(+)-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone | 38772-79-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone
• 英文别名: (4aS)-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one；4,4a,5,6,7,8-Hexahydro-naphthalin-3H-2-on；(4aS)-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one
• CAS: 38772-79-1
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: FOCKPZOFYCTNIA-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+)-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 苯 为溶剂， 反应 72.5h， 生成 (S)-1,2,3,5,6,7,8,8a-Octahydro-naphthalene-2,3-diol
  参考文献：
  名称：

  Modeling the Effect of Substitution on the Pb(OAc)₄ Mediated Oxidative Cleavage of Steroidal 1,2-Diols

  摘要：

  We comment on the effects of angular substitution on the outcome of a Pb(OAc)(4) (LTA) mediated heterodomino reaction, with selected bicyclic unsaturated 1,2-diols, which is considered to proceed through a series of transformations in a single vessel. The first two, oxidative and pericyclic, are followed by the key step, an electrophilic addition of LTA to the olefin, responsible for the course of the domino process. In this study, the electrophilic addition of LTA to the double bond has been modeled with B3LYP, where the 6-31G* basis set is used for C, 0, and H atoms and the LANL2DZ method is used for Pb. The modeling in the gaseous phase and in solution has revealed the concerted nature of the addition of LTA to the double bond of the intermediate. The fact that LTA adds from the same side as the substituent R, for R=H and from the opposite side when R=CH3 has been attributed to steric hindrance, which causes deformation of the olefinic intermediate.

  DOI：

  10.1021/jo0505627
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 (+)-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone
  参考文献：
  名称：

  Enantioselectivity of microbial hydrolysis of (.+-.)-decahydro-2-naphthyl acetates. Preparations and absolute configurations of chiral decahydro-2-naphthols

  摘要：

  DOI：

  10.1021/jo00194a004

文献信息

• PHILIPPO, CHRISTOPHE M. G.;VO, NHA NUU;PAGUETTE, LEO A., J. AMER. CHEM. SOC., 113,(1991) N, C. 2762-2764
  作者：PHILIPPO, CHRISTOPHE M. G.、VO, NHA NUU、PAGUETTE, LEO A.

  DOI：——

  日期：——
• ORITANI, TAKAYUKI;YAMASHITA, KYOHEI;KABUTO, CHIZUKO, J. ORG. CHEM., 1984, 49, N 20, 3689-3694
  作者：ORITANI, TAKAYUKI、YAMASHITA, KYOHEI、KABUTO, CHIZUKO

  DOI：——

  日期：——
• HUTCHINSON, D. K.;FUCHS, P. L., J. AMER. CHEM. SOC., 109,(1987) N 16, 4930-4939
  作者：HUTCHINSON, D. K.、FUCHS, P. L.

  DOI：——

  日期：——
• Modeling the Effect of Substitution on the Pb(OAc)₄ Mediated Oxidative Cleavage of Steroidal 1,2-Diols
  作者：C. Öztürk、K. Topal、V. Aviyente、Nurcan Ş. Tüzün、E. Sánchez Fernández、S. Arseniyadis

  DOI：10.1021/jo0505627

  日期：2005.9.1

  We comment on the effects of angular substitution on the outcome of a Pb(OAc)(4) (LTA) mediated heterodomino reaction, with selected bicyclic unsaturated 1,2-diols, which is considered to proceed through a series of transformations in a single vessel. The first two, oxidative and pericyclic, are followed by the key step, an electrophilic addition of LTA to the olefin, responsible for the course of the domino process. In this study, the electrophilic addition of LTA to the double bond has been modeled with B3LYP, where the 6-31G* basis set is used for C, 0, and H atoms and the LANL2DZ method is used for Pb. The modeling in the gaseous phase and in solution has revealed the concerted nature of the addition of LTA to the double bond of the intermediate. The fact that LTA adds from the same side as the substituent R, for R=H and from the opposite side when R=CH3 has been attributed to steric hindrance, which causes deformation of the olefinic intermediate.
• Enantioselectivity of microbial hydrolysis of (.+-.)-decahydro-2-naphthyl acetates. Preparations and absolute configurations of chiral decahydro-2-naphthols
  作者：Takayuki Oritani、Kyohei Yamashita、Chizuko Kabuto

  DOI：10.1021/jo00194a004

  日期：1984.10