始12个步骤进行。

  DOI：

  10.1016/s0040-4039(00)84593-1
• 作为产物：
  描述：

  9-甲基-delta-5(10)-辛-1,6-二酮 、 2,2-二甲基-1,3-丙二醇 在 三氟化硼乙醚 作用下， 生成 7-(2',2'-dimethylpropylenedioxy)-6-methylbicyclo[4.4.0]-1-decen-3-one
  参考文献：
  名称：

  A→B→C→D型C-或D-类固醇的全合成，包括用于构建D环的还原性烷基化步骤

  摘要：

  外消旋C-也不d-homosteroid化合物的立体有择全合成，其具有六个不对称碳原子和其中介绍的自然- -结构，在从维兰德-米舍尔酮开始12个步骤进行。

  DOI：

  10.1016/s0040-4039(00)84593-1

文献信息

• Design and synthesis of intramolecular ion-pairing cis-bicyclo[4.4.0]decane (cis-decalin) amino acids: conformation-based probes of electrostatic interactions in water
  作者：Craig Beeson、Thomas A. Dix

  DOI：10.1021/jo00042a015

  日期：1992.7

  The design strategy and synthesis of cis-bicyclo[4.4.0]decane (cis-decalin) derivatives as conformation-based probes of electrostatic interactions in H2O are described. The molecules were designed so that formation of an intramolecular electrostatic interaction occurs in only one of two low-energy conformers; hence, the conformational equilibrium of a given molecule is under control of the electrostatic interaction, which can be determined accurately with NMR studies. The structural definition inherent to the molecules will enable the thermodynamics and kinetics of solvent reorganization, which controls formation of electrostatic interactions in H2O, to be probed directly. The first probe, a cis-decalin amino acid designed to evaluate an intramolecular ion pair, has been synthesized. The total synthesis was efficient and illustrated many of the strategies and potential pitfalls associated with the preparation of conformationally flexible ring systems. In particular, the inherent facial selectivity afforded by the shape of the cis-decalin, a critical component of the synthetic design, was reversed in one step in which hydrogen was added from the sterically encumbered concave face of the molecule. A cis-decalin amino acid of a different stereoelectronic array was also prepared. These molecules are the first examples to emerge from the application of a general design and synthetic strategy that will enable probes for all of the important biological electrostatic interactions to be constructed. The study of these molecules will provide significant insight into the synergistic role of molecular structure and solvent at controlling electrostatic interactions in H2O, an important basis of biological structure and function.
• Yajima, Arata; Mori, Kenji, European Journal of Organic Chemistry, 2000, # 24, p. 4079 - 4091
  作者：Yajima, Arata、Mori, Kenji

  DOI：——

  日期：——
• A Useful Synthesis of 1,6-Dioxo-8a-methyl-<i>trans</i>-Δ⁷-octalin: An Isomer of Wieland-Miescher Ketone
  作者：Geetha Gopalakrishnan、S. Jayaraman、K. Rajagopalan、S. Swaminathan

  DOI：10.1055/s-1983-30517

  日期：——