(2S,4aR,8aS)-decahydro-2-naphthol | 54324-61-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4aR,8aS)-decahydro-2-naphthol
• 英文别名: (-)-cis,cis-decahydro-2-naphthol；(4ar,8ac)-decahydro-naphthalen-2t-ol；1.2.3.4.4αβ.5.6.7.8.8αβ-Decahydronaphthalin-2α-ol；2α-Hydroxy-trans-decalin；cis-cis-Decalol-(2)；cis-2trans-Dekalol；cis-Decahydro-naphthalen-2-ol；(2S,4aR,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-ol
• CAS: 54324-61-7
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: UPMAOXLCTXPPAG-UTLUCORTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  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：

  (2S,4aR,8aS)-decahydro-2-naphthol 以91%的产率得到
  参考文献：
  名称：

  Thompson Hugh W., Gaglani Kamlesh D., J. Chem. Soc. PerKin Trans. 2, (1993) N 5, S 967-972

  摘要：

  DOI：
• 作为产物：
  描述：

  [(4aS,8aR)-1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-yl] acetate 以43%的产率得到
  参考文献：
  名称：

  ORITANI, TAKAYUKI;YAMASHITA, KYOHEI;KABUTO, CHIZUKO, J. ORG. CHEM., 1984, 49, N 20, 3689-3694

  摘要：

  DOI：

文献信息

• Herbicidal 1,2,4,6-thiatriazines
  申请人：Syngenta Investment Corporation

  公开号：US06362134B1

  公开（公告）日：2002-03-26

  Compounds of formula (I), in which R1, R2 and R3 are as defined in claim 1, are particularly suitable as herbicides.

  式（I）中的化合物，其中R1、R2和R3如权利要求1所定义，特别适用作为除草剂。
• Synthesis and Pseudomonas Lipase Inhibition Study of Stereoisomers of Decahydro-2-naphthyl-N-n-butylcarbamate
  作者：Ming-Cheng Lin、Yu-Fang Shen、Gialih Lin

  DOI：10.2174/092986611797200913

  日期：2011.11.1

  (2S,4aR,8aS)-Cis,cis-, (2R,4aS,8aR)-cis,cis-, rac-cis,cis-, and rac-trans,cis-decahydro-2-naphthyl-N-n-butylcarbamates are synthesized from condensation of (2S,4aR,8aS)-cis,cis-, (2R,4aS,8aR)-cis,cis-, rac-cis,cis-, and rac-trans,cisdecahydro- 2-naphthols, respectively, with n-butyl isocyanate in the presence of triethylamine in dichloromethane. Optically pure (2S,4aR,8aS)-(-)- and (2R,4aS,8aR)-(+)-cis,cis-decahydro-2-naphthols are resolved by the porcine pancreatic lipase- catalyzed acetylation of decahydro-2-naphthols with vinyl acetate in t-butyl methyl ether. Absolute configurations of (2S,4aR,8aS)-(-)- and (2R,4aS,8aR)-(+)- cis,cis-decahydro-2-naphthols are determined from the 19F NMR spectra of their Moshers ester derivatives. (2S,4aR,8aR)-Trans,cis- and (2R,4aS,8aS)-trans,cis-decahydro-2-naphthols cant be resolved from the porcine pancreatic lipase-catalyzed acetylation of decahydro-2-naphthols with vinyl acetate in t-butyl methyl ether. For the inhibitory potency of Pseudomonas lipase, (2S,4aR,8aS)-cis,cis-decahydro-2-naphthyl-N-n-butylcarbamate is 3.5 times more potent than (2R,4aS,8aR)-cis,cis-decahydro-2-naphthyl-N-n-butylcarbamate; racemic cis,cis-decahydro- 2-naphthyl-N-n-butylcarbamate is about the same with trans,cis-decahydro-2-naphthyl-N-n-butylcarbamate. These inhibitors also show similar effects on porcine pancreatic lipase.

  (2S,4aR,8aS)-Cis,cis-、(2R,4aS,8aR)-cis,cis-、rac-cis,cis-和rac-trans,cis-十氢-2-萘基-N-正丁基氨基甲酸酯是分别由(2S，4aR，8aS)-顺式，顺式-，(2R，4aS，8aR)-顺式，顺式-，rac-顺式，顺式-和rac-反式，顺式十氢-2-萘酚缩合合成，在三乙胺存在下，在二氯甲烷中与异氰酸正丁酯反应。光学纯的 (2S,4aR,8aS)-(-)- 和 (2R,4aS,8aR)-(+)-cis,cis-decaHydro-2-naphthols 通过猪胰脂肪酶催化的 decaHydro-2 乙酰化来解析-萘酚与乙酸乙烯酯在叔丁基甲基醚中的反应。 (2S,4aR,8aS)-(-)-和(2R,4aS,8aR)-(+)-顺式,顺式十氢-2-萘酚的绝对构型由它们的Moshers酯衍生物的19F NMR谱确定。 (2S,4aR,8aR)-Trans,cis- 和 (2R,4aS,8aS)-trans,cis-deca Hydro-2-naphthols 不能从猪胰脂肪酶催化的十氢-2-萘酚与乙酸乙烯酯的乙酰化中分离出来在叔丁基甲基醚中。对于假单胞菌脂肪酶的抑制效力，(2S,4aR,8aS)-cis,cis-decaHydro-2-naphthyl-N-n-丁基氨基甲酸酯的抑制效力是 (2R,4aS,8aR)-cis,cis-decaHydro-2 的 3.5 倍-萘基-N-正丁基氨基甲酸酯；外消旋顺式，顺式十氢-2-萘基-N-正丁基氨基甲酸酯与反式，顺式-十氢-2-萘基-N-正丁基氨基甲酸酯大致相同。这些抑制剂对猪胰脂肪酶也显示出类似的作用。
• Selective and stereospecific enzyme-catalysed reductions of cis-and trans-decalindiones to enantiomerically pure hydroxy-ketones; an efficient access to (+)-4-twistanone
  作者：David R. Dodds、J. Bryan Jones

  DOI：10.1039/c39820001080

  日期：——

  preparative-scale horse liver alcohol dehydrogenase-catalysed reductions of highly symmetrical cis-and trans-decalindiones are effected regio-and stereo-specifically on only one of the two carbonyl groups to give enantiomerically pure hydroxy-ketones of predictable configurations and of broad values as chiral synthons, as exemplified by the synthesis of (+)-(4R)-twistanone from cis-decalin-2,7-dione

  制备规模的马肝酒精脱氢酶催化的高度对称的顺式和反式十氢吲哚还原反应仅在两个羰基基团中的一个区域上进行立体和立体定向，从而得到对映体纯的羟基酮，具有可预测的构型和广泛的应用价值手性合成子，例如由顺式十氢化萘-2,7-二酮以51％的总产率合成（+）-（4R）-twistanone 。
• 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