cis-1-Hydroxy-6-methylbicyclo<4.3.0>nonane | 144126-86-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-1-Hydroxy-6-methylbicyclo<4.3.0>nonane
• 英文别名: cis-5-methylbicyclo<4.3.0>nonan-1-ol；cis-octahydro-7a-methyl-3aH-inden-3a-ol；cis-1-Hydroxy-6-methylbicyclo[4.3.0]nonane；(3aS,7aS)-7a-methyl-2,3,4,5,6,7-hexahydro-1H-inden-3a-ol
• CAS: 144126-86-3；101493-15-6
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: MCHHSFBWPODKAS-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cis-1-Hydroxy-6-methylbicyclo<4.3.0>nonane 在 碘 、 mercury(II) oxide 作用下， 以 四氯化碳 为溶剂， 反应 1.0h， 以22%的产率得到2-iodo-6-methyl-6(Z)-cyclononenone
  参考文献：
  名称：

  .beta.-Scission of 8-hydrindanoxyl and related free radicals

  摘要：

  DOI：

  10.1021/jo00257a006
• 作为产物：
  描述：

  3-(1-methyl-2-oxocyclohexyl)propanenitrile 在 lithium aluminium tetrahydride 、 四乙基对甲苯磺酸铵 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 9.0h， 生成 cis-1-Hydroxy-6-methylbicyclo<4.3.0>nonane
  参考文献：
  名称：

  Electroorganic chemistry. 140. Electroreductively promoted intra- and intermolecular couplings of ketones with nitriles.

  摘要：

  Electroreduction of gamma and delta-cyano ketones in i-PrOH with Sn cathode gave alpha-hydroxy ketones and their dehydroxylated ketones as the intramolecularly coupled products. Guaiazulene, (-)-valeranone, polyquinanes, dihydrojasmone, methyl dihydrojasmonate, and rosaprostol have been synthesized by utilizing this electroreductive intramolecular coupling of gamma and delta-cyano ketones in one of the key steps. Similarly, electroreduction of a mixture of ketone and nitrile gave the corresponding intermolecularly coupled product. The product obtained by the electroreductive intermolecular coupling of (+)-dihydrocarvone with acetonitrile has been found to be the precursor of an effective chiral ligand for the enantioselective addition of diethylzinc to aldehydes.

  DOI：

  10.1021/jo00052a036

文献信息

• Electroorganic chemistry. 124. Electroreductive intramolecular coupling of .alpha.-(.omega.-bromoalkyl) .beta.-keto esters
  作者：Tatsuya Shono、Naoki Kise、Nobuyuki Uematsu、Shinji Morimoto、Eiichi Okazaki

  DOI：10.1021/jo00304a014

  日期：1990.8
• Lanthanides in organic synthesis. 3. A general procedure for five- and six-membered ring annulation
  作者：Gary A. Molander、Jeffrey B. Etter

  DOI：10.1021/jo00360a025

  日期：1986.5
• Carbonyl-initiated cyclization of tetraalkylstannanes
  作者：Timothy L. Macdonald、Claire M. Delahunty、Keith Mead、Dale E. O'Dell

  DOI：10.1016/s0040-4039(00)99494-2

  日期：1989.1
• Electroorganic chemistry. 140. Electroreductively promoted intra- and intermolecular couplings of ketones with nitriles.
  作者：Tatsuya Shono、Naoki Kise、Taku Fujimoto、Naoto Tominaga、Hiroshi Morita

  DOI：10.1021/jo00052a036

  日期：1992.12

  Electroreduction of gamma and delta-cyano ketones in i-PrOH with Sn cathode gave alpha-hydroxy ketones and their dehydroxylated ketones as the intramolecularly coupled products. Guaiazulene, (-)-valeranone, polyquinanes, dihydrojasmone, methyl dihydrojasmonate, and rosaprostol have been synthesized by utilizing this electroreductive intramolecular coupling of gamma and delta-cyano ketones in one of the key steps. Similarly, electroreduction of a mixture of ketone and nitrile gave the corresponding intermolecularly coupled product. The product obtained by the electroreductive intermolecular coupling of (+)-dihydrocarvone with acetonitrile has been found to be the precursor of an effective chiral ligand for the enantioselective addition of diethylzinc to aldehydes.
• .beta.-Scission of 8-hydrindanoxyl and related free radicals
  作者：Dale E. O'Dell、John T. Loper、Timothy L. Macdonald

  DOI：10.1021/jo00257a006

  日期：1988.10